2211:
1735:
2206:{\displaystyle {\underbrace {\ce {H-\!\!{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!\!\!:}} _{\text{amine}}+\underbrace {\ce {R3-{\overset {\displaystyle O \atop \|}{C}}-OH}} _{\text{carboxylic acid}}->}\ \underbrace {\ce {{H-{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N+}}}-H}+R3-COO^{-}}} _{{\text{substituted-ammonium}} \atop {\text{carboxylate salt}}}{\ce {->}}{\underbrace {\ce {{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!-{\overset {\displaystyle O \atop \|}{C}}-R3}} _{\text{amide}}+\underbrace {\ce {H2O}} _{\text{water}}}}
1692:
320:
313:
4571:
58:
327:
664:
518:
501:
694:: the nitrogen center bears four substituents counting the lone pair. Because of the low barrier to inversion, amines of the type NHRR' cannot be obtained in optical purity. For chiral tertiary amines, NRRâ˛Râł can only be resolved when the R, R', and Râł groups are constrained in cyclic structures such as
1094:
Solvation significantly affects the basicity of amines. N-H groups strongly interact with water, especially in ammonium ions. Consequently, the basicity of ammonia is enhanced by 10 by solvation. The intrinsic basicity of amines, i.e. the situation where solvation is unimportant, has been evaluated
641:
primary amines exhibit two N-H bands, whereas secondary amines exhibit only one. In their IR spectra, primary and secondary amines exhibit distinctive N-H stretching bands near 3300 cm. Somewhat less distinctive are the bands appearing below 1600 cm, which are weaker and overlap with C-C and C-H
3776:
are also widely used in this capacity. The reaction proceeds by the lone pair of electrons on the amine nitrogen attacking the outermost carbon on the oxirane ring of the epoxy resin. This relieves ring strain on the epoxide and is the driving force of the reaction. Molecules with tertiary amine
1095:
in the gas phase. In the gas phase, amines exhibit the basicities predicted from the electron-releasing effects of the organic substituents. Thus tertiary amines are more basic than secondary amines, which are more basic than primary amines, and finally ammonia is least basic. The order of pK
1085:
Owing to inductive effects, the basicity of an amine might be expected to increase with the number of alkyl groups on the amine. Correlations are complicated owing to the effects of solvation which are opposite the trends for inductive effects. Solvation effects also dominate the basicity of
4880:
1086:
aromatic amines (anilines). For anilines, the lone pair of electrons on nitrogen delocalizes into the ring, resulting in decreased basicity. Substituents on the aromatic ring, and their positions relative to the amino group, also affect basicity as seen in the table.
4077:
4235:
Kaljurand, I.; Kßtt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent
Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales".
2940:
714:
In aromatic amines ("anilines"), nitrogen is often nearly planar owing to conjugation of the lone pair with the aryl substituent. The C-N distance is correspondingly shorter. In aniline, the C-N distance is the same as the C-C distances.
1321:
In such reactions, which are more useful for alkyl iodides and bromides, the degree of alkylation is difficult to control such that one obtains mixtures of primary, secondary, and tertiary amines, as well as quaternary ammonium salts.
3800:
between 100 and 1000 mg/kg. They are skin irritants, especially as some are easily absorbed through the skin. Amines are a broad class of compounds, and more complex members of the class can be extremely bioactive, for example
632:
Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. H NMR signals for amines disappear upon treatment of the sample with
4779:
Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 12, Chapter 1.3.1 Master of
Science Thesis April 1997 Imperial College
248:
The chemical notation for amines contain the letter "R", where "R" is not an element, but a "R-group" which means "rest of the molecule" and in amines could be a single hydrogen or carbon atom, or could be a hydrocarbon chain.
4069:
2682:
1114:
the energy of solvation is not as high as in protic polar solvents like water and methanol. For this reason, the basicity of amines in these aprotic solvents is almost solely governed by the electronic effects.
3129:
2778:
2435:
3494:
derived from the modification of amino acids are referred to as amine hormones. Typically, the original structure of the amino acid is modified such that a âCOOH, or carboxyl, group is removed, whereas the
3532:. It reacts with nitrous acid to form diazonium salt, which can undergo coupling reaction to form an azo compound. As azo-compounds are highly coloured, they are widely used in dyeing industries, such as:
1316:
1206:
675:
Alkyl amines characteristically feature tetrahedral nitrogen centers. C-N-C and C-N-H angles approach the idealized angle of 109°. C-N distances are slightly shorter than C-C distances. The
2308:
2525:
1447:) and its derivatives are prepared by reduction of the nitroaromatics. In industry, hydrogen is the preferred reductant, whereas, in the laboratory, tin and iron are often employed.
2322:
to give diazonium salts. The alkyl diazonium salts are of little importance because they are too unstable. The most important members are derivatives of aromatic amines such as
4654:
Hammer, Georg; LĂźbcke, Torsten; Kettner, Roland; Davis, Robert N.; Recknagel, Herta; Commichau, Axel; Neumann, Hans-Joachim; Paczynska-Lahme, Barbara (2000). "Natural Gas".
1099:'s (basicities in water) does not follow this order. Similarly aniline is more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.
4585:
Betts, J Gordon; Desaix, Peter; Johnson, Eddie; Johnson, Jody E; Korol, Oksana; Kruse, Dean; Poe, Brandon; Wise, James; Womble, Mark D; Young, Kelly A (26 July 2023).
3874:
2789:
624:
into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Their boiling points are high and their solubility in water is low.
4942:
397:âSecondary amines have two organic substituents (alkyl, aryl or both) bound to the nitrogen together with one hydrogen. Important representatives include
4026:
3987:
1361:
4610:
Roughley, Stephen D.; Jordan, Allan M. (2011). "The
Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates".
2962:
575:
involving these lone electron pairs. Typically salts of ammonium compounds exhibit the following order of solubility in water: primary ammonium (
3705:
2572:
1386:, unsaturated N-containing functional groups are reduced to amines using hydrogen in the presence of a nickel catalyst. Suitable groups include
6524:
4158:
G. M. WĂłjcik "Structural
Chemistry of Anilines" in Anilines (Patai's Chemistry of Functional Groups), S. Patai, Ed. 2007, Wiley-VCH, Weinheim.
2444:
salts, which can be isolated in the crystalline form. Diazonium salts undergo a variety of useful transformations involving replacement of the
667:
Inversion of an amine spatial configuration: Amine "flip-flop" like an umbrella turned over by the wind. The pair of dots represents the lone
6548:
6540:
5932:
3919:
2687:
1216:
Unlike the reaction of amines with alcohols the reaction of amines and ammonia with alkyl halides is used for synthesis in the laboratory:
1344:
Aryl halides are much less reactive toward amines and for that reason are more controllable. A popular way to prepare aryl amines is the
4973:
3612:, an antipsychotic drug, is an amine which is believed to exhibit its antipsychotic effects, in part, due to its effects on other amines.
1612:
3844:
1356:
Disubstituted alkenes react with HCN in the presence of strong acids to give formamides, which can be decarbonylated. This method, the
3897:
3578:
is a tranquilizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.
5892:
2332:
1553:
This reaction is valid for preparation of primary amines only. Gives good yields of primary amines uncontaminated with other amines.
3472:
4792:"Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin"
196:
group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one
5897:
1725:. When formed from carboxylic acids and primary and secondary amines, these salts thermally dehydrate to form the corresponding
4100:
552:
alcohols are liquids. Amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" and foul smell.
514:
as a functional group. IUPAC however does not recommend this convention, but prefers the alkanamine form, e.g. butan-2-amine.
4910:
4594:
4286:
4038:
3778:
4301:
Weiberth, Franz J.; Hall, Stan S. (1986). "Tandem alkylation-reduction of nitriles. Synthesis of branched primary amines".
3781:. It has been stated that this is the most widely used room temperature accelerator for two-component epoxy resin systems.
474:
Amines are named in several ways. Typically, the compound is given the prefix "amino-" or the suffix "-amine". The prefix "
4452:
Andrade, Miguel A.; O'Donoghue, SeĂĄn I.; Rost, Burkhard (1998). "Adaptation of protein surfaces to subcellular location".
1222:
4129:
3471:
is typically bound to various amine-rich proteins. Additionally, the terminal charged primary ammonium on lysine forms
1406:. In the case of nitriles, reactions are sensitive to acidic or alkaline conditions, which can cause hydrolysis of the
1138:
4510:
4436:
4340:
4192:
3957:
3294:
2230:
2461:
687:
for a trialkylamine. The interconversion has been compared to the inversion of an open umbrella into a strong wind.
5925:
2546:
4966:
3603:
1505:
4839:"Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator"
4386:
Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2000). "Azo Dyes".
1607:
4939:
4764:
4671:
4403:
4004:
1621:
17:
5796:
3168:
1685:
4934:
4044:
3652:
and secondary amines. (The tricyclics are grouped by the nature of the final amino group on the side chain.)
458:
It is also possible to have four organic substituents on the nitrogen. These species are not amines but are
1069:
The electronic properties of the substituents (alkyl groups enhance the basicity, aryl groups diminish it).
3777:
functionality are often used to accelerate the epoxy-amine curing reaction and include substances such as
5918:
4276:
3208:
4644:
American
Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2510
4575:
567:
NH. The lone electron pair is represented in this article by two dots above or next to the N. The water
6636:
5369:
4959:
4428:
3659:
3287:
478:-" shows substitution on the nitrogen atom. An organic compound with multiple amino groups is called a
459:
438:
amines are either secondary or tertiary amines. Examples of cyclic amines include the 3-membered ring
3649:
3572:
that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings.
1691:
1483:
1411:
1345:
427:
A fourth subcategory is determined by the connectivity of the substituents attached to the nitrogen:
319:
5406:
4466:
3768:, and a variety of diamines such as 4,4-diaminodicyclohexylmethane. Multifunctional amines such as
3631:
1563:
703:
1455:
Many methods exist for the preparation of amines, many of these methods being rather specialized.
5879:
3717:
3232:
312:
3923:
1370:
Hydroamination of alkenes is also widely practiced. The reaction is catalyzed by zeolite-based
6427:
5972:
5779:
4712:
Howarth, Graham (1 January 1995). "The use of water-based epoxies for anti-corrosive primers".
4461:
3985:
Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; HĂśke, Hartmut (2000). "Amines, Aliphatic".
3769:
3655:
1677:
1329:, although this is rarely employed on an industrial scale. Selectivity is also assured in the
166:
38:
31:
6503:
6406:
6022:
5886:
5774:
3889:
1543:
1338:
691:
45:
6438:
6419:
6217:
6205:
5855:
5300:
4803:
4355:
3814:
3773:
3688:
3388:
3355:
1669:
1472:
4687:
4579:
4570:
3483:, which is one of the primary influences on the three-dimensional structures of proteins.
1419:
is more commonly employed for the reduction of these same groups on the laboratory scale.
1326:
326:
8:
6446:
6411:
6162:
5161:
3348:
3322:
1629:
1587:
1558:
1423:
4838:
4807:
3869:
6454:
6317:
6154:
4551:
3824:
3794:
3761:
3749:
3713:
3307:
2566:
1103:
680:
556:
462:
and have a charged nitrogen center. Quaternary ammonium salts exist with many kinds of
217:
646:, the H-N-H scissor mode appears near 1600 cm, the C-N stretch near 1000 cm, and the R
536:
significantly influences the properties of primary and secondary amines. For example,
6330:
5845:
5815:
5573:
5195:
4916:
4906:
4858:
4819:
4760:
4729:
4667:
4627:
4590:
4543:
4506:
4499:
4479:
4432:
4399:
4364:
4336:
4282:
4253:
4188:
4099:
Hellwich, K.-H.; Hartshorn, R. M.; Yerin, A.; Damhus, T.; Hutton, A. T. (June 2021).
4034:
4000:
3953:
3239:
3220:
3201:
3190:
2452:
1704:
1573:
1531:
1330:
1107:
676:
638:
621:
147:
4555:
3736:
S) from natural gas and refinery process streams. They may also be used to remove CO
3312:
6599:
6378:
6273:
6198:
6070:
5550:
5044:
4982:
4850:
4811:
4752:
4721:
4659:
4619:
4535:
4471:
4391:
4310:
4245:
4217:
4180:
4159:
3992:
3839:
3729:
3701:
3663:
3565:
3417:
3378:
3276:
3155:
1491:
1073:
724:
572:
533:
155:
151:
123:
76:
4421:
4163:
6631:
6561:
6363:
6261:
5769:
5528:
5523:
5506:
5489:
5290:
5039:
4946:
3945:
3765:
3595:
3262:
3257:
2221:
1661:
1520:
1496:
1357:
916:
616:, whereas those with large substituents are lipophilic. Aromatic amines, such as
435:
381:
4359:
6515:
6470:
6462:
6142:
6129:
6107:
6006:
5840:
5835:
5711:
5706:
5701:
5494:
5461:
5245:
5227:
5217:
3834:
3745:
3721:
3709:
3575:
3528:
Primary aromatic amines are used as a starting material for the manufacture of
3507:, or amine, group remains. Amine hormones are synthesized from the amino acids
3425:
3413:
3373:
3281:
3244:
3183:
2948:
1403:
989:
950:
803:
521:
416:
415:âIn tertiary amines, nitrogen has three organic substituents. Examples include
402:
286:
276:
Amines can be classified according to the nature and number of substituents on
257:
225:
209:
205:
4815:
4184:
3602:
are psychostimulant amines that are listed as controlled substances by the US
6625:
6579:
6478:
6341:
6325:
6296:
5985:
5860:
5808:
5739:
5625:
5615:
5610:
5600:
5595:
5545:
5540:
5456:
5451:
5441:
5295:
5250:
5212:
5200:
5171:
5049:
4920:
4862:
4823:
4756:
4733:
4663:
4562:
4395:
3996:
3637:
3615:
3599:
3585:
3569:
3544:
3536:
3337:
3179:
1715:
1673:
1477:
1391:
1383:
779:
668:
406:
398:
4791:
6587:
6532:
6486:
6350:
6174:
6150:
6112:
5791:
5678:
5673:
5650:
5401:
5240:
5166:
5103:
5098:
5076:
5032:
5017:
5007:
4631:
4475:
4257:
3627:
3609:
3250:
2562:
2535:
2319:
1637:
1334:
1111:
643:
560:
504:
4902:
Epoxy Resins, Curing Agents, Compounds, and
Modifiers: An Industrial Guide
4900:
4547:
4483:
6494:
6280:
6229:
6193:
5850:
5803:
5764:
5645:
5533:
5518:
5513:
5501:
5066:
5061:
5027:
5022:
5012:
4990:
4328:
4272:
3819:
3641:
3623:
3591:
3480:
3476:
3444:
3421:
3195:
2217:
1700:
1633:
1591:
881:
755:
537:
373:
350:
291:
185:
57:
4539:
4314:
4221:
3847:
as determined by the
International Union of Pure and Applied Chemistry (
6102:
5759:
5750:
5630:
5585:
5481:
5446:
5436:
5376:
5312:
5235:
5183:
3802:
3790:
3619:
3550:
3508:
3441:
3409:
3360:
3268:
2935:{\displaystyle {\ce {R2NH + R'(R''CH2)C=O -> R''CH=C(NR2)R' + H2O}}}
1371:
1129:
830:
568:
541:
487:
443:
377:
201:
27:
Chemical compounds and groups containing nitrogen with a lone pair (:N)
4854:
4623:
4249:
4175:
J. W. Smith (1968). S. Patai (ed.). "Basicity and complex formation".
3412:
releases amines, famously in the case of decaying fish which smell of
2530:
Aryldiazoniums couple with electron-rich aromatic compounds such as a
1660:
Aside from their basicity, the dominant reactivity of amines is their
544:
amines are gases under standard conditions, whereas the corresponding
6575:
6305:
6248:
6088:
5994:
5726:
5640:
5605:
5590:
5578:
5421:
5396:
5205:
4747:
Eller K, Henkes E, Rossbacher R, HĂśke H (2005). "Amines, Aliphatic".
4725:
3672:
3645:
3581:
3437:
3433:
2782:
Similarly, secondary amines react with ketones and aldehydes to form
2441:
2038:
1530:
Useful for reactions that trap unstable imine intermediates, such as
699:
663:
439:
335:
Amines, alkyl and aryl alike, are organized into three subcategories
162:
66:
4951:
2045:
6583:
6269:
6080:
5964:
5941:
5910:
5734:
5688:
5655:
5351:
5257:
5131:
5086:
5071:
4208:
Hall, H. K. (1957). "Correlation of the Base
Strengths of Amines".
3741:
3676:
3512:
3429:
2944:
2554:
1582:
1128:
Industrially significant alkyl amines are prepared from ammonia by
684:
612:
NH). Small aliphatic amines display significant solubility in many
545:
483:
369:
277:
253:
197:
181:
158:
3760:
Amines are often used as epoxy resin curing agents. These include
6605:
6593:
6569:
6236:
6181:
6124:
6097:
6075:
6065:
5980:
5956:
5696:
5620:
5471:
5466:
5431:
5416:
5411:
5381:
5364:
5188:
5115:
5081:
3680:
3529:
3491:
3460:
3300:
3225:
2956:
2783:
2323:
1595:
1535:
1429:
1387:
854:
617:
613:
549:
479:
388:
361:
346:
221:
213:
170:
4333:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
4278:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
3561:
Most drugs and drug candidates contain amine functional groups:
2430:{\displaystyle {\ce {ANH2 + HNO2 + HX -> AN2+ + X- + 2 H2O}}}
1426:, which can either proceed catalytically or stoichiometrically.
1072:
The degree of solvation of the protonated amine, which includes
517:
500:
5784:
5716:
5560:
5269:
5262:
5156:
5137:
5126:
5110:
5056:
3829:
3684:
3669:
3464:
3342:
3327:
3213:
2952:
2550:
2538:. Such reactions are widely applied to the production of dyes.
2531:
1665:
1655:
1578:
463:
345:
atoms adjacent to the nitrogen (how many hydrogen atoms of the
342:
3124:{\displaystyle {\ce {Hg^2+ + R2NCH2R' <=> Hg + + + H+}}}
200:
atom may be called alkylarylamines). Important amines include
135:
106:
88:
6057:
6052:
6014:
5665:
5635:
5568:
5426:
5391:
5386:
5307:
5274:
5178:
5002:
4270:
4108:
The International Union of Pure and Applied Chemistry (IUPAC)
4033:(3rd ed.). New York, NY: McGraw-Hill. pp. 949â993.
3848:
3173:
2565:(R' = H), these products typically exist as cyclic
2558:
1726:
1681:
1641:
1599:
1548:
1525:
1510:
1482:
This reaction also takes place with a reducing agent such as
1399:
1395:
365:
265:
189:
49:
4098:
6611:
5093:
4526:
Dill, Ken A. (1990). "Dominant forces in protein folding".
2677:{\displaystyle {\ce {RNH2 + R'_2C=O -> R'_2C=NR + H2O}}}
1711:
420:
384:
193:
129:
79:
4234:
1360:, is used industrially to produce tertiary amines such as
727:. Compared to alkali metal hydroxides, amines are weaker.
360:âPrimary amines arise when one of three hydrogen atoms in
4837:
Chen, Fengjun; Liu, Fan; Du, Xiaogang (10 January 2023).
4746:
4584:
4451:
3984:
3468:
3317:
By cleavage (tertiary amines only) with cyanogen bromide
3078:
3006:
2993:
2925:
2897:
2843:
2804:
2754:
2734:
2706:
2667:
2639:
2607:
2587:
2513:
2420:
2363:
2347:
2293:
2280:
2264:
2245:
2184:
2152:
2101:
2083:
1993:
1959:
1941:
1843:
1795:
1777:
1297:
1255:
1191:
1175:
1159:
454:-phenylpiperidine are examples of cyclic tertiary amines.
100:
4653:
3875:
The American Heritage Dictionary of the English Language
1422:
Many amines are produced from aldehydes and ketones via
4385:
3138:
An overview of the reactions of amines is given below:
4790:
Seo, Jiae; Yui, Nobuhiko; Seo, Ji-Hun (January 2019).
4101:"Brief Guide to the Nomenclature of Organic Chemistry"
3038:
2773:{\displaystyle {\ce {R'_2C=NR + H2 -> R'_2CH-NHR}}}
3588:, as amine hydrochlorides, are used as decongestants.
3459:) are the most common positively charged moieties in
2965:
2792:
2690:
2575:
2464:
2335:
2233:
2126:
2090:
2072:
1948:
1930:
1857:
1784:
1766:
1738:
1225:
1141:
138:
109:
91:
2549:
is an important reaction. Primary amines react with
1311:{\displaystyle {\ce {RX + 2 R'NH2 -> RR'NH + X}}}
268:
and have different chemical properties from amines.
3408:Amines are ubiquitous in biology. The breakdown of
336:
132:
126:
103:
97:
85:
82:
4498:
4420:
3332:Proceeds by β-elimination of less hindered carbon
3123:
2934:
2772:
2684:Reduction of these imines gives secondary amines:
2676:
2519:
2429:
2302:
2205:
1310:
1201:{\displaystyle {\ce {ROH + NH3 -> RNH2 + H2O}}}
1200:
3720:(MDEA) are widely used industrially for removing
3046:
3045:
3028:
3027:
2114:
2113:
1810:
1809:
1808:
1807:
1753:
1752:
1707:, is a chemical test for the presence of amines.
298:
6623:
4354:
3662:are key basic structures for a large variety of
2303:{\displaystyle {\ce {R2NH + SO3 -> R2NSO3H}}}
1699:Similarly, with sulfonyl chlorides, one obtains
1680:react with primary and secondary amines to form
4130:"Organic Nitrogen Compounds II: Primary Amines"
2520:{\displaystyle {\ce {AN2+ + Y- -> AY + N2}}}
627:
4749:Ullmann's Encyclopedia of Industrial Chemistry
4656:Ullmann's Encyclopedia of Industrial Chemistry
4609:
4388:Ullmann's Encyclopedia of Industrial Chemistry
4281:(6th ed.), New York: Wiley-Interscience,
4020:
4018:
4016:
3988:Ullmann's Encyclopedia of Industrial Chemistry
1211:
372:group. Important primary alkyl amines include
5926:
4967:
2440:Anilines and naphthylamines form more stable
419:, which has a distinctively fishy smell, and
4505:(3rd ed.). New York: Worth Publishing.
4327:
4300:
3789:Low molecular weight simple amines, such as
3755:
2131:
1862:
1656:Alkylation, acylation, and sulfonation, etc.
37:"Amino" redirects here. For other uses, see
4688:"amine curing agent: Topics by Science.gov"
4174:
4013:
3397:are used. Thiocyanate smells like mustard.
271:
5933:
5919:
4974:
4960:
1710:Because amines are basic, they neutralize
4836:
4789:
4496:
4465:
3980:
3978:
3976:
3974:
3972:
3970:
3968:
3271:salts, with primary and secondary amines
2409:
1672:. Amines are alkylated by alkyl halides.
1236:
4589:. Houston: OpenStax CNX. 17.2 Hormones.
4418:
4210:Journal of the American Chemical Society
3920:"amine â definition of amine in English"
3868:
3744:and may have potential for abatement of
3518:
2326:("phenylamine") (A = aryl or naphthyl):
690:Amines of the type NHRR' and NRRâ˛Râł are
662:
516:
499:
387:, while primary aromatic amines include
56:
4711:
3944:
3021:
2541:
493:Lower amines are named with the suffix
290:have the nitrogen atom connected to an
284:contain only H and alkyl substituents.
14:
6624:
4905:. Park Ridge, NJ: Noyes Publications.
4177:Patai's Chemistry of Functional Groups
3965:
3403:
1450:
528:
5914:
4981:
4955:
4898:
4501:Lehninger, Principles of Biochemistry
4419:Williams, D. L. H. (1988).
4127:
4024:
3922:. Oxford Dictionaries. Archived from
3900:from the original on 23 February 2015
3779:2,4,6-Tris(dimethylaminomethyl)phenol
1080:
469:
5940:
4881:"Amines | Introduction to Chemistry"
4525:
4207:
3952:(3rd ed.), Belmont: Wadsworth,
1703:. This transformation, known as the
1325:Selectivity can be improved via the
1089:
683:of the stereocenter is about 7
1377:
1065:The basicity of amines depends on:
24:
4873:
4843:Journal of Applied Polymer Science
4497:Nelson, D. L.; Cox, M. M. (2000).
2455:gives the corresponding nitriles:
2125:
2089:
2066:
2018:
1947:
1924:
1856:
1783:
1760:
1690:
1102:In aprotic polar solvents such as
709:
25:
6648:
4928:
4335:(4th ed.), New York: Wiley,
4070:"3.11 Basic properties of amines"
3748:. Related processes are known as
3486:
3463:, specifically in the amino acid
3163:Degree of substitution increases
620:, have their lone pair electrons
4574: This article incorporates
4569:
4238:The Journal of Organic Chemistry
4080:from the original on 23 May 2021
4025:Smith, Janice Gorzynski (2011).
3845:Official naming rules for amines
3695:
2451:group with anions. For example,
2313:
1568:Upon treatment with strong base
1123:
571:of simple amines is enhanced by
325:
318:
311:
224:are also called amines, such as
122:
75:
4830:
4783:
4773:
4740:
4705:
4680:
4647:
4638:
4603:
4519:
4490:
4445:
4412:
4379:
4348:
4321:
4294:
4264:
4228:
4201:
4168:
4152:
3479:groups of other amino acids in
1664:. Most primary amines are good
1351:
658:
4714:Pigment & Resin Technology
4612:Journal of Medicinal Chemistry
4121:
4092:
4062:
3938:
3912:
3890:"Amine definition and meaning"
3882:
3878:(5th ed.). HarperCollins.
3862:
3097:
3065:
3048:
3023:
2900:
2884:
2861:
2846:
2822:
2737:
2622:
2494:
2372:
2267:
2106:
2068:
1964:
1926:
1800:
1762:
1300:
1276:
1258:
1162:
510:Higher amines have the prefix
184:atoms have been replaced by a
13:
1:
4360:"β-Naphthylmercuric chloride"
4164:10.1002/9780470682531.pat0385
3855:
3793:, are only weakly toxic with
3295:HofmannâMartius rearrangement
555:The nitrogen atom features a
4796:Chemical Engineering Journal
4454:Journal of Molecular Biology
4303:Journal of Organic Chemistry
3370:Hoffmann's mustard oil test
1650:
1515:Synthesis of allylic amines
1118:
1028:4-Trifluoromethylaniline (CF
653:
628:Spectroscopic identification
260:, thus having the structure
7:
4136:. Spectroscopy-03-01-2019.
4128:Smith, Brian (March 2019).
3808:
3288:quaternary ammonium cations
3209:Amineâcarbonyl condensation
3133:
1506:Aza-BaylisâHillman reaction
1212:From alkyl and aryl halides
718:
608:) > tertiary ammonium (R
587:) > secondary ammonium (
559:that can bind H to form an
460:quaternary ammonium cations
10:
6653:
4374:, vol. 2, p. 432
3894:Collins English Dictionary
3740:from combustion gases and
3372:
3369:
3359:
3354:
3341:
3336:
3326:
3321:
3311:
3306:
3298:
3293:
3280:
3275:
3256:
3243:
3238:
3224:
3219:
3212:
3207:
3194:
3189:
3172:
3167:
3159:
3154:
1714:to form the corresponding
1625:
1622:EschweilerâClarke reaction
1620:
1611:
1606:
1577:
1572:
1562:
1557:
1547:
1542:
1524:
1519:
1509:
1504:
1495:
1490:
1471:
1076:by the groups on nitrogen.
442:and the six-membered ring
245:is called an amino group.
43:
36:
29:
6560:
6399:
6141:
6037:
5949:
5869:
5828:
5748:
5725:
5687:
5664:
5559:
5480:
5350:
5327:
5283:
5226:
5149:
5124:
4989:
4940:Factsheet, amines in food
4899:Flick, Ernest W. (1993).
4885:courses.lumenlearning.com
4816:10.1016/j.cej.2018.09.020
4185:10.1002/9780470771082.ch4
3784:
3756:Epoxy resin curing agents
3650:tricyclic antidepressants
3632:tricyclic antidepressants
3169:SchottenâBaumann reaction
1686:SchottenâBaumann reaction
1484:lithium aluminium hydride
1346:Buchwald-Hartwig reaction
723:Like ammonia, amines are
704:quaternary ammonium salts
401:, while an example of an
349:molecule are replaced by
4945:19 February 2018 at the
4757:10.1002/14356007.a02_001
4664:10.1002/14356007.a17_073
4587:Anatomy & Physiology
4396:10.1002/14356007.a03_245
3997:10.1002/14356007.a02_001
3556:
2947:ions reversibly oxidize
1608:HofmannâLĂśffler reaction
1564:Quaternary ammonium salt
642:modes. For the case of
272:Classification of amines
44:Not to be confused with
5880:chemical classification
4751:. Weinheim: Wiley-VCH.
3991:. Weinheim: Wiley-VCH.
3656:Substituted tryptamines
3523:
3233:peroxymonosulfuric acid
1668:for metal ions to give
341:based on the number of
180:), wherein one or more
165:. Formally, amines are
4476:10.1006/jmbi.1997.1498
3770:tetraethylenepentamine
3467:. The anionic polymer
3420:are amines, including
3125:
2936:
2774:
2678:
2521:
2431:
2304:
2207:
2052:
1696:
1670:coordination complexes
1312:
1202:
733:Alkylamine or aniline
672:
650:N-H bend near 810 cm.
525:
507:
450:-methylpiperidine and
62:
39:Amino (disambiguation)
32:Amine (disambiguation)
5887:chemical nomenclature
4076:. 28 September 2015.
3519:Application of amines
3126:
2937:
2775:
2679:
2522:
2432:
2305:
2224:or sources thereof:
2208:
2034:
1694:
1339:potassium phthalimide
1313:
1203:
671:on the nitrogen atom.
666:
520:
503:
395:Secondary (2°) amines
60:
4578:available under the
4429:Cambridge University
4074:Chemistry LibreTexts
3815:Acid-base extraction
3774:triethylenetetramine
3718:methyldiethanolamine
3634:and tertiary amines.
3389:mercury(II) chloride
3365:Primary amines only
3356:Carbylamine reaction
2963:
2790:
2688:
2573:
2542:Conversion to imines
2462:
2333:
2231:
2220:upon treatment with
2021:substituted-ammonium
1736:
1473:Staudinger reduction
1223:
1139:
413:Tertiary (3°) amines
306:Tertiary (3°) amine
303:Secondary (2°) amine
30:For other uses, see
5343:not C, H or O)
4935:Synthesis of amines
4808:2019ChEnJ.356..303S
4540:10.1021/bi00483a001
4315:10.1021/jo00376a053
4271:Smith, Michael B.;
4222:10.1021/ja01577a030
4027:"Chapter 25 Amines"
3926:on 23 February 2015
3404:Biological activity
3349:Hofmann elimination
3323:Hofmann elimination
3080:
3034:
3008:
2995:
2927:
2899:
2845:
2806:
2757:
2736:
2709:
2669:
2642:
2610:
2589:
2515:
2480:
2422:
2389:
2365:
2349:
2318:Amines reacts with
2295:
2282:
2266:
2247:
2186:
2154:
2103:
2085:
2051:
2044:
1995:
1961:
1943:
1845:
1797:
1779:
1630:Reductive amination
1588:Reductive amination
1559:Hofmann elimination
1544:Hofmann degradation
1451:Specialized methods
1424:reductive amination
1382:Via the process of
1299:
1257:
1193:
1177:
1161:
529:Physical properties
358:Primary (1°) amines
256:atom attached to a
5785:Hypervalent iodine
3825:Amine gas treating
3762:dimethylethylamine
3714:diisopropanolamine
3308:von Braun reaction
3202:sulfonyl chlorides
3121:
3068:
3053:
2996:
2983:
2932:
2915:
2887:
2833:
2794:
2770:
2740:
2724:
2692:
2674:
2657:
2625:
2593:
2577:
2517:
2503:
2466:
2427:
2410:
2375:
2353:
2337:
2300:
2283:
2270:
2254:
2235:
2203:
2201:
2194:
2174:
2166:
2159:
2142:
2130:
2104:
2091:
2088:
2086:
2073:
2031:
2015:
1983:
1962:
1949:
1946:
1944:
1931:
1887:
1880:
1861:
1833:
1825:
1818:
1798:
1785:
1782:
1780:
1767:
1697:
1532:Grignard reactions
1308:
1287:
1245:
1198:
1181:
1165:
1149:
1081:Electronic effects
681:nitrogen inversion
673:
557:lone electron pair
526:
524:(or butan-2-amine)
508:
470:Naming conventions
364:is replaced by an
300:Primary (1°) amine
63:
6637:Functional groups
6619:
6618:
5908:
5907:
5846:Sulfenyl chloride
5824:
5823:
5323:
5322:
5142:(only C, H and O)
4983:Functional groups
4912:978-0-8155-1708-5
4855:10.1002/app.53302
4624:10.1021/jm200187y
4618:(10): 3451â3479.
4596:978-1-947172-04-3
4427:. Cambridge, UK:
4372:Collected Volumes
4365:Organic Syntheses
4309:(26): 5338â5341.
4288:978-0-471-72091-1
4250:10.1021/jo048252w
4216:(20): 5441â5444.
4040:978-0-07-337562-5
4031:Organic chemistry
3950:Organic Chemistry
3664:psychedelic drugs
3418:neurotransmitters
3401:
3400:
3313:Organic cyanamide
3299:Aryl-substituted
3240:Organic oxidation
3221:Organic oxidation
3191:Hinsberg reaction
3113:
3092:
3083:
3071:
3059:
3055:
3012:
2999:
2986:
2970:
2930:
2918:
2907:
2890:
2882:
2874:
2867:
2860:
2852:
2836:
2828:
2816:
2809:
2797:
2768:
2760:
2743:
2727:
2720:
2712:
2695:
2672:
2660:
2653:
2645:
2628:
2621:
2613:
2596:
2580:
2561:. In the case of
2506:
2499:
2487:
2469:
2425:
2413:
2396:
2378:
2371:
2356:
2340:
2298:
2286:
2273:
2257:
2250:
2238:
2199:
2189:
2177:
2172:
2170:
2164:
2145:
2135:
2134:
2129:
2124:
2111:
2110:
2094:
2087:
2076:
2065:
2062:
2058:
2056:
2049:
2042:
2029:
2027:
2022:
2004:
1986:
1978:
1969:
1968:
1952:
1945:
1934:
1917:
1913:
1905:
1900:
1898:
1897:
1885:
1875:
1866:
1865:
1860:
1855:
1836:
1831:
1829:
1823:
1805:
1804:
1788:
1781:
1770:
1759:
1756:
1746:
1742:
1740:
1705:Hinsberg reaction
1648:
1647:
1574:Leuckart reaction
1333:, which involves
1331:Gabriel synthesis
1327:DelĂŠpine reaction
1306:
1290:
1282:
1271:
1264:
1248:
1240:
1229:
1196:
1184:
1168:
1152:
1145:
1090:Solvation effects
1063:
1062:
742:protonated amine
706:are resolvable).
639:infrared spectrum
339:
333:
332:
252:Compounds with a
152:functional groups
16:(Redirected from
6644:
6609:
6597:
6573:
6562:Oxidation states
6391:
6390:
6359:
6358:
6293:
6292:
6257:
6256:
6245:
6244:
6190:
6189:
5935:
5928:
5921:
5912:
5911:
5875:
5780:Trifluoromethoxy
5348:
5347:
5344:
5147:
5146:
5143:
4996:
4976:
4969:
4962:
4953:
4952:
4924:
4895:
4893:
4891:
4867:
4866:
4834:
4828:
4827:
4787:
4781:
4777:
4771:
4770:
4744:
4738:
4737:
4726:10.1108/eb043156
4709:
4703:
4702:
4700:
4698:
4684:
4678:
4677:
4651:
4645:
4642:
4636:
4635:
4607:
4601:
4600:
4573:
4566:
4560:
4559:
4523:
4517:
4516:
4504:
4494:
4488:
4487:
4469:
4449:
4443:
4442:
4426:
4416:
4410:
4409:
4383:
4377:
4375:
4368:
4356:A. N. Nesmajanow
4352:
4346:
4345:
4325:
4319:
4318:
4298:
4292:
4291:
4268:
4262:
4261:
4244:(3): 1019â1028.
4232:
4226:
4225:
4205:
4199:
4198:
4172:
4166:
4156:
4150:
4149:
4147:
4145:
4125:
4119:
4118:
4116:
4114:
4105:
4096:
4090:
4089:
4087:
4085:
4066:
4060:
4059:
4057:
4055:
4049:
4043:. Archived from
4022:
4011:
4010:
3982:
3963:
3962:
3946:McMurry, John E.
3942:
3936:
3935:
3933:
3931:
3916:
3910:
3909:
3907:
3905:
3886:
3880:
3879:
3866:
3840:Ligand isomerism
3746:greenhouse gases
3730:hydrogen sulfide
3702:monoethanolamine
3566:Chlorpheniramine
3541:Direct brown 138
3506:
3505:
3504:
3458:
3457:
3456:
3396:
3386:
3379:Carbon disulfide
3277:Emde degradation
3156:Amine alkylation
3147:Reaction product
3141:
3140:
3130:
3128:
3127:
3122:
3120:
3119:
3118:
3111:
3106:
3105:
3100:
3096:
3090:
3088:
3081:
3079:
3076:
3069:
3057:
3056:
3054:
3052:
3051:
3044:
3036:
3035:
3033:
3026:
3018:
3016:
3010:
3007:
3004:
2997:
2994:
2991:
2984:
2979:
2978:
2968:
2941:
2939:
2938:
2933:
2931:
2928:
2926:
2923:
2916:
2911:
2905:
2903:
2898:
2895:
2888:
2880:
2879:
2872:
2871:
2865:
2858:
2857:
2850:
2849:
2844:
2841:
2834:
2832:
2826:
2820:
2814:
2807:
2805:
2802:
2795:
2779:
2777:
2776:
2771:
2769:
2766:
2765:
2758:
2756:
2755:
2748:
2741:
2735:
2732:
2725:
2718:
2717:
2710:
2708:
2707:
2700:
2693:
2683:
2681:
2680:
2675:
2673:
2670:
2668:
2665:
2658:
2651:
2650:
2643:
2641:
2640:
2633:
2626:
2619:
2618:
2611:
2609:
2608:
2601:
2594:
2588:
2585:
2578:
2526:
2524:
2523:
2518:
2516:
2514:
2511:
2504:
2497:
2493:
2492:
2485:
2479:
2474:
2467:
2450:
2436:
2434:
2433:
2428:
2426:
2423:
2421:
2418:
2411:
2402:
2401:
2394:
2388:
2383:
2376:
2369:
2364:
2361:
2354:
2348:
2345:
2338:
2309:
2307:
2306:
2301:
2299:
2296:
2294:
2291:
2284:
2281:
2278:
2271:
2265:
2262:
2255:
2248:
2246:
2243:
2236:
2212:
2210:
2209:
2204:
2202:
2200:
2197:
2195:
2190:
2187:
2185:
2182:
2175:
2165:
2162:
2160:
2155:
2153:
2150:
2143:
2141:
2136:
2127:
2122:
2121:
2119:
2112:
2109:
2102:
2099:
2092:
2084:
2081:
2074:
2071:
2063:
2061:
2054:
2053:
2050:
2047:
2043:
2040:
2030:
2028:
2026:carboxylate salt
2025:
2023:
2020:
2016:
2011:
2010:
2009:
2002:
2000:
1994:
1991:
1984:
1979:
1976:
1975:
1970:
1967:
1960:
1957:
1950:
1942:
1939:
1932:
1929:
1923:
1922:
1915:
1912:
1910:
1903:
1895:
1894:
1886:
1883:
1881:
1876:
1873:
1872:
1867:
1858:
1853:
1852:
1850:
1844:
1841:
1834:
1824:
1821:
1819:
1814:
1806:
1803:
1796:
1793:
1786:
1778:
1775:
1768:
1765:
1757:
1755:
1751:
1744:
1724:
1492:Schmidt reaction
1458:
1457:
1446:
1417:
1409:
1378:Reductive routes
1317:
1315:
1314:
1309:
1307:
1304:
1303:
1298:
1295:
1288:
1286:
1280:
1269:
1268:
1262:
1256:
1253:
1246:
1244:
1238:
1227:
1207:
1205:
1204:
1199:
1197:
1194:
1192:
1189:
1182:
1176:
1173:
1166:
1160:
1157:
1150:
1143:
1074:steric hindrance
1059:
1057:
1049:
1023:
1021:
1013:
984:
982:
974:
945:
943:
935:
924:-Dimethylaniline
911:
909:
901:
882:4-Methoxyaniline
876:
874:
866:
849:
847:
825:
823:
815:
798:
796:
774:
772:
730:
729:
607:
606:
605:
597:
596:
586:
585:
584:
573:hydrogen bonding
534:Hydrogen bonding
337:
329:
322:
315:
297:
296:
282:Aliphatic amines
263:
244:
238:The substituent
234:
179:
145:
144:
141:
140:
137:
134:
131:
128:
120:
116:
115:
112:
111:
108:
105:
102:
99:
94:
93:
90:
87:
84:
81:
21:
6652:
6651:
6647:
6646:
6645:
6643:
6642:
6641:
6622:
6621:
6620:
6615:
6603:
6591:
6567:
6556:
6552:
6544:
6536:
6528:
6519:
6511:
6507:
6498:
6490:
6482:
6474:
6466:
6458:
6450:
6442:
6432:
6423:
6415:
6395:
6389:
6386:
6385:
6384:
6382:
6375:
6371:
6367:
6357:
6354:
6353:
6352:
6345:
6338:
6334:
6321:
6313:
6309:
6300:
6291:
6288:
6287:
6286:
6284:
6277:
6265:
6255:
6252:
6251:
6250:
6243:
6240:
6239:
6238:
6233:
6225:
6221:
6213:
6209:
6202:
6188:
6185:
6184:
6183:
6178:
6170:
6166:
6158:
6137:
6133:
6120:
6116:
6092:
6084:
6061:
6048:
6033:
6027:
6018:
6010:
6002:
5998:
5989:
5976:
5968:
5960:
5945:
5939:
5909:
5904:
5873:
5865:
5820:
5775:Trichloromethyl
5770:Trifluoromethyl
5744:
5721:
5683:
5660:
5555:
5524:Phosphine oxide
5476:
5342:
5340:
5339:
5337:
5335:
5333:
5331:
5329:
5319:
5279:
5222:
5141:
5140:
5135:
5130:
5120:
4994:
4993:
4985:
4980:
4947:Wayback Machine
4931:
4913:
4889:
4887:
4879:
4876:
4874:Further reading
4871:
4870:
4835:
4831:
4788:
4784:
4778:
4774:
4767:
4745:
4741:
4710:
4706:
4696:
4694:
4686:
4685:
4681:
4674:
4652:
4648:
4643:
4639:
4608:
4604:
4597:
4567:
4563:
4534:(31): 7133â55.
4524:
4520:
4513:
4495:
4491:
4450:
4446:
4439:
4431:. p. 195.
4417:
4413:
4406:
4384:
4380:
4370:
4353:
4349:
4343:
4326:
4322:
4299:
4295:
4289:
4269:
4265:
4233:
4229:
4206:
4202:
4195:
4173:
4169:
4157:
4153:
4143:
4141:
4126:
4122:
4112:
4110:
4103:
4097:
4093:
4083:
4081:
4068:
4067:
4063:
4053:
4051:
4050:on 28 June 2018
4047:
4041:
4023:
4014:
4007:
3983:
3966:
3960:
3943:
3939:
3929:
3927:
3918:
3917:
3913:
3903:
3901:
3888:
3887:
3883:
3867:
3863:
3858:
3811:
3798:
3787:
3766:cyclohexylamine
3758:
3739:
3735:
3727:
3698:
3660:phenethylamines
3596:methamphetamine
3559:
3526:
3521:
3503:
3500:
3499:
3498:
3496:
3489:
3455:
3452:
3451:
3450:
3448:
3406:
3395:
3391:
3385:
3381:
3263:Zincke aldehyde
3258:Zincke reaction
3184:acid anhydrides
3136:
3114:
3110:
3101:
3089:
3084:
3077:
3072:
3064:
3063:
3047:
3040:
3039:
3037:
3029:
3022:
3020:
3019:
3017:
3009:
3005:
3000:
2992:
2987:
2971:
2967:
2966:
2964:
2961:
2960:
2949:tertiary amines
2924:
2919:
2904:
2896:
2891:
2883:
2875:
2864:
2853:
2842:
2837:
2825:
2821:
2813:
2803:
2798:
2793:
2791:
2788:
2787:
2761:
2753:
2749:
2744:
2733:
2728:
2713:
2705:
2701:
2696:
2691:
2689:
2686:
2685:
2666:
2661:
2646:
2638:
2634:
2629:
2614:
2606:
2602:
2597:
2586:
2581:
2576:
2574:
2571:
2570:
2547:Imine formation
2544:
2512:
2507:
2488:
2484:
2475:
2470:
2465:
2463:
2460:
2459:
2453:cuprous cyanide
2449:
2445:
2419:
2414:
2397:
2393:
2384:
2379:
2362:
2357:
2346:
2341:
2336:
2334:
2331:
2330:
2316:
2292:
2287:
2279:
2274:
2263:
2258:
2244:
2239:
2234:
2232:
2229:
2228:
2222:sulfur trioxide
2216:Amines undergo
2196:
2183:
2178:
2173:
2171:
2161:
2151:
2146:
2137:
2120:
2115:
2105:
2100:
2095:
2082:
2077:
2067:
2060:
2059:
2057:
2055:
2046:
2039:
2033:
2032:
2024:
2019:
2017:
2005:
2001:
1996:
1992:
1987:
1971:
1963:
1958:
1953:
1940:
1935:
1925:
1918:
1914:
1911:
1906:
1902:
1901:
1899:
1884:carboxylic acid
1882:
1868:
1851:
1846:
1842:
1837:
1832:
1830:
1820:
1799:
1794:
1789:
1776:
1771:
1761:
1754:
1747:
1743:
1741:
1739:
1737:
1734:
1733:
1722:
1718:
1695:Amide formation
1678:acid anhydrides
1662:nucleophilicity
1658:
1653:
1521:Birch reduction
1497:Carboxylic acid
1453:
1445:
1441:
1437:
1433:
1416:
1412:
1407:
1380:
1358:Ritter reaction
1354:
1296:
1291:
1279:
1275:
1261:
1254:
1249:
1237:
1226:
1224:
1221:
1220:
1214:
1190:
1185:
1174:
1169:
1158:
1153:
1142:
1140:
1137:
1136:
1132:with alcohols:
1126:
1121:
1098:
1092:
1083:
1055:
1053:
1047:
1043:
1039:
1035:
1031:
1019:
1017:
1011:
1007:
1003:
999:
995:
980:
978:
972:
968:
964:
960:
956:
941:
939:
933:
929:
907:
905:
899:
895:
891:
887:
872:
870:
864:
860:
845:
843:
836:
821:
819:
813:
809:
794:
792:
785:
770:
768:
761:
750:
741:
739:
721:
712:
710:Aromatic amines
661:
656:
649:
636:
630:
611:
604:
601:
600:
599:
595:
592:
591:
590:
588:
583:
580:
579:
578:
576:
566:
531:
472:
382:buffering agent
287:Aromatic amines
274:
261:
243:
239:
233:
229:
220:derivatives of
206:biogenic amines
178:
174:
154:that contain a
125:
121:
118:
96:
78:
74:
53:
42:
35:
28:
23:
22:
15:
12:
11:
5:
6650:
6640:
6639:
6634:
6617:
6616:
6566:
6564:
6558:
6557:
6555:
6554:
6550:
6546:
6542:
6538:
6534:
6530:
6526:
6522:
6517:
6513:
6509:
6505:
6501:
6496:
6492:
6488:
6484:
6480:
6476:
6472:
6468:
6464:
6460:
6456:
6452:
6448:
6444:
6440:
6436:
6430:
6425:
6421:
6417:
6413:
6409:
6403:
6401:
6397:
6396:
6394:
6393:
6387:
6380:
6373:
6369:
6365:
6361:
6355:
6348:
6343:
6336:
6332:
6328:
6319:
6315:
6311:
6307:
6303:
6298:
6289:
6282:
6275:
6267:
6263:
6259:
6253:
6241:
6231:
6227:
6223:
6219:
6215:
6211:
6207:
6200:
6196:
6186:
6176:
6172:
6168:
6164:
6160:
6156:
6147:
6145:
6139:
6138:
6136:
6135:
6131:
6127:
6122:
6118:
6114:
6110:
6105:
6100:
6095:
6090:
6086:
6082:
6078:
6073:
6068:
6063:
6059:
6055:
6050:
6046:
6041:
6039:
6035:
6034:
6032:
6031:
6025:
6020:
6016:
6012:
6008:
6004:
6000:
5996:
5992:
5987:
5983:
5978:
5974:
5970:
5966:
5962:
5958:
5953:
5951:
5947:
5946:
5938:
5937:
5930:
5923:
5915:
5906:
5905:
5903:
5902:
5901:
5900:
5895:
5883:
5876:
5870:
5867:
5866:
5864:
5863:
5861:Sulfinylamines
5858:
5853:
5848:
5843:
5841:Phosphoramides
5838:
5836:Isothiocyanate
5832:
5830:
5826:
5825:
5822:
5821:
5819:
5818:
5813:
5812:
5811:
5801:
5800:
5799:
5789:
5788:
5787:
5782:
5777:
5772:
5767:
5756:
5754:
5746:
5745:
5743:
5742:
5737:
5731:
5729:
5723:
5722:
5720:
5719:
5714:
5712:Selenenic acid
5709:
5707:Seleninic acid
5704:
5702:Selenonic acid
5699:
5693:
5691:
5685:
5684:
5682:
5681:
5676:
5670:
5668:
5662:
5661:
5659:
5658:
5653:
5648:
5643:
5638:
5633:
5628:
5623:
5618:
5613:
5608:
5603:
5598:
5593:
5588:
5583:
5582:
5581:
5571:
5565:
5563:
5557:
5556:
5554:
5553:
5548:
5543:
5538:
5537:
5536:
5526:
5521:
5516:
5511:
5510:
5509:
5499:
5498:
5497:
5495:Phosphodiester
5486:
5484:
5478:
5477:
5475:
5474:
5469:
5464:
5459:
5454:
5449:
5444:
5439:
5434:
5429:
5424:
5419:
5414:
5409:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5373:
5372:
5367:
5356:
5354:
5345:
5341:(one element,
5325:
5324:
5321:
5320:
5318:
5317:
5316:
5315:
5305:
5304:
5303:
5298:
5287:
5285:
5281:
5280:
5278:
5277:
5272:
5267:
5266:
5265:
5255:
5254:
5253:
5248:
5243:
5232:
5230:
5224:
5223:
5221:
5220:
5218:Methylenedioxy
5215:
5210:
5209:
5208:
5203:
5193:
5192:
5191:
5186:
5176:
5175:
5174:
5164:
5159:
5153:
5151:
5144:
5122:
5121:
5119:
5118:
5113:
5108:
5107:
5106:
5101:
5091:
5090:
5089:
5084:
5079:
5074:
5069:
5064:
5054:
5053:
5052:
5047:
5037:
5036:
5035:
5030:
5025:
5020:
5015:
5010:
4999:
4997:
4995:(only C and H)
4987:
4986:
4979:
4978:
4971:
4964:
4956:
4950:
4949:
4937:
4930:
4929:External links
4927:
4926:
4925:
4911:
4896:
4875:
4872:
4869:
4868:
4829:
4782:
4772:
4765:
4739:
4704:
4679:
4672:
4646:
4637:
4602:
4595:
4561:
4518:
4511:
4489:
4467:10.1.1.32.3499
4444:
4437:
4411:
4404:
4378:
4347:
4341:
4320:
4293:
4287:
4263:
4227:
4200:
4193:
4167:
4151:
4120:
4091:
4061:
4039:
4012:
4005:
3964:
3958:
3937:
3911:
3881:
3860:
3859:
3857:
3854:
3853:
3852:
3842:
3837:
3835:Biogenic amine
3832:
3827:
3822:
3817:
3810:
3807:
3796:
3786:
3783:
3757:
3754:
3737:
3733:
3725:
3722:carbon dioxide
3710:diethanolamine
3697:
3694:
3693:
3692:
3667:
3653:
3635:
3613:
3607:
3589:
3579:
3576:Chlorpromazine
3573:
3558:
3555:
3554:
3553:
3548:
3542:
3539:
3525:
3522:
3520:
3517:
3501:
3488:
3487:Amine hormones
3485:
3453:
3426:norepinephrine
3414:trimethylamine
3405:
3402:
3399:
3398:
3393:
3383:
3376:
3374:Isothiocyanate
3371:
3367:
3366:
3363:
3358:
3352:
3351:
3345:
3340:
3334:
3333:
3330:
3325:
3319:
3318:
3315:
3310:
3304:
3303:
3297:
3291:
3290:
3284:
3282:Tertiary amine
3279:
3273:
3272:
3265:
3260:
3254:
3253:
3247:
3245:Diazonium salt
3242:
3236:
3235:
3229:
3223:
3217:
3216:
3211:
3205:
3204:
3198:
3193:
3187:
3186:
3180:acyl chlorides
3176:
3171:
3165:
3164:
3161:
3158:
3152:
3151:
3148:
3145:
3135:
3132:
3117:
3109:
3104:
3099:
3095:
3087:
3075:
3067:
3062:
3050:
3043:
3032:
3025:
3015:
3003:
2990:
2982:
2977:
2974:
2922:
2914:
2910:
2902:
2894:
2886:
2878:
2870:
2863:
2856:
2848:
2840:
2831:
2824:
2819:
2812:
2801:
2764:
2752:
2747:
2739:
2731:
2723:
2716:
2704:
2699:
2664:
2656:
2649:
2637:
2632:
2624:
2617:
2605:
2600:
2592:
2584:
2543:
2540:
2528:
2527:
2510:
2502:
2496:
2491:
2483:
2478:
2473:
2447:
2438:
2437:
2417:
2408:
2405:
2400:
2392:
2387:
2382:
2374:
2368:
2360:
2352:
2344:
2315:
2312:
2311:
2310:
2290:
2277:
2269:
2261:
2253:
2242:
2214:
2213:
2193:
2181:
2169:
2158:
2149:
2140:
2133:
2118:
2108:
2098:
2080:
2070:
2037:
2014:
2008:
1999:
1990:
1982:
1974:
1966:
1956:
1938:
1928:
1921:
1909:
1893:
1890:
1879:
1871:
1864:
1849:
1840:
1828:
1817:
1813:
1802:
1792:
1774:
1764:
1750:
1720:
1716:ammonium salts
1674:Acyl chlorides
1657:
1654:
1652:
1649:
1646:
1645:
1627:
1624:
1618:
1617:
1615:
1610:
1604:
1603:
1585:
1576:
1570:
1569:
1566:
1561:
1555:
1554:
1551:
1546:
1540:
1539:
1528:
1523:
1517:
1516:
1513:
1508:
1502:
1501:
1499:
1494:
1488:
1487:
1480:
1475:
1469:
1468:
1465:
1462:
1452:
1449:
1443:
1439:
1435:
1414:
1402:, amides, and
1379:
1376:
1353:
1350:
1337:reacting with
1319:
1318:
1302:
1294:
1285:
1278:
1274:
1267:
1260:
1252:
1243:
1235:
1232:
1213:
1210:
1209:
1208:
1188:
1180:
1172:
1164:
1156:
1148:
1125:
1122:
1120:
1117:
1096:
1091:
1088:
1082:
1079:
1078:
1077:
1070:
1061:
1060:
1051:
1045:
1041:
1037:
1033:
1029:
1025:
1024:
1015:
1009:
1005:
1001:
997:
993:
990:4-Nitroaniline
986:
985:
976:
970:
966:
962:
958:
954:
951:3-Nitroaniline
947:
946:
937:
931:
927:
913:
912:
903:
897:
893:
889:
885:
878:
877:
868:
862:
858:
851:
850:
841:
838:
834:
827:
826:
817:
811:
807:
804:Trimethylamine
800:
799:
790:
787:
783:
776:
775:
766:
763:
759:
752:
751:
748:
743:
737:
734:
720:
717:
711:
708:
677:energy barrier
660:
657:
655:
652:
647:
634:
629:
626:
609:
602:
593:
581:
564:
530:
527:
490:and so forth.
471:
468:
456:
455:
425:
424:
417:trimethylamine
410:
403:aromatic amine
392:
331:
330:
323:
316:
308:
307:
304:
301:
273:
270:
258:carbonyl group
241:
231:
226:monochloramine
210:trimethylamine
176:
26:
18:Tertiary amine
9:
6:
4:
3:
2:
6649:
6638:
6635:
6633:
6630:
6629:
6627:
6613:
6608:
6607:
6601:
6596:
6595:
6589:
6585:
6581:
6577:
6572:
6571:
6565:
6563:
6559:
6553:
6547:
6545:
6539:
6537:
6531:
6529:
6523:
6521:
6514:
6512:
6502:
6500:
6493:
6491:
6485:
6483:
6477:
6475:
6469:
6467:
6461:
6459:
6453:
6451:
6445:
6443:
6437:
6434:
6433:
6426:
6424:
6418:
6416:
6410:
6408:
6405:
6404:
6402:
6398:
6392:
6376:
6362:
6360:
6349:
6347:
6339:
6329:
6327:
6323:
6316:
6314:
6304:
6302:
6294:
6278:
6271:
6268:
6266:
6260:
6258:
6246:
6234:
6228:
6226:
6216:
6214:
6203:
6197:
6195:
6191:
6179:
6173:
6171:
6161:
6159:
6152:
6149:
6148:
6146:
6144:
6140:
6134:
6128:
6126:
6123:
6121:
6111:
6109:
6106:
6104:
6101:
6099:
6096:
6094:
6087:
6085:
6079:
6077:
6074:
6072:
6069:
6067:
6064:
6062:
6056:
6054:
6051:
6049:
6043:
6042:
6040:
6036:
6029:
6028:
6021:
6019:
6013:
6011:
6005:
6003:
5993:
5991:
5984:
5982:
5979:
5977:
5971:
5969:
5963:
5961:
5955:
5954:
5952:
5948:
5943:
5936:
5931:
5929:
5924:
5922:
5917:
5916:
5913:
5899:
5896:
5894:
5891:
5890:
5889:
5888:
5884:
5882:
5881:
5877:
5872:
5871:
5868:
5862:
5859:
5857:
5854:
5852:
5849:
5847:
5844:
5842:
5839:
5837:
5834:
5833:
5831:
5827:
5817:
5814:
5810:
5807:
5806:
5805:
5802:
5798:
5795:
5794:
5793:
5790:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5762:
5761:
5758:
5757:
5755:
5753:
5752:
5747:
5741:
5740:Telluroketone
5738:
5736:
5733:
5732:
5730:
5728:
5724:
5718:
5715:
5713:
5710:
5708:
5705:
5703:
5700:
5698:
5695:
5694:
5692:
5690:
5686:
5680:
5677:
5675:
5672:
5671:
5669:
5667:
5663:
5657:
5654:
5652:
5649:
5647:
5644:
5642:
5639:
5637:
5634:
5632:
5629:
5627:
5626:Sulfonic acid
5624:
5622:
5619:
5617:
5616:Sulfinic acid
5614:
5612:
5611:Thiosulfonate
5609:
5607:
5604:
5602:
5601:Thiosulfinate
5599:
5597:
5596:Sulfenic acid
5594:
5592:
5589:
5587:
5584:
5580:
5577:
5576:
5575:
5572:
5570:
5567:
5566:
5564:
5562:
5558:
5552:
5551:Phosphaallene
5549:
5547:
5546:Phosphaalkyne
5544:
5542:
5541:Phosphaalkene
5539:
5535:
5532:
5531:
5530:
5527:
5525:
5522:
5520:
5517:
5515:
5512:
5508:
5505:
5504:
5503:
5500:
5496:
5493:
5492:
5491:
5488:
5487:
5485:
5483:
5479:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5453:
5450:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5371:
5368:
5366:
5363:
5362:
5361:
5358:
5357:
5355:
5353:
5349:
5346:
5326:
5314:
5311:
5310:
5309:
5306:
5302:
5299:
5297:
5294:
5293:
5292:
5289:
5288:
5286:
5282:
5276:
5273:
5271:
5268:
5264:
5261:
5260:
5259:
5256:
5252:
5249:
5247:
5244:
5242:
5239:
5238:
5237:
5234:
5233:
5231:
5229:
5225:
5219:
5216:
5214:
5213:Ethylenedioxy
5211:
5207:
5204:
5202:
5199:
5198:
5197:
5194:
5190:
5187:
5185:
5182:
5181:
5180:
5177:
5173:
5170:
5169:
5168:
5165:
5163:
5160:
5158:
5155:
5154:
5152:
5148:
5145:
5139:
5133:
5128:
5123:
5117:
5114:
5112:
5109:
5105:
5102:
5100:
5097:
5096:
5095:
5092:
5088:
5085:
5083:
5080:
5078:
5075:
5073:
5070:
5068:
5065:
5063:
5060:
5059:
5058:
5055:
5051:
5048:
5046:
5043:
5042:
5041:
5038:
5034:
5031:
5029:
5026:
5024:
5021:
5019:
5016:
5014:
5011:
5009:
5006:
5005:
5004:
5001:
5000:
4998:
4992:
4988:
4984:
4977:
4972:
4970:
4965:
4963:
4958:
4957:
4954:
4948:
4944:
4941:
4938:
4936:
4933:
4932:
4922:
4918:
4914:
4908:
4904:
4903:
4897:
4886:
4882:
4878:
4877:
4864:
4860:
4856:
4852:
4848:
4844:
4840:
4833:
4825:
4821:
4817:
4813:
4809:
4805:
4801:
4797:
4793:
4786:
4776:
4768:
4762:
4758:
4754:
4750:
4743:
4735:
4731:
4727:
4723:
4719:
4715:
4708:
4693:
4689:
4683:
4675:
4669:
4665:
4661:
4657:
4650:
4641:
4633:
4629:
4625:
4621:
4617:
4613:
4606:
4598:
4592:
4588:
4583:
4581:
4577:
4572:
4565:
4557:
4553:
4549:
4545:
4541:
4537:
4533:
4529:
4522:
4514:
4512:1-57259-153-6
4508:
4503:
4502:
4493:
4485:
4481:
4477:
4473:
4468:
4463:
4460:(2): 517â25.
4459:
4455:
4448:
4440:
4438:0-521-26796-X
4434:
4430:
4425:
4424:
4415:
4407:
4401:
4397:
4393:
4389:
4382:
4373:
4367:
4366:
4361:
4357:
4351:
4344:
4342:0-471-60180-2
4338:
4334:
4330:
4324:
4316:
4312:
4308:
4304:
4297:
4290:
4284:
4280:
4279:
4274:
4267:
4259:
4255:
4251:
4247:
4243:
4239:
4231:
4223:
4219:
4215:
4211:
4204:
4196:
4194:9780470771082
4190:
4186:
4182:
4178:
4171:
4165:
4161:
4155:
4139:
4135:
4131:
4124:
4109:
4102:
4095:
4079:
4075:
4071:
4065:
4046:
4042:
4036:
4032:
4028:
4021:
4019:
4017:
4008:
4002:
3998:
3994:
3990:
3989:
3981:
3979:
3977:
3975:
3973:
3971:
3969:
3961:
3959:0-534-16218-5
3955:
3951:
3947:
3941:
3925:
3921:
3915:
3899:
3895:
3891:
3885:
3877:
3876:
3871:
3865:
3861:
3850:
3846:
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3812:
3806:
3804:
3799:
3792:
3782:
3780:
3775:
3771:
3767:
3763:
3753:
3751:
3747:
3743:
3731:
3723:
3719:
3715:
3711:
3707:
3706:diglycolamine
3703:
3696:Gas treatment
3690:
3686:
3682:
3678:
3674:
3671:
3668:
3665:
3661:
3657:
3654:
3651:
3647:
3643:
3639:
3638:Nortriptyline
3636:
3633:
3629:
3625:
3621:
3617:
3616:Amitriptyline
3614:
3611:
3608:
3605:
3601:
3600:methcathinone
3597:
3593:
3590:
3587:
3586:phenylephrine
3583:
3580:
3577:
3574:
3571:
3570:antihistamine
3567:
3564:
3563:
3562:
3552:
3549:
3546:
3545:Sunset yellow
3543:
3540:
3538:
3537:Methyl orange
3535:
3534:
3533:
3531:
3516:
3514:
3510:
3493:
3484:
3482:
3478:
3474:
3470:
3466:
3462:
3446:
3443:
3439:
3435:
3431:
3427:
3423:
3419:
3415:
3411:
3390:
3380:
3377:
3375:
3368:
3364:
3362:
3357:
3353:
3350:
3346:
3344:
3339:
3338:Cope reaction
3335:
3331:
3329:
3324:
3320:
3316:
3314:
3309:
3305:
3302:
3296:
3292:
3289:
3286:Reduction of
3285:
3283:
3278:
3274:
3270:
3266:
3264:
3261:
3259:
3255:
3252:
3248:
3246:
3241:
3237:
3234:
3230:
3227:
3222:
3218:
3215:
3210:
3206:
3203:
3199:
3197:
3192:
3188:
3185:
3181:
3177:
3175:
3170:
3166:
3162:
3157:
3153:
3149:
3146:
3144:Reaction name
3143:
3142:
3139:
3131:
3115:
3107:
3102:
3093:
3085:
3073:
3060:
3041:
3030:
3013:
3001:
2988:
2980:
2975:
2972:
2958:
2954:
2950:
2946:
2942:
2920:
2912:
2908:
2892:
2876:
2868:
2854:
2838:
2829:
2817:
2810:
2799:
2785:
2780:
2762:
2750:
2745:
2729:
2721:
2714:
2702:
2697:
2662:
2654:
2647:
2635:
2630:
2615:
2603:
2598:
2590:
2582:
2568:
2564:
2560:
2556:
2552:
2548:
2539:
2537:
2536:azo compounds
2533:
2508:
2500:
2489:
2481:
2476:
2471:
2458:
2457:
2456:
2454:
2443:
2415:
2406:
2403:
2398:
2390:
2385:
2380:
2366:
2358:
2350:
2342:
2329:
2328:
2327:
2325:
2321:
2314:Diazotization
2288:
2275:
2259:
2251:
2240:
2227:
2226:
2225:
2223:
2219:
2191:
2179:
2167:
2156:
2147:
2138:
2116:
2096:
2078:
2035:
2012:
2006:
1997:
1988:
1980:
1972:
1954:
1936:
1919:
1907:
1891:
1888:
1877:
1869:
1847:
1838:
1826:
1815:
1811:
1790:
1772:
1748:
1732:
1731:
1730:
1728:
1717:
1713:
1708:
1706:
1702:
1693:
1689:
1687:
1683:
1679:
1675:
1671:
1667:
1663:
1644:intermediate
1643:
1639:
1635:
1631:
1628:
1623:
1619:
1616:
1614:
1609:
1605:
1602:intermediate
1601:
1597:
1593:
1589:
1586:
1584:
1580:
1575:
1571:
1567:
1565:
1560:
1556:
1552:
1550:
1545:
1541:
1537:
1533:
1529:
1527:
1522:
1518:
1514:
1512:
1507:
1503:
1500:
1498:
1493:
1489:
1485:
1481:
1479:
1478:Organic azide
1476:
1474:
1470:
1466:
1463:
1461:Reaction name
1460:
1459:
1456:
1448:
1431:
1427:
1425:
1420:
1418:
1405:
1401:
1397:
1393:
1389:
1385:
1384:hydrogenation
1375:
1373:
1368:
1366:
1364:
1359:
1349:
1347:
1342:
1340:
1336:
1332:
1328:
1323:
1292:
1283:
1272:
1265:
1250:
1241:
1233:
1230:
1219:
1218:
1217:
1186:
1178:
1170:
1154:
1146:
1135:
1134:
1133:
1131:
1124:From alcohols
1116:
1113:
1109:
1105:
1100:
1087:
1075:
1071:
1068:
1067:
1066:
1052:
1046:
1027:
1026:
1016:
1010:
991:
988:
987:
977:
971:
952:
949:
948:
938:
932:
925:
923:
919:
915:
914:
904:
898:
883:
880:
879:
869:
863:
856:
853:
852:
842:
839:
832:
829:
828:
818:
812:
805:
802:
801:
791:
788:
781:
780:Dimethylamine
778:
777:
767:
764:
757:
754:
753:
747:
744:
735:
732:
731:
728:
726:
716:
707:
705:
701:
698:-substituted
697:
693:
688:
686:
682:
678:
670:
669:electron pair
665:
651:
645:
640:
637:O. In their
625:
623:
619:
615:
574:
570:
562:
558:
553:
551:
547:
543:
539:
535:
523:
522:2-aminobutane
519:
515:
513:
506:
505:butan-1-amine
502:
498:
496:
491:
489:
485:
481:
477:
467:
465:
461:
453:
449:
445:
441:
437:
433:
432:Cyclic amines
430:
429:
428:
422:
418:
414:
411:
408:
407:diphenylamine
404:
400:
399:dimethylamine
396:
393:
390:
386:
383:
379:
375:
371:
367:
363:
359:
356:
355:
354:
352:
348:
344:
340:
328:
324:
321:
317:
314:
310:
309:
305:
302:
299:
295:
293:
289:
288:
283:
279:
269:
267:
264:, are called
262:RâC(=O)âNRâ˛Râł
259:
255:
250:
246:
236:
227:
223:
219:
215:
211:
207:
203:
199:
195:
191:
187:
183:
172:
168:
164:
160:
157:
153:
149:
143:
114:
72:
68:
59:
55:
51:
47:
40:
33:
19:
6610:(a strongly
6604:
6592:
6568:
6428:
6044:
6023:
5885:
5878:
5792:Vinyl halide
5749:
5679:Borinic acid
5674:Boronic acid
5651:Thioxanthate
5359:
4991:Hydrocarbons
4901:
4888:. Retrieved
4884:
4846:
4842:
4832:
4799:
4795:
4785:
4775:
4748:
4742:
4717:
4713:
4707:
4695:. Retrieved
4691:
4682:
4655:
4649:
4640:
4615:
4611:
4605:
4586:
4568:
4564:
4531:
4528:Biochemistry
4527:
4521:
4500:
4492:
4457:
4453:
4447:
4422:
4414:
4387:
4381:
4371:
4363:
4350:
4332:
4329:March, Jerry
4323:
4306:
4302:
4296:
4277:
4273:March, Jerry
4266:
4241:
4237:
4230:
4213:
4209:
4203:
4176:
4170:
4154:
4142:. Retrieved
4137:
4134:Spectroscopy
4133:
4123:
4111:. Retrieved
4107:
4094:
4082:. Retrieved
4073:
4064:
4052:. Retrieved
4045:the original
4030:
3986:
3949:
3940:
3928:. Retrieved
3924:the original
3914:
3902:. Retrieved
3893:
3884:
3873:
3864:
3788:
3759:
3699:
3628:clomipramine
3610:Thioridazine
3560:
3527:
3490:
3481:polypeptides
3473:salt bridges
3445:amino groups
3407:
3251:nitrous acid
3196:Sulfonamides
3137:
2955:hydrogen to
2943:
2781:
2563:formaldehyde
2545:
2529:
2439:
2320:nitrous acid
2317:
2215:
1709:
1701:sulfonamides
1698:
1659:
1638:formaldehyde
1454:
1428:
1421:
1381:
1369:
1362:
1355:
1352:From alkenes
1343:
1335:organohalide
1324:
1320:
1215:
1127:
1112:acetonitrile
1101:
1093:
1084:
1064:
921:
917:
745:
722:
713:
695:
689:
674:
659:Alkyl amines
644:propyl amine
631:
561:ammonium ion
554:
532:
511:
509:
494:
492:
475:
473:
457:
451:
447:
431:
426:
412:
394:
357:
334:
285:
281:
275:
251:
247:
237:
161:atom with a
70:
64:
54:
5856:Thiocyanate
5851:Sulfonamide
5816:Perchlorate
5804:Acyl halide
5765:Fluoroethyl
5646:Thionoester
5534:Phosphonium
5519:Phosphinate
5514:Phosphonous
5502:Phosphonate
5201:Hydroperoxy
5023:Cyclopropyl
4802:: 303â311.
4692:science.gov
4423:Nitrosation
4179:: 161â204.
4144:12 February
3820:Amine value
3716:(DIPA) and
3642:desipramine
3624:lofepramine
3592:Amphetamine
3477:carboxylate
3422:epinephrine
3410:amino acids
3347:Similar to
2218:sulfamation
2041:dehydration
1634:formic acid
1592:formic acid
1372:solid acids
1365:-octylamine
756:Methylamine
378:amino acids
374:methylamine
351:hydrocarbon
338:(see table)
202:amino acids
188:such as an
186:substituent
167:derivatives
6626:Categories
5760:Haloalkane
5631:Thioketone
5586:Persulfide
5482:Phosphorus
5447:Isocyanate
5437:Isonitrile
5338:or oxygen
5336:hydrogen,
5332:not being
5313:Orthoester
5206:Dioxiranes
5184:Enol ether
5072:1-Propenyl
4766:3527306730
4720:(6): 3â6.
4673:3527306730
4405:3527306730
4006:3527306730
3856:References
3803:strychnine
3791:ethylamine
3750:sweetening
3742:flue gases
3673:analgesics
3620:imipramine
3509:tryptophan
3442:Protonated
3361:Isonitrile
3269:pyridinium
3228:compounds
3200:Reagents:
3178:Reagents:
1398:including
1130:alkylation
831:Ethylamine
700:aziridines
622:conjugated
569:solubility
488:tetraamine
444:piperidine
380:, and the
5893:inorganic
5727:Tellurium
5641:Thioester
5606:Sulfoxide
5591:Disulfide
5579:Sulfonium
5529:Phosphine
5507:Phosphite
5490:Phosphate
5422:Carbamate
5397:Hydrazone
5330:element,
5328:Only one
5301:Anhydride
5040:Methylene
4921:915134542
4863:0021-8995
4824:1385-8947
4734:0369-9420
4580:CC BY 4.0
4462:CiteSeerX
3646:amoxapine
3582:Ephedrine
3438:histamine
3434:serotonin
3267:Reagent:
3249:Reagent:
3231:Reagent:
3049:⇀
3042:−
3031:−
3024:↽
2862:⟶
2763:−
2738:⟶
2623:⟶
2555:aldehydes
2495:⟶
2490:−
2442:diazonium
2399:−
2373:⟶
2268:⟶
2192:⏟
2157:⏟
2139:−
2132:‖
2117:−
2013:⏟
2007:−
1998:−
1973:−
1908:−
1889:−
1878:⏟
1870:−
1863:‖
1848:−
1816:⏟
1749:−
1651:Reactions
1613:Haloamine
1583:aldehydes
1464:Substrate
1259:⟶
1163:⟶
1119:Synthesis
654:Structure
440:aziridine
405:would be
353:groups):
218:Inorganic
163:lone pair
148:compounds
67:chemistry
6377: /
6340: /
6324: /
6295: /
6279: /
6272: /
6247: /
6235: /
6204: /
6192: /
6180: /
6153: /
6053:>C=NR
5950:Hydrides
5942:Nitrogen
5874:See also
5809:Chloride
5735:Tellurol
5689:Selenium
5656:Xanthate
5370:Ammonium
5352:Nitrogen
5334:carbon,
5291:Carboxyl
5258:Aldehyde
5246:Acryloyl
5228:carbonyl
5132:hydrogen
5087:Cumulene
4943:Archived
4632:21504168
4582:license.
4556:30690389
4358:(1943).
4331:(1992),
4275:(2007),
4258:15675863
4078:Archived
3948:(1992),
3930:28 March
3904:28 March
3898:Archived
3809:See also
3700:Aqueous
3689:tertiary
3677:morphine
3675:such as
3530:azo dyes
3513:tyrosine
3492:Hormones
3461:proteins
3430:dopamine
3301:anilines
3150:Comment
3134:Overview
3094:′
3014:′
2951:with an
2945:Mercuric
2909:′
2869:″
2830:″
2818:′
2784:enamines
2751:′
2703:′
2636:′
2604:′
2557:to form
2534:to form
2036:→
1536:nitriles
1467:Comment
1388:nitriles
1284:′
1266:′
1242:′
719:Basicity
685:kcal/mol
679:for the
614:solvents
484:triamine
370:aromatic
292:aromatic
278:nitrogen
254:nitrogen
198:nitrogen
182:hydrogen
159:nitrogen
6400:Halides
6038:Organic
5944:species
5898:organic
5697:Selenol
5621:Sulfone
5574:Sulfide
5472:NONOate
5467:Nitroso
5457:Nitrite
5452:Nitrate
5442:Cyanate
5432:Nitrile
5417:Amidine
5412:Imidate
5382:Nitrene
5377:Hydrazo
5365:Enamine
5296:Acetoxy
5284:carboxy
5251:Benzoyl
5189:Epoxide
5172:Methoxy
5162:Alcohol
5116:Carbene
5050:Methine
4890:22 July
4804:Bibcode
4697:1 March
4548:2207096
4484:9512720
4140:: 22â25
4113:7 March
4054:26 June
3870:"amine"
3712:(DEA),
3708:(DGA),
3704:(MEA),
3691:amines.
3681:codeine
3551:Ponceau
3416:. Many
3226:Nitroso
3160:Amines
2957:iminium
2567:trimers
2551:ketones
2324:aniline
1666:ligands
1640:via an
1598:via an
1596:ammonia
1579:Ketones
1430:Aniline
1410:group.
884:(4-MeOC
855:Aniline
618:aniline
480:diamine
389:aniline
376:, most
362:ammonia
347:ammonia
222:ammonia
214:aniline
171:ammonia
119:UK also
6632:Amines
6614:oxide)
6612:acidic
6143:Oxides
5797:Iodide
5717:Selone
5561:Sulfur
5270:Ketone
5263:Ketene
5241:Acetyl
5196:Peroxy
5167:Alkoxy
5157:Acetal
5138:oxygen
5127:carbon
5111:Alkyne
5104:Benzyl
5099:Phenyl
5082:Allene
5077:Crotyl
5057:Alkene
5045:Bridge
5033:Pentyl
5018:Propyl
5008:Methyl
4919:
4909:
4861:
4822:
4780:London
4763:
4732:
4670:
4630:
4593:
4554:
4546:
4509:
4482:
4464:
4435:
4402:
4339:
4285:
4256:
4191:
4084:23 May
4048:(Book)
4037:
4003:
3956:
3830:Ammine
3785:Safety
3728:) and
3685:heroin
3683:, and
3670:Opiate
3644:, and
3598:, and
3568:is an
3465:lysine
3436:, and
3343:Alkene
3328:Alkene
3214:Imines
2959:ions:
2953:α
2559:imines
2532:phenol
1896:
1727:amides
1684:(the "
1682:amides
1626:Amine
1400:oximes
1396:imines
1392:azides
1110:, and
1048:
1012:
973:
934:
926:(PhNMe
900:
865:
840:10.63
814:
789:10.64
765:10.62
692:chiral
546:methyl
538:methyl
495:-amine
464:anions
436:Cyclic
343:carbon
294:ring.
266:amides
212:, and
146:) are
71:amines
6582:, 0,
6274:(HON)
6058:-CONR
5829:Other
5666:Boron
5636:Thial
5569:Thiol
5462:Nitro
5427:Imide
5407:Amide
5392:Oxime
5387:Imine
5360:Amine
5308:Ester
5275:Ynone
5179:Ether
5150:R-O-R
5125:Only
5067:Allyl
5062:Vinyl
5028:Butyl
5013:Ethyl
5003:Alkyl
4849:(2).
4552:S2CID
4104:(PDF)
3849:IUPAC
3557:Drugs
3475:with
3174:Amide
2198:water
2163:amide
1822:amine
1712:acids
1642:imine
1632:with
1600:imine
1590:with
1549:Amide
1534:with
1526:Imine
1511:Imine
1413:LiAlH
1404:nitro
1050:2.75
1014:1.00
992:(4-NO
975:2.46
953:(3-NO
936:5.07
902:5.36
867:4.62
857:(PhNH
833:(EtNH
816:9.76
758:(MeNH
725:bases
550:ethyl
542:ethyl
512:amino
366:alkyl
190:alkyl
156:basic
61:Amine
50:Anime
6541:NHBr
6533:NHCl
6326:ONOO
6155:(NO)
6108:HNCS
6103:HNCO
6098:HOCN
6081:(CN)
5751:Halo
5236:Acyl
5136:and
5094:Aryl
4917:OCLC
4907:ISBN
4892:2021
4859:ISSN
4820:ISSN
4761:ISBN
4730:ISSN
4699:2022
4668:ISBN
4628:PMID
4591:ISBN
4576:text
4544:PMID
4507:ISBN
4480:PMID
4433:ISBN
4400:ISBN
4337:ISBN
4283:ISBN
4254:PMID
4189:ISBN
4146:2024
4115:2024
4086:2021
4056:2018
4035:ISBN
4001:ISBN
3954:ISBN
3932:2017
3906:2017
3772:and
3687:are
3658:and
3648:are
3630:are
3626:and
3584:and
3524:Dyes
3392:HgCl
3387:and
2553:and
2048:heat
1892:>
1688:").
1676:and
1636:and
1594:and
1581:and
1363:tert
1104:DMSO
1054:5.62
1018:1.00
979:2.88
940:1.17
906:2.29
871:4.17
844:4.27
820:5.75
793:4.37
786:NH)
769:4.17
548:and
540:and
421:EDTA
385:tris
230:NClH
194:aryl
150:and
46:Amin
6602:,
6549:NHI
6525:NHF
6479:BrN
6471:ClN
6447:NBr
6439:NCl
6435:(?)
6346:NOO
6310:NNO
6270:HNO
6230:HNO
6206:(NO
6175:HNO
6130:-NO
6125:-NO
6093:NCN
6071:HCN
6066:-CN
6030:(?)
5402:Azo
4851:doi
4847:140
4812:doi
4800:356
4753:doi
4722:doi
4660:doi
4620:doi
4536:doi
4472:doi
4458:276
4392:doi
4311:doi
4246:doi
4218:doi
4181:doi
4160:doi
3993:doi
3724:(CO
3604:DEA
3547:FCF
3511:or
3497:âNH
3469:DNA
3449:âNH
3091:CHR
2998:NCH
2767:NHR
2579:RNH
2355:HNO
2339:ANH
2285:NSO
2003:COO
1408:âCN
1167:RNH
1144:ROH
1108:DMF
810:N)
806:(Me
782:(Me
740:of
577:RNH
368:or
280:.
240:âNH
235:).
192:or
169:of
65:In
48:or
6628::
6606:+5
6600:+4
6598:,
6594:+3
6590:,
6588:+2
6586:,
6584:+1
6580:â1
6578:,
6576:â2
6574:,
6570:â3
6520:Cl
6516:NH
6495:NH
6487:IN
6463:FN
6455:NI
6429:NF
6420:NF
6412:NF
6407:NF
6351:NO
6335:NO
6331:HO
6322:NO
6318:HO
6262:NO
6249:NO
6237:NO
6199:NO
6194:NO
6182:NO
6151:NO
6113:CH
6076:CN
6045:NR
6024:NH
6007:HN
5990:OH
5986:NH
5973:NH
5965:NH
5957:NH
5134:,
5129:,
4915:.
4883:.
4857:.
4845:.
4841:.
4818:.
4810:.
4798:.
4794:.
4759:.
4728:.
4718:24
4716:.
4690:.
4666:.
4658:.
4626:.
4616:54
4614:.
4550:.
4542:.
4532:29
4530:.
4478:.
4470:.
4456:.
4398:.
4390:.
4369:;
4362:.
4307:51
4305:.
4252:.
4242:70
4240:.
4214:79
4212:.
4187:.
4138:34
4132:.
4106:.
4072:.
4029:.
4015:^
3999:.
3967:^
3896:.
3892:.
3872:.
3805:.
3797:50
3795:LD
3764:,
3752:.
3732:(H
3679:,
3640:,
3622:,
3618:,
3594:,
3515:.
3440:.
3432:,
3428:,
3424:,
3382:CS
3182:,
3058:Hg
2969:Hg
2889:NR
2873:CH
2835:CH
2808:NH
2786::
2759:CH
2719:NR
2652:NR
2569::
2498:AY
2468:AN
2377:AN
2370:HX
2256:SO
2249:NH
1874:OH
1729:.
1723:NH
1538:.
1486:.
1442:NH
1394:,
1390:,
1374:.
1367:.
1348:.
1341:.
1289:NH
1281:RR
1270:NH
1263:RR
1247:NH
1228:RX
1151:NH
1106:,
1058:10
1044:)
1040:NH
1022:10
1008:)
1004:NH
996:-C
983:10
969:)
965:NH
957:-C
944:10
930:)
910:10
896:)
892:NH
875:10
861:)
848:10
837:)
824:10
797:10
773:10
762:)
736:pK
598:NH
497:.
486:,
482:,
466:.
446:.
216:.
208:,
204:,
175:NH
136:iË
130:eÉŞ
117:,
107:iË
89:iË
69:,
6551:2
6543:2
6535:2
6527:2
6518:2
6510:2
6508:F
6506:2
6504:N
6499:F
6497:2
6489:3
6481:3
6473:3
6465:3
6457:3
6449:3
6441:3
6431:5
6422:3
6414:2
6388:3
6383:O
6381:2
6379:N
6374:4
6372:O
6370:2
6368:N
6366:4
6364:H
6356:4
6344:2
6342:O
6337:2
6333:2
6320:2
6312:2
6308:2
6306:H
6301:O
6299:2
6297:N
6290:2
6285:O
6283:2
6281:N
6276:2
6264:3
6254:2
6242:3
6232:3
6224:5
6222:O
6220:2
6218:N
6212:2
6210:)
6208:2
6201:2
6187:2
6177:2
6169:3
6167:O
6165:2
6163:N
6157:2
6132:2
6119:2
6117:N
6115:2
6091:2
6089:H
6083:2
6060:2
6047:3
6026:5
6017:3
6015:N
6009:3
6001:4
5999:H
5997:2
5995:N
5988:2
5981:N
5975:2
5967:4
5959:3
5934:e
5927:t
5920:v
4975:e
4968:t
4961:v
4923:.
4894:.
4865:.
4853::
4826:.
4814::
4806::
4769:.
4755::
4736:.
4724::
4701:.
4676:.
4662::
4634:.
4622::
4599:.
4558:.
4538::
4515:.
4486:.
4474::
4441:.
4408:.
4394::
4376:.
4317:.
4313::
4260:.
4248::
4224:.
4220::
4197:.
4183::
4162::
4148:.
4117:.
4088:.
4058:.
4009:.
3995::
3934:.
3908:.
3851:)
3738:2
3734:2
3726:2
3666:.
3606:.
3502:3
3454:3
3447:(
3394:2
3384:2
3116:+
3112:H
3108:+
3103:+
3098:]
3086:=
3082:N
3074:2
3070:R
3066:[
3061:+
3011:R
3002:2
2989:2
2985:R
2981:+
2976:+
2973:2
2929:O
2921:2
2917:H
2913:+
2906:R
2901:)
2893:2
2885:(
2881:C
2877:=
2866:R
2859:O
2855:=
2851:C
2847:)
2839:2
2827:R
2823:(
2815:R
2811:+
2800:2
2796:R
2746:2
2742:R
2730:2
2726:H
2722:+
2715:=
2711:C
2698:2
2694:R
2671:O
2663:2
2659:H
2655:+
2648:=
2644:C
2631:2
2627:R
2620:O
2616:=
2612:C
2599:2
2595:R
2591:+
2583:2
2509:2
2505:N
2501:+
2486:Y
2482:+
2477:+
2472:2
2448:2
2446:N
2424:O
2416:2
2412:H
2407:2
2404:+
2395:X
2391:+
2386:+
2381:2
2367:+
2359:2
2351:+
2343:2
2297:H
2289:3
2276:2
2272:R
2260:3
2252:+
2241:2
2237:R
2188:O
2180:2
2176:H
2168:+
2148:3
2144:R
2128:O
2123:C
2107:|
2097:1
2093:R
2079:2
2075:R
2069:|
2064:N
1989:3
1985:R
1981:+
1977:H
1965:|
1955:1
1951:R
1937:2
1933:R
1927:|
1920:+
1916:N
1904:H
1859:O
1854:C
1839:3
1835:R
1827:+
1812::
1801:|
1791:1
1787:R
1773:2
1769:R
1763:|
1758:N
1745:H
1721:3
1719:R
1444:2
1440:5
1438:H
1436:6
1434:C
1432:(
1415:4
1305:X
1301:]
1293:2
1277:[
1273:+
1251:2
1239:R
1234:2
1231:+
1195:O
1187:2
1183:H
1179:+
1171:2
1155:3
1147:+
1097:b
1056:Ă
1042:2
1038:4
1036:H
1034:6
1032:C
1030:3
1020:Ă
1006:2
1002:4
1000:H
998:6
994:2
981:Ă
967:2
963:4
961:H
959:6
955:2
942:Ă
928:2
922:N
920:,
918:N
908:Ă
894:2
890:4
888:H
886:6
873:Ă
859:2
846:Ă
835:2
822:Ă
808:3
795:Ă
784:2
771:Ă
760:2
749:b
746:K
738:a
702:(
696:N
648:2
635:2
633:D
610:3
603:2
594:2
589:R
582:3
565:3
563:R
476:N
452:N
448:N
434:â
423:.
409:.
391:.
242:2
232:2
228:(
177:3
173:(
142:/
139:n
133:m
127:Ë
124:/
113:/
110:n
104:m
101:ĂŚ
98:Ë
95:,
92:n
86:m
83:Ë
80:É
77:/
73:(
52:.
41:.
34:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
