1004:
1495:(around) to them. Carbon satellites are small because only very few of the molecules in the sample have that carbon as the rare NMR-active C isotope. As always for coupling due to a single spin-1/2 nucleus, the signal splitting for the H attached to the C is a doublet. The H attached to the more abundant C is not split, so it is a large singlet. The net result is a pair of evenly spaced small signals around the main one. If the H signal would already be split due to H–H coupling or other effects, each of the satellites would also reflect this coupling as well (as usual for complex splitting patterns due to dissimilar coupling partners). Other NMR-active nuclei can also cause these satellites, but carbon is most common culprit in the proton NMR spectra of organic compounds.
1446:
constant, then a triplet of doublets is seen. In the example below, the triplet coupling constant is larger than the doublet one. By convention the pattern created by the largest coupling constant is indicated first and the splitting patterns of smaller constants are named in turn. In the case below it would be erroneous to refer to the quartet of triplets as a triplet of quartets. The analysis of such multiplets (which can be much more complicated than the ones shown here) provides important clues to the structure of the molecule being studied.
1095:
1025:
1176:. The first proton will split the peak into two equal intensities and will go from one peak at 2.5 ppm to two peaks, one at 2.5 ppm + 3.5 Hz and the other at 2.5 ppm - 3.5 Hz—each having equal intensities. However these will be split again by the second proton. The frequencies will change accordingly:
1465:
If there are other NMR-active nuclei present in a molecule, spin-spin coupling will be observed between the hetero-atoms and the protons. This occurs most frequently in compounds that contain phosphorus or fluorine, as they are both spin 1/2 nuclei of 100% abundance. For example, the 1H signals for
1445:
When a proton is coupled to two different protons, then the coupling constants are likely to be different, and instead of a triplet, a doublet of doublets will be seen. Similarly, if a proton is coupled to two other protons of one type, and a third of another type with a different, smaller coupling
1474:
Even larger coupling constants may be seen in phosphines, especially if the proton is directly bonded to the phosphorus. Coupling constants for these protons are often as large as 200 Hz, for example in diethylphosphine, where the 1J P-H coupling constant is 190 Hz. These coupling constants are so
1456:
The simple rules for the spin-spin splitting of NMR signals described above apply only if the chemical shifts of the coupling partners are substantially larger than the coupling constant between them. Otherwise there may be more peaks, and the intensities of the individual peaks will be distorted
1470:
are split into a doublet by the fluorine atom; conversely the fluorine-19 NMR spectrum of this compound shows a quartet due to being split by the three protons. Typical 2J coupling constants between fluorine and protons are 48 Hz or so; the strength of coupling declines to 2 Hz in 4J coupling.
1434:
peaks according to the (n + 1) rule of multiplicity. Below are NMR signals corresponding to several simple multiplets of this type. Note that the outer lines of the nonet (which are only 1/8 as high as those of the second peak) can barely be seen, giving a superficial resemblance to a septet.
1011:
The integrated intensities of NMR signals are, ideally, proportional to the ratio of the nuclei within the molecule. Together with chemical shift and coupling constants, the integrated intensities allow structural assignments. For mixtures, the signal intensities can be used to determine molar
1137:
In another molecule a proton resonates at 2.5 ppm and that proton would also be split into two by the proton at 1 ppm. Because the magnitude of interaction is the same the splitting would have the same coupling constant 7 Hz apart. The spectrum would have two signals, each being a
1079:, NMR spectra allow structural assignments by virtue of spin-spin coupling (and integrated intensities). Because nuclei themselves possess a small magnetic field, they influence each other, changing the energy and hence frequency of nearby nuclei as they resonate—this is known as
1589:
1106:
The effect of scalar coupling can be understood by examination of a proton which has a signal at 1 ppm. This proton is in a hypothetical molecule where three bonds away exists another proton (in a CH-CH group for instance), the neighbouring group (a
1195:
The net result is not a signal consisting of 4 peaks but three: one signal at 7 Hz above 2.5 ppm, two signals occur at 2.5 ppm, and a final one at 7 Hz below 2.5 ppm. The ratio of height between them is 1:2:1. This is known as a
262:
to keep the resonance frequency constant. Additionally, the deuterium signal may be used to accurately define 0 ppm as the resonant frequency of the lock solvent and the difference between the lock solvent and 0 ppm (TMS) are well known.
1637:
Baccolini, Graziano; Boga, Carla; Mazzacurati, Marzia; Sangirardi, Federico (2006-04-01). "High Atom-Economical One-Pot
Synthesis of Secondary Phosphines and Their Borane Complexes Using Recycling Phosphorus Donor Reagent".
1003:
1506:. These are experimental artifacts from the spectroscopic analysis itself, not an intrinsic feature of the spectrum of the chemical and not even specifically related to the chemical or its structure.
1868:
1858:
1451:
1440:
1833:
1823:
1873:
1808:
20:
1848:
1483:
Occasionally, small peaks can be seen shouldering the main H NMR peaks. These peaks are not the result of proton-proton coupling, but result from the coupling of H atoms to an adjoining
477:(HSQC) experiment, which correlates protons and carbons that are one bond away from each other. A hydrogen that is not attached to a carbon can be identified because it does not have a
208:
Deuterated solvents permit the use of deuterium frequency-field lock (also known as deuterium lock or field lock) to offset the effect of the natural drift of the NMR's magnetic field
1126:
The coupling constant is independent of magnetic field strength because it is caused by the magnetic field of another nucleus, not the spectrometer magnet. Therefore, it is quoted in
1430:
CH, as another example: the CH proton is attached to three identical methyl groups containing a total of 9 identical protons. The C-H signal in the spectrum would be split into
1091:, and can typically be seen up to three bonds away (3-J coupling), although it can occasionally be visible over four to five bonds, though these tend to be considerably weaker.
1164:
peak will be split into a doublet by the CH peak—with one peak at 1 ppm + 3.5 Hz and one at 1 ppm - 3.5 Hz (total splitting or coupling constant is 7 Hz).
343:. Nuclei tend to be deshielded by groups which withdraw electron density. Deshielded nuclei resonate at higher δ values, whereas shielded nuclei resonate at lower δ values.
1007:
H NMR spectrum predicted for 1,4-dimethylbenzene. Under ideal conditions, the ratio of integrated signal of protons A and B is related to the structure of this molecule.
260:
233:
1475:
large that they may span distances in excess of 1ppm (depending on the spectrometer), making them prone to overlapping with other proton signals in the molecule.
1499:
1828:
1818:
1529:
235:. In order to provide deuterium lock, the NMR constantly monitors the deuterium signal resonance frequency from the solvent and makes changes to the
197:, making sample recovery easy as well. Modern spectrometers are able to reference spectra based on the residual proton in the solvent (e.g. the CHCl
1894:
1012:
ratios. These considerations are valid only when sufficient time is allowed for full relaxation of the affected signals, as determined by their T
1566:
1729:
478:
1115:
higher than 1 ppm and the other peak being the same number of hertz lower than 1 ppm. These peaks each have half the area of the former
434:) have no characteristic chemical shift. However, such resonances can be identified by the disappearance of a peak when reacted with
1838:
1766:
1863:
1775:
193:
molecule, with all protons being chemically equivalent, giving one single signal, used to define a chemical shift = 0 ppm. It is
1843:
474:
1681:
Gottlieb HE; Kotlyar V; Nudelman A (October 1997). "NMR Chemical Shifts of Common
Laboratory Solvents as Trace Impurities".
1853:
1813:
1739:
1803:
1587:, Donald C. Hofer; Vincent N. Kahwaty; Carl R. Kahwaty, "NMR field frequency lock system", issued 1978-08-29
1607:
1016:
values. A further complication arises from the difficulty of integrating signals of very different line shapes.
315:, are not precise, but typical - they are to be therefore regarded mainly as a reference. Deviations are in ±0.2
190:
139:
1759:
65:
1724:
1620:
1584:
1570:
1223:, keeping the chemical shift and coupling constants identical, the following changes are observed:
290:
1752:
1488:
319:
range, sometimes more. The exact value of chemical shift depends on molecular structure and the
83:
of a substance, in order to determine the structure of its molecules. In samples where natural
1145:
The two doublets at 1 ppm and 2.5 ppm from the fictional molecule CH-CH are now changed into CH
1142:. Each doublet will have the same area because both doublets are produced by one proton each.
473:) is used. An alternate method for identifying protons that are not attached to carbons is the
194:
1119:
peak. The magnitude of this splitting (difference in frequency between peaks) is known as the
1102:(blue bar). The 1:1:1 triplet for HD arises from heteronuclear (different isotopes) coupling.
110:(deuterium = H, often symbolized as D) solvents especially for use in NMR are preferred, e.g.
336:
151:
416:
hybridized carbon atoms to an aliphatic chain. This causes a downfield shift of 1–2 ppm at C
1277:
238:
211:
159:
99:
1024:
285:
consists of a triplet at 1.5 ppm and a quartet at 3.5 ppm in a 3:2 ratio. The spectrum of
8:
177:
Historically, deuterated solvents were supplied with a small amount (typically 0.1%) of
1080:
271:
42:
1698:
1663:
1655:
1603:
1518:
1509:
Carbon satellites and spinning sidebands should not be confused with impurity peaks.
462:
protons may also be suppressed when a solvent containing acidic deuterium ions (e.g.
340:
332:
316:
182:
178:
1051:) group are not coupling with the other H atoms and appear as a singlet, but the -CH
1690:
1647:
167:
69:
1899:
1450:
1071:) are coupling with each other, resulting in a quartet and triplet respectively.
1523:
1439:
1131:
1108:
1076:
1036:
401:
359:
328:
308:
282:
267:
186:
76:
34:
1744:
1123:. A typical coupling constant value for aliphatic protons would be 7 Hz.
1888:
1798:
1659:
1467:
1088:
1032:
409:
297:
1702:
1667:
37:(in ppm on the horizontal axis). Signals from spectrum have been assigned
1719:
1111:) causes the signal at 1 ppm to split into two, with one peak being a few
300:, proton NMR is a powerful tool for molecular structure characterization.
19:
1602:
Balci, M., in "Basic H- and C-NMR Spectroscopy" (1st
Edition, Elsevier),
1060:
435:
351:
324:
111:
1120:
447:
431:
73:
30:
1734:
1694:
1651:
1272:
identical protons into components whose sizes are in the ratio of the
1492:
1484:
1191:
3.5 Hz signal will be split into 2.5 ppm and 2.5 ppm - 7 Hz
1184:
3.5 Hz signal will be split into 2.5 ppm + 7 Hz and 2.5 ppm
443:
386:
107:
80:
1261:
Something split by three identical protons takes a shape known as a
1503:
1040:
463:
370:
347:
275:
131:
84:
38:
1636:
1043:
atoms in ethyl acetate regarding NMR. The hydrogens (H) on the CH
278:
for each proton reflects the abundance of the individual protons.
266:
Proton NMR spectra of most organic compounds are characterized by
1779:
1094:
1048:
366:
320:
286:
119:
103:
88:
27:
1098:
H NMR spectrum of a solution of HD (labeled with red bars) and H
459:
405:
389:
355:
92:
1680:
331:
in which the spectrum is being recorded and other neighboring
205:). Deuterated solvents are now commonly supplied without TMS.
1407:+1 components, this type of splitting is said to follow the "
1127:
1112:
424:
369:. These cause a downfield shift of approximately 2–4 ppm for
1200:
and is an indicator that the proton is three-bonds from a CH
1498:
Sometimes other peaks can be seen around H peaks, known as
1478:
392:
atom directly bonded to the substituent in question, and C
339:
of the atom to which the hydrogen atom is attached and to
87:(H) is used, practically all the hydrogen consists of the
1491:
as they are small and appear around the main H peak i.e.
483:
281:
Simple molecules have simple spectra. The spectrum of
1087:. This interaction between two nuclei occurs through
241:
214:
1548:
R. M. Silverstein, G. C. Bassler and T. C. Morrill,
1526:– letter designations for coupled spin-systems
1265:, each peak having relative intensities of 1:3:3:1.
1168:
In consequence the CH peak at 2.5 ppm will be split
1530:
Nuclear magnetic resonance spectroscopy of proteins
346:Examples of electron withdrawing substituents are
254:
227:
1550:Spectrometric Identification of Organic Compounds
1886:
289:consists of a single peak at 7.2 ppm due to the
33:plotted as signal intensity (vertical axis) vs.
1774:
1157:peak will be twice that of the 2.5 ppm CH peak.
158:. However, a solvent without hydrogen, such as
1760:
1767:
1753:
1502:and are related to the rate of spin of an
1460:
1083:. The most important type in basic NMR is
106:protons must not be allowed to interfere.
1487:(C) atom. These small peaks are known as
377:and of less than 1–2 ppm for H atoms on C
1621:"Coupling of Protons with Fluorine Page"
1479:Carbon satellites and spinning sidebands
1093:
1023:
1002:
18:
1895:Nuclear magnetic resonance spectroscopy
1725:Spectral Database for Organic Compounds
1242:is coupled to two protons into a 1:2:1
335:. Hydrogen nuclei are sensitive to the
1887:
1039:. There are three different types of
1019:
475:heteronuclear single quantum coherence
1748:
1735:Extensive set of educational examples
998:
98:Simple NMR spectra are recorded in
41:atom groups (a through j) from the
13:
1415:neighbors appears as a cluster of
396:is an aliphatic C atom bonded to C
303:
270:in the range +14 to -4 ppm and by
16:NMR via protons, hydrogen-1 nuclei
14:
1911:
1713:
1227:The relative areas between the CH
189:of each analyte proton. TMS is a
50:Proton nuclear magnetic resonance
1741:1D Proton NMR] 1D NMR experiment
1449:
1438:
1035:plotted as signal intensity vs.
982:
979:
968:
965:
954:
951:
943:
725:
26:(1-dimensional) of a mixture of
423:Note that labile protons (-OH,
1674:
1630:
1613:
1596:
1577:
1559:
1542:
1207:This can be extended to any CH
1153:The total area of the 1 ppm CH
450:atom. This method is called a
1:
1720:H-NMR Interpretation Tutorial
1535:
140:deuterated dimethyl sulfoxide
91:H (hydrogen-1; i.e. having a
7:
1512:
10:
1916:
1215:-CH group is changed to CH
1172:by each proton from the CH
66:nuclear magnetic resonance
1786:
1583:
1422:With 2-methylpropane, (CH
1393:1 8 28 56 70 56 28 8 1
1130:(frequency) and not ppm (
1457:(second-order effects).
1411:+1 rule": a proton with
949:=O (aliphatic aldehyde)
291:diamagnetic ring current
64:) is the application of
1461:Hetero-nuclear coupling
1382:1 7 21 35 35 21 7 1
963:=O (aromatic aldehyde)
1730:Proton Chemical Shifts
1103:
1072:
1029:Example H NMR spectrum
1008:
481:in the HSQC spectrum.
311:values, symbolized by
256:
229:
201:, 0.01% in 99.99% CDCl
46:
24:Example H NMR spectrum
1585:US patent 4110681
1235:subunits will be 3:2.
1097:
1027:
1006:
274:between protons. The
257:
255:{\displaystyle B_{0}}
230:
228:{\displaystyle B_{0}}
152:deuterated chloroform
22:
1371:1 6 15 20 15 6 1
977:M-H (metal hydride)
239:
212:
185:for referencing the
174:, may also be used.
160:carbon tetrachloride
45:shown at upper left.
1268:A peak is split by
1031:(1-dimensional) of
1020:Spin-spin couplings
1552:, 5th Ed., Wiley,
1500:spinning sidebands
1211:group. When the CH
1104:
1081:spin-spin coupling
1073:
1009:
341:electronic effects
272:spin-spin coupling
252:
225:
47:
1882:
1881:
1695:10.1021/jo971176v
1689:(21): 7512–7515.
1652:10.1021/ol060284d
1519:Mass spectrometry
1489:carbon satellites
1397:
1396:
1360:1 5 10 10 5 1
1278:Pascal's triangle
1121:coupling constant
1059:hydrogens of the
996:
995:
487:Functional group
333:functional groups
276:integration curve
183:internal standard
179:tetramethylsilane
1907:
1776:NMR spectroscopy
1769:
1762:
1755:
1746:
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1707:
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1672:
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1646:(8): 1677–1680.
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1569:. Archived from
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999:Signal intensity
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988:
484:
261:
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234:
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231:
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168:carbon disulfide
112:deuterated water
95:for a nucleus).
72:with respect to
70:NMR spectroscopy
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1567:"ChemicalShift"
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1466:the protons in
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1234:
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1222:
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1101:
1085:scalar coupling
1075:In addition to
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446:will replace a
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304:Chemical shifts
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1714:External links
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1608:978-0444518118
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1573:on 2016-03-06.
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408:fragments and
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329:magnetic field
309:Chemical shift
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296:Together with
283:ethyl chloride
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118:O, deuterated
115:
58:hydrogen-1 NMR
35:chemical shift
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1580:
1572:
1568:
1562:
1555:
1551:
1545:
1541:
1531:
1528:
1525:
1522:
1520:
1517:
1516:
1510:
1507:
1505:
1501:
1496:
1494:
1490:
1486:
1476:
1472:
1469:
1468:fluoromethane
1458:
1454:
1452:
1447:
1443:
1441:
1436:
1433:
1420:
1418:
1414:
1410:
1406:
1402:
1392:
1389:
1386:
1385:
1381:
1378:
1375:
1374:
1370:
1367:
1364:
1363:
1359:
1356:
1353:
1352:
1348:
1345:
1342:
1341:
1337:
1334:
1331:
1330:
1326:
1323:
1320:
1319:
1315:
1312:
1309:
1308:
1304:
1301:
1298:
1297:
1293:
1290:
1288:
1285:
1284:
1281:
1279:
1275:
1271:
1266:
1264:
1256:
1248:
1246:around 1 ppm.
1245:
1237:
1226:
1225:
1224:
1205:
1199:
1190:
1186:
1183:
1179:
1178:
1177:
1171:
1159:
1152:
1151:
1150:
1143:
1141:
1135:
1133:
1129:
1124:
1122:
1118:
1114:
1110:
1096:
1092:
1090:
1086:
1082:
1078:
1062:
1050:
1042:
1038:
1034:
1033:ethyl acetate
1030:
1026:
1017:
1005:
985:
976:
975:
971:
962:
961:
957:
948:
947:
940:
937:
934:
933:
929:
926:
923:
920:
919:
915:
912:
909:
903:
902:
898:
895:
892:
889:
888:
884:
881:
878:
872:
871:
867:
864:
861:
851:
850:
846:
843:
840:
834:
833:
829:
826:
823:
817:
816:
812:
809:
806:
803:
802:
798:
795:
792:
786:
785:
781:
778:
775:
772:
771:
767:
764:
761:
758:
757:
753:
750:
747:
744:
743:
739:
736:
733:
730:
729:
722:
719:
713:
712:
708:
705:
702:
692:
691:
687:
684:
681:
678:
677:
673:
670:
667:
657:
656:
652:
649:
646:
643:
642:
638:
635:
632:
629:
628:
624:
621:
618:
615:
614:
610:
607:
604:
601:
600:
596:
593:
590:
587:
586:
582:
579:
576:
573:
572:
568:
565:
562:
552:
551:
547:
544:
541:
538:
537:
533:
530:
527:
524:
523:
519:
516:
513:
506:
505:
501:
495:
489:
486:
485:
482:
480:
476:
469:
465:
461:
457:
449:
445:
441:
433:
429:
421:
415:
411:
407:
403:
391:
388:
372:
368:
364:
357:
353:
349:
344:
342:
338:
337:hybridization
334:
330:
326:
322:
318:
314:
310:
301:
299:
298:carbon-13 NMR
294:
292:
288:
284:
279:
277:
273:
269:
264:
247:
243:
220:
216:
206:
196:
192:
188:
184:
180:
175:
169:
161:
153:
141:
133:
121:
113:
109:
105:
101:
96:
94:
90:
86:
82:
78:
75:
71:
67:
63:
59:
55:
51:
44:
40:
36:
32:
29:
25:
21:
1793:
1686:
1683:J. Org. Chem
1682:
1676:
1643:
1639:
1632:
1615:
1598:
1579:
1571:the original
1561:
1553:
1549:
1544:
1508:
1497:
1482:
1473:
1464:
1455:
1448:
1444:
1437:
1431:
1421:
1416:
1412:
1408:
1404:
1400:
1399:Because the
1398:
1286:
1273:
1269:
1267:
1262:
1260:
1254:
1243:
1206:
1197:
1194:
1188:
1181:
1169:
1167:
1144:
1139:
1136:
1125:
1116:
1105:
1084:
1074:
1028:
1010:
467:
451:
422:
413:
345:
312:
307:
295:
280:
265:
207:
181:(TMS) as an
176:
97:
61:
57:
53:
49:
48:
23:
1403:th row has
1187:The 2.5 ppm
1180:The 2.5 ppm
1061:ethyl group
412:contribute
325:temperature
191:tetrahedral
79:within the
31:enantiomers
1889:Categories
1536:References
1419:+1 peaks.
1338:1 3 3 1
1276:th row of
373:atoms on C
108:Deuterated
74:hydrogen-1
54:proton NMR
1660:1523-7060
1493:satellite
1485:carbon-13
1055:- and -CH
479:crosspeak
444:deuterium
387:aliphatic
81:molecules
43:structure
1703:11671879
1668:16597139
1513:See also
1504:NMR tube
1346:quintet
1335:quartet
1327:1 2 1
1324:triplet
1313:doublet
1302:singlet
1257:protons.
464:methanol
406:olefinic
367:halogens
195:volatile
150:SO, and
132:methanol
100:solution
85:hydrogen
39:hydrogen
1787:Isotope
1780:isotope
1368:septet
1357:sextet
1263:quartet
1244:triplet
1204:group.
1198:triplet
1140:doublet
1117:singlet
1049:acetate
456:O shake
448:protium
321:solvent
287:benzene
120:acetone
104:solvent
89:isotope
28:menthol
1900:Proton
1701:
1666:
1658:
1606:
1591:
1390:nonet
1379:octet
1249:The CH
1238:The CH
1231:and CH
1160:The CH
1047:COO- (
890:NHCOR
460:Acidic
385:is an
154:, CDCl
102:, and
93:proton
77:nuclei
1624:(PDF)
1255:three
1170:twice
1149:-CH:
1128:hertz
1113:hertz
773:COOR
759:COOH
714:OCOCF
679:OCOR
442:, as
352:-OCOR
162:, CCl
142:, (CD
122:, (CD
62:H NMR
60:, or
1699:PMID
1664:PMID
1656:ISSN
1604:ISBN
1554:1991
1316:1 1
1294:Row
1291:Name
1063:(-CH
958:9.5
941:3.1
938:2.6
935:SOR
930:3.1
927:2.5
924:2.1
916:4.4
913:4.2
910:4.1
899:3.7
896:3.3
893:2.9
885:3.6
882:3.1
879:3.0
868:3.6
865:3.0
862:2.6
847:2.8
844:2.4
841:2.2
830:3.0
827:2.7
824:2.5
813:3.0
810:2.5
807:2.1
799:2.4
796:2.1
793:2.0
787:CONR
782:2.5
779:2.3
776:2.0
768:2.6
765:2.3
762:2.1
754:2.6
751:2.2
748:2.1
745:COR
740:2.5
737:2.4
734:2.2
731:CHO
723:4.4
720:4.0
709:5.1
706:4.2
703:3.9
693:OCOC
688:5.0
685:4.1
682:3.6
674:4.3
671:4.0
668:3.8
653:3.7
650:3.4
647:3.3
639:3.8
636:3.5
633:3.3
625:4.2
622:3.2
619:2.2
611:4.1
608:3.4
605:2.7
597:4.0
594:3.4
591:3.0
583:4.8
580:4.4
577:4.3
569:2.9
566:2.6
563:2.3
548:2.8
545:2.2
542:1.7
539:C≡C
534:2.6
531:2.0
528:1.6
525:C=C
520:1.6
517:1.3
514:0.8
365:and
170:, CS
138:OD,
134:, CD
1778:by
1691:doi
1648:doi
1432:ten
1219:-CH
1134:).
991:−15
989:to
972:10
921:SR
852:NRC
804:CN
644:OR
630:OH
602:Br
588:Cl
502:CH
432:-SH
425:-NH
381:. C
360:-NO
356:-OR
348:-OH
317:ppm
166:or
114:, D
68:in
1891::
1874:Pb
1869:Hg
1864:Pt
1859:Se
1854:Co
1849:Fe
1834:Si
1804:He
1697:.
1687:62
1685:.
1662:.
1654:.
1642:.
1305:1
1280::
1189:-
1182:+
1067:CH
987:−5
983:—
980:—
969:—
966:—
955:—
952:—
944:—
904:NO
873:NR
835:NR
818:NH
726:—
658:OC
616:I
574:F
511:R
507:CH
496:CH
490:CH
458:.
430:,
420:.
414:sp
404:,
400:.
358:,
354:,
350:,
327:,
323:,
293:.
56:,
1844:V
1839:P
1829:F
1824:O
1819:N
1814:C
1809:B
1799:H
1794:H
1768:e
1761:t
1754:v
1705:.
1693::
1670:.
1650::
1644:8
1626:.
1610:.
1556:.
1428:3
1426:)
1424:3
1417:n
1413:n
1409:n
1405:n
1401:n
1387:8
1376:7
1365:6
1354:5
1343:4
1332:3
1321:2
1310:1
1299:0
1287:n
1274:n
1270:n
1251:2
1240:3
1233:2
1229:3
1221:2
1217:3
1213:2
1209:n
1202:2
1174:2
1162:2
1155:2
1147:2
1100:2
1069:3
1065:2
1057:3
1053:2
1045:3
1041:H
1014:1
906:2
875:3
858:5
856:H
854:6
837:2
820:2
789:2
716:3
699:5
697:H
695:6
664:5
662:H
660:6
559:5
557:H
555:6
553:C
509:2
498:2
492:3
471:4
468:d
466:-
454:2
452:D
440:O
438:2
436:D
427:2
418:α
398:α
394:β
390:C
383:α
379:β
375:α
371:H
362:2
313:δ
248:0
244:B
221:0
217:B
203:3
199:3
172:2
164:4
156:3
148:2
146:)
144:3
136:3
128:2
126:)
124:3
116:2
52:(
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