1415:
398:
2190:
959:
47:
3660:
966:
973:
292:
1213:
1206:
1526:. In that case, the two isomers may as well be considered a single isomer, depending on the temperature and the context. For example, the two conformations of cyclohexane convert to each other quite rapidly at room temperature (in the liquid state), so that they are usually treated as a single isomer in chemistry.
1838:
a hydrocarbon that contains two overlapping double bonds. The double bonds are such that the three middle carbons are in a straight line, while the first three and last three lie on perpendicular planes. The molecule and its mirror image are not superimposable, even though the molecule has an axis of
2565:
Two parts of a molecule that are connected by just one single bond can rotate about that bond. While the bond itself is indifferent to that rotation, attractions and repulsions between the atoms in the two parts normally cause the energy of the whole molecule to vary (and possibly also the two parts
859:
The alcohol "3-propanol" is not another isomer, since the difference between it and 1-propanol is not real; it is only the result of an arbitrary choice in the direction of numbering the carbons along the chain. For the same reason, "ethoxymethane" is the same molecule as methoxyethane, not another
2985:
groups connected by a single bond â the repulsion between hydrogen atoms closest to the central single bond gives the fully planar conformation, with the two rings on the same plane, a higher energy than conformations where the two rings are skewed. In the gas phase, the molecule has therefore at
1877:
that passes through it. The rotation has the same magnitude but opposite senses for the two isomers, and can be a useful way of distinguishing and measuring their concentration in a solution. For this reason, enantiomers were formerly called "optical isomers". However, this term is ambiguous and is
5171:
L. Pasteur (1848) "MĂ©moire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire" (Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization),"
3592:
of the constituent atomic nuclei. This phenomenon is significant for molecular hydrogen, which can be partially separated into two long-lived states described as spin isomers or nuclear spin isomers: parahydrogen, with the spins of the two nuclei pointing in opposite directions, and orthohydrogen,
2664:
axis. Thus, even if those angles and distances are assumed fixed, there are infinitely many conformations for the ethane molecule, that differ by the relative angle Ï of rotation between the two groups. The feeble repulsion between the hydrogen atoms in the two methyl groups causes the energy to
1613:
Conversely, the energy barrier may be so high that the easiest way to overcome it would require temporarily breaking and then reforming one or more bonds of the molecule. In that case, the two isomers usually are stable enough to be isolated and treated as distinct substances. These isomers are
1713:
turns clockwise or counterclockwise as seen from the hydrogen atom. In order to change one conformation to the other, at some point those four atoms would have to lie on the same plane â which would require severely straining or breaking their bonds to the carbon atom. The corresponding energy
4159:
crystals came into two kinds of shapes that were mirror images of each other. Separating the crystals by hand, he obtained two version of tartaric acid, each of which would crystallize in only one of the two shapes, and rotated the plane of polarized light to the same degree but in opposite
2157:
on each carbon from switching places. Therefore, one has different configurational isomers depending on whether each hydroxyl is on "this side" or "the other side" of the ring's mean plane. Discounting isomers that are equivalent under rotations, there are nine isomers that differ by this
1303:
In theory, one can imagine any arrangement in space of the atoms of a molecule or ion to be gradually changed to any other arrangement in infinitely many ways, by moving each atom along an appropriate path. However, changes in the positions of atoms will generally change the internal
3607:
Isomerization is the process by which one molecule is transformed into another molecule that has exactly the same atoms, but the atoms are rearranged. In some molecules and under some conditions, isomerization occurs spontaneously. Many isomers are equal or roughly equal in
1626:) can significantly change the energy of conformations of a molecule. Therefore, the possible isomers of a compound in solution or in its liquid and solid phases many be very different from those of an isolated molecule in vacuum. Even in the gas phase, some compounds like
3095:
Different isotopes of the same element can be considered as different kinds of atoms when enumerating isomers of a molecule or ion. The replacement of one or more atoms by their isotopes can create multiple structural isomers and/or stereoisomers from a single isomer.
1319:; that is, an arrangement such that any small changes in the positions of the atoms will increase the internal energy, and hence result in forces that tend to push the atoms back to the original positions. Changing the shape of the molecule from such an energy minimum
1618:
or "configurations" of the molecule, not just two different conformations. (However, one should be aware that the terms "conformation" and "configuration" are largely synonymous outside of chemistry, and their distinction may be controversial even among chemists.)
2566:
to deform) depending on the relative angle of rotation Ï between the two parts. Then there will be one or more special values of Ï for which the energy is at a local minimum. The corresponding conformations of the molecule are called rotational isomers or
5087:Ăber die Zusammensetzung der WeinsĂ€ure und TraubensĂ€ure (John's sĂ€ure aus den Voghesen), ĂŒber das Atomengewicht des Bleioxyds, nebst allgemeinen Bemerkungen ĂŒber solche Körper, die gleiche Zusammensetzung, aber ungleiche Eigenschaften besitzen
1036:
Again, note that there is only one structural isomer with a triple bond, because the other possible placement of that bond is just drawing the three carbons in a different order. For the same reason, there is only one cyclopropene, not three.
4343:" ("On the composition of tartaric acid and racemic acid (John's acid of the Vosges), on the molecular weight of lead oxide, together with general observations on those bodies that have the same composition but distinct properties").
213:. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different
2350:
in coordination compounds) may give rise to multiple stereoisomers when different atoms or groups are attached at those positions. The same is true if a center with six or more equivalent bonds has two or more substituents.
2042:
recommended nomenclature. Conversion between these two forms usually requires temporarily breaking bonds (or turning the double bond into a single bond), so the two are considered different configurations of the molecule.
3635:
1903:) can be interconverted by internal motions that change bond lengths and angles only slightly. Other pairs (such as CHFClBr) cannot be interconverted without breaking bonds, and therefore are different configurations.
1418:
Molecular models of cyclohexane in boat and chair conformations. The carbon atoms are colored amber or blue according to whether they lie above or below the mean plane of the ring. The CâC bonds on the ring are light
4981:
Brown, K. N.; Field, L. D.; Lay, P. A.; Lindall, C. M.; Masters, A. F. (1990). "(η-Pentaphenylcyclopentadienyl){1-(η-phenyl)-2,3,4,5-tetraphenylcyclopentadienyl}iron(II), , a linkage isomer of decaphenylferrocene".
3044:
by such topological linkages, even if there is no chemical bond between them. If the molecules are large enough, the linking may occur in multiple topologically distinct ways, constituting different isomers.
1411:: the amount that must be temporarily added to the internal energy of the molecule in order to go through all the intermediate conformations along the "easiest" path (the one that minimizes that amount).
5104:
Composition de l'acide tartarique et de l'acide racĂ©mique (traubensĂ€ure); poids atomique de l'oxide de plomb, et remarques gĂ©nĂ©rals sur les corps qui ont la mĂȘme composition, et possĂšdent des proprietĂ©s
4341:
Om sammansÀttningen af vinsyra och drufsyra (John's sÀure aus den
Voghesen), om blyoxidens atomvigt, samt allmÀnna anmÀrkningar om sÄdana kroppar som hafva lika sammansÀttning, men skiljaktiga egenskaper
4703:
Takahiro
Iwamoto, Yoshiki Watanabe, Tatsuya Sadahiro, Takeharu Haino, and Shigeru Yamago (2011): "Size-selective encapsulation of C60 by cycloparaphenylene: Formation of the shortest fullerene-peapod".
1915:. If the two bonds on each carbon connect to different atoms, two distinct conformations are possible, that differ from each other by a twist of 180 degrees of one of the carbons about the double bond.
2022:
that has one chlorine bonded to each carbon. It has two conformational isomers, with the two chlorines on the same side or on opposite sides of the double bond's plane. They are traditionally called
1507:
angles must be far from that value (120 degrees for a regular hexagon). Thus the conformations which are local energy minima have the ring twisted in space, according to one of two patterns known as
3612:, and so exist in roughly equal amounts, provided that they can interconvert relatively freely, that is the energy barrier between the two isomers is not too high. When the isomerization occurs
4683:
A. T. H. Lenstra, C. Van
Alsenoy, K. Verhulst and H. J. Geise (1994): "Solids modelled by crystal field ab initio methods. 5. The phase transitions in biphenyl from a molecular point of view".
2057:(formerly called "geometric isomerism") occurs in molecules where the relative orientation of two distinguishable functional groups is restricted by a somewhat rigid framework of other atoms.
1161:
1646:
if their molecules are mirror images of each other, that cannot be made to coincide only by rotations or translations â like a left hand and a right hand. The two shapes are said to be
2401:. Thus two stereoisomers with that formula are possible, depending on whether the chlorine atom occupies one of the two "axial" positions, or one of the three "equatorial" positions.
1836:
1711:
3014:
of their overall arrangement in space, even if there is no specific geometric constraint that separate them. For example, long chains may be twisted to form topologically distinct
713:
854:
641:
1033:) the three carbons are connected into a ring by two single bonds and a double bond. In all three, the remaining valences of the carbon atoms are satisfied by the four hydrogens.
2806:
2020:
4062:
1714:
barrier between the two conformations is so high that there is practically no conversion between them at room temperature, and they can be regarded as different configurations.
3299:
3246:
1911:
A double bond between two carbon atoms forces the remaining four bonds (if they are single) to lie on the same plane, perpendicular to the plane of the bond as defined by its
2628:
2101:
1974:
1677:
3989:
3934:
3570:
3457:
3371:
3349:
2944:
2447:
1753:
3860:
3801:
3512:
2866:
2739:
2701:
2495:
2387:
2321:
2273:
1556:
1505:
1467:
1292:
Stereoisomers have the same atoms or isotopes connected by bonds of the same type, but differ in their shapes â the relative positions of those atoms in space â apart from
1272:
764:
485:
392:
3167:
3132:
2896:
1604:
949:
777:). Unlike the other two, it has the oxygen atom connected to two carbons, and all eight hydrogens bonded directly to carbons. It can be described by the condensed formula
2836:
2662:
2128:
536:
3889:
2155:
3422:
3400:
3189:
2547:
2525:
1405:
1383:
1361:
1339:
4138:
1469:
angles are close to 110 degrees. Conformations of the cyclohexane molecule with all six carbon atoms on the same plane have a higher energy, because some or all the
1221:
However, neither of these two structures describes a real compound; they are fictions devised as a way to describe (by their "averaging" or "resonance") the actual
397:
4160:
directions. In 1860, Pasteur explicitly hypothesized that the molecules of isomers might have the same composition but different arrangements of their atoms.
2178:
isomers can possibly have stable "chair" or "boat" conformations (although the barriers between these are significantly lower than those between different
5007:
Field, L. D.; Hambley, T. W.; Humphrey, P. A.; Lindall, C. M.; Gainsford, G. J.; Masters, A. F.; Stpierre, T. G.; Webb, J. (1995). "Decaphenylferrocene".
1534:
3765:(see structure above) is an important drug used in cancer chemotherapy, whereas the trans isomer (transplatin) has no useful pharmacological activity.
2977:
If the two parts of the molecule connected by a single bond are bulky or charged, the energy barriers may be much higher. For example, in the compound
4951:
4631:
4602:
4534:
1858:. For this latter reason, the two enantiomers of most chiral compounds usually have markedly different effects and roles in living organisms. In
1308:
of a molecule, which is determined by the angles between bonds in each atom and by the distances between atoms (whether they are bonded or not).
5150:
2502:
2213:
1844:
5035:
3811:
the previous year), its properties were distinct. This finding challenged the prevailing chemical understanding of the time, which held that
542:
atom bound to a hydrogen atom. These two isomers differ on which carbon the hydroxyl is bound to: either to an extremity of the carbon chain
3746:. Many preparative procedures afford a mixture of equal amounts of both enantiomeric forms. In some cases, the enantiomers are separated by
2986:
least two rotamers, with the ring planes twisted by ±47°, which are mirror images of each other. The barrier between them is rather low (~8
3195:
molecule yields two distinct structural isomers, depending on whether the substitutions are both on the same carbon (1,1-dideuteroethane,
4434:
4479:
3727:. It is used as an appetite-reducing medication and has mild or no stimulant properties. However, an alternate atomic arrangement gives
4462:
Rowena Ball and John
Brindley (2016): "The life story of hydrogen peroxide III: Chirality and physical effects at the dawn of life".
1512:
5187:"Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire"
2158:
criterion, and behave as different stable substances (two of them being enantiomers of each other). The most common one in nature (
4320:
3351:). While the original molecule is not chiral and has a single isomer, the substitution creates a pair of chiral enantiomers of
4300:
2998:. If the barrier is high enough for the two rotamers to be separated as stable compounds at room temperature, they are called
4869:
4523:
4372:
4265:
3376:
When two isomers would be identical if all isotopes of each element were replaced by a single isotope, they are described as
1850:
Enantiomers behave identically in chemical reactions, except when reacted with chiral compounds or in the presence of chiral
3082:, are a similar type of topological isomerism involving molecules with large internal voids with restricted or no openings.
5189:("On the relations that can exist between crystalline form, chemical composition, and the sense of rotary polarization"),
4406:
864:
1755:, in contrast, is not chiral: the mirror image of its molecule is also obtained by a half-turn about a suitable axis.
1508:
1053:
4733:
4495:
4450:
2902:
isomer where the two chlorines are on the same plane as the two carbons, but with oppositely directed bonds; and two
2335:
130:
111:
4842:"A study of spin isomer conversion kinetics in supercritical fluid hydrogen for cryogenic fuel storage technologies"
4518:
Whitten K.W., Gailey K.D. and Davis R.E. "General
Chemistry" (4th ed., Saunders College Publishing 1992), p. 976-7
2228:
1518:
If the energy barrier between two conformational isomers is low enough, it may be overcome by the random inputs of
83:
2741:
are 60° apart. Discounting rotations of the whole molecule, that configuration is a single isomer â the so-called
2162:-inositol) has the hydroxyls on carbons 1, 2, 3 and 5 on the same side of that plane, and can therefore be called
3305:
instead of deuterium. The two molecules do not interconvert easily and have different properties, such as their
3751:
1048:
are structural isomers which readily interconvert, so that two or more species co-exist in equilibrium such as
68:
3424:, the two dideuteroethanes would both become ethane and the two deuterochlorofluoromethanes would both become
2994:
effect is more pronounced when those four hydrogens are replaced by larger atoms or groups, like chlorines or
90:
3815:
could be distinct only when their elemental compositions differ. (We now know that the bonding structures of
2398:
2276:
3699:; but, if one of the two methyl groups is moved to a different position on the two-ring core, the isomer is
1764:
1682:
3634:
646:
217:. The depth of analysis depends on the field of study or the chemical and physical properties of interest.
2346:
More generally, atoms or atom groups that can form three or more non-equivalent single bonds (such as the
1634:
or larger groups of molecules, whose configurations may be different from those of the isolated molecule.
780:
572:
5234:
567:
2755:
1979:
97:
4724:
Eizi Hirota (2012): "Microwave spectroscopy of isotope-substituted non-polar molecules". Chapter 5 in
3998:
3755:
3251:
3033:). Some knots may come in mirror-image enantiomer pairs. Such forms are called topological isomers or
3198:
5122:
2808:
also has three local energy minima, but they have different energies due to differences between the
2580:
2066:
1921:
1660:
5064:
4891:
Chen, Judy Y.-C.; Li, Yongjun; Frunzi, Michael; Lei, Xuegong; Murata, Yasujiro; Lawler, Ronald G.;
4186:
3946:
3894:
3624:
3581:
3517:
3427:
3354:
3319:
2909:
2407:
1723:
1654:
79:
17:
3826:
3784:
3469:
2841:
2706:
2668:
2455:
2357:
2281:
2233:
2103:(a six-fold alcohol of cyclohexane), the six-carbon cyclic backbone largely prevents the hydroxyl
1539:
1472:
1434:
1232:
1001:
In two of the isomers, the three carbon atoms are connected in an open chain, but in one of them (
721:
442:
349:
4984:
4340:
3613:
3141:
3106:
2871:
2047:
1564:
909:
64:
57:
4141:
2811:
2637:
2106:
514:
499:. Both have a chain of three carbon atoms connected by single bonds, with the remaining carbon
4191:
3865:
3617:
3306:
2133:
1615:
1414:
1297:
1198:-xylene), which is often described as a mix of the two apparently distinct structural isomers:
35:
5186:
5103:
5086:
4431:
4362:
3405:
3383:
3172:
2665:
minimized for three specific values of Ï, 120° apart. In those configurations, the six planes
2530:
2508:
1388:
1366:
1344:
1322:
4476:
4176:
4067:
3728:
3720:
2224:
1312:
1187:
1167:
5134:
5048:
4908:
4853:
4768:
4221:
1622:
Interactions with other molecules of the same or different compounds (for example, through
1222:
189:
4663:
Kenneth B. Wiberg and Mark A. Murcko (1987): "Rotational barriers. 1. 1,2-Dihaloethanes".
2946:
groups are rotated about 109° from that position. The computed energy difference between
1533:
of the atoms themselves. This last phenomenon prevents the separation of stereoisomers of
8:
4181:
3939:
Additional examples were found in succeeding years, such as Wöhler's 1828 discovery that
3743:
3735:
3585:
3313:
2498:
1718:
1523:
1315:
is an arrangement of the atoms of the molecule or ion for which the internal energy is a
1293:
500:
492:
170:
5138:
5052:
4912:
4857:
4772:
3774:
3679:
Isomers having distinct biological properties are common; for example, the placement of
3312:
Another example would be substituting one atom of deuterium for one of the hydrogens in
2334:
labels are ambiguous. The IUPAC recommends a more precise labeling scheme, based on the
5229:
4934:
4758:
2749:
2449:, three isomers are possible, with zero, one, or two chlorines in the axial positions.
4443:
Conformational
Concept For Synthetic Chemist's Use: Principles And in Lab Exploitation
4317:
4926:
4897:"Nuclear spin isomers of guest molecules in H2@C60, H2O@C60 and other endofullerenes"
4786:
4729:
4519:
4491:
4446:
4368:
4279:
4271:
4261:
4254:
3812:
3808:
3708:
3628:
1897:
1631:
1559:
1530:
314:
305:
185:
181:
162:
4961:
4938:
4641:
4612:
4544:
4297:
3750:
using chiral stationary phases. They may also be separated through the formation of
3572:
are isotopologues and not isotopomers, and are therefore not isomers of each other.
104:
27:
Chemical compounds with the same molecular formula but different atomic arrangements
5142:
5056:
5016:
4989:
4965:
4956:
4916:
4861:
4820:
4776:
4709:
4688:
4668:
4645:
4636:
4616:
4607:
4548:
4539:
4396:
4206:
3992:
3804:
2991:
2347:
872:
258:
223:
4841:
1190:
between several apparently different structural isomers. The classical example is
30:
This article is about the chemical concept. For "isomerism" of atomic nuclei, see
4585:
4564:
4483:
4438:
4324:
4304:
3019:
1874:
1840:
1363:
will therefore require going through configurations that have higher energy than
1287:
251:
199:
5040:
4892:
4781:
4746:
4388:
4211:
3778:
3747:
3712:
3704:
3671:
are enzymes that can cut and reform circular DNA and thus change its topology.
3466:
or isotopic homologs, which differ in their isotopic composition. For example,
3373:, which could be distinguished (at least in theory) by their optical activity.
2630:, all the bond angles and length are narrowly constrained, except that the two
1519:
1408:
267:
247:
158:
31:
4825:
4808:
4692:
1679:). The two enantiomers can be distinguished, for example, by whether the path
1522:
that the molecule gets from interactions with the environment or from its own
5223:
4960:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4790:
4640:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4611:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4543:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4196:
4156:
4152:
3668:
3602:
3079:
3054:
3046:
1890:
1623:
1316:
770:
194:
4969:
4745:
Cameron, Robert P.; Götte, Jörg B.; Barnett, Stephen M. (8 September 2016).
4649:
4620:
4552:
4401:
4283:
2189:
4930:
4921:
4896:
4713:
4216:
3700:
3680:
3647:
3463:
1886:
1863:
1859:
1171:
1026:
346:
For example, there are three distinct compounds with the molecular formula
214:
1606:, because the two conformations with minimum energy interconvert in a few
1515:(with two opposite carbons above the plane, and the other four below it).
1407:. That is, a conformation isomer is separated from any other isomer by an
4993:
4500:
3724:
3716:
3692:
3688:
3651:
3609:
3015:
2999:
2198:
1839:
symmetry. The two enantiomers can be distinguished, for example, by the
1627:
1424:
1022:
1010:
904:
868:
559:
543:
4672:
2549:
bonds) are directed at the three corners of one face of the octahedron (
5146:
3739:
3377:
3034:
2390:
1759:
1643:
1607:
1175:
1002:
958:
5060:
5020:
4865:
4252:
Petrucci, Ralph H.; Harwood, William S.; Herring, F. Geoffrey (2002).
4260:(8th ed.). Upper Saddle River, N.J: Prentice Hall. p. 91].
4170:
3816:
3762:
3135:
2987:
2194:
1851:
1647:
283:
277:
271:
210:
146:
1912:
1873:
Each enantiomer of a chiral compound typically rotates the plane of
1870:â are usually identified, and treated as very different substances.
1511:(with the carbons alternately above and below their mean plane) and
46:
4763:
4584:
4563:
4226:
4201:
3696:
3684:
3302:
3100:
3041:
3011:
2995:
2978:
2061:
1191:
1045:
508:
504:
488:
154:
4275:
3659:
3627:
isomerization is the production of decaphenylferrocene, from its
2553:
isomer), or lie on the same equatorial or "meridian" plane of it (
965:
867:, which differ by the position at which certain features, such as
4231:
3820:
3030:
2567:
2394:
1867:
1428:
1275:
1014:
496:
202:
or (spatial isomerism), in which the bonds are the same but the
3192:
3050:
2982:
2967:
2631:
2574:
1855:
1305:
972:
539:
313:
have the same number of atoms of each element (hence the same
238:
4840:
Matthews, M.J.; Petitpas, G.; Aceves, S.M. (23 August 2011).
2039:
1879:
1212:
1205:
767:
235:
3040:
Also, two or more such molecules may be bound together in a
1186:
The structure of some molecules is sometimes described as a
291:
5006:
3940:
3781:
and discovered that, although its elemental composition of
229:
166:
3018:, with interconversion prevented by bulky substituents or
2954:
is ~1.5 kcal/mol, the barrier for the ~109° rotation from
4807:
Seeman, Jeffrey I.; Paine, III, J. B. (7 December 1992).
4039:
4018:
3974:
3961:
3580:
Another type of isomerism based on nuclear properties is
3558:
3545:
3532:
3497:
3484:
3442:
3334:
3287:
3266:
3234:
3213:
3027:
3023:
2929:
2791:
2770:
2616:
2595:
2483:
2470:
2435:
2422:
2372:
2309:
2296:
2261:
2248:
2089:
1962:
1949:
1936:
1824:
1779:
1738:
1592:
1579:
1260:
1247:
937:
924:
842:
816:
795:
749:
736:
701:
661:
626:
608:
587:
470:
457:
377:
364:
5123:"LiebigâWöhler Controversy and the Concept of Isomerism"
3742:
are a special concern because they may possess distinct
2962:
is ~5 kcal/mol, and that of the ~142° rotation from one
875:, occur on a "parent" molecule (propane, in that case).
4839:
4506:
4251:
3380:
or isotopic isomers. In the above two examples if all
1106:
4256:
General chemistry: principles and modern applications
4070:
4001:
3949:
3897:
3868:
3829:
3787:
3520:
3472:
3430:
3408:
3386:
3357:
3322:
3254:
3201:
3175:
3144:
3109:
2912:
2898:
interactions. There are therefore three rotamers: a
2874:
2844:
2814:
2758:
2709:
2671:
2640:
2583:
2533:
2511:
2458:
2410:
2360:
2284:
2236:
2136:
2109:
2069:
1982:
1924:
1866:, the two enantiomers of a chiral molecule â such as
1767:
1726:
1685:
1663:
1567:
1542:
1475:
1437:
1391:
1369:
1347:
1325:
1235:
1056:
912:
783:
724:
649:
575:
517:
445:
352:
232:
4980:
3010:
Large molecules may have isomers that differ by the
2966:
to its enantiomer is ~8 kcal/mol. The situation for
2906:
isomers, mirror images of each other, where the two
2341:
5036:"Fulminic Acid in the History of Organic Chemistry"
4744:
226:
177:refers to the existence or possibility of isomers.
71:. Unsourced material may be challenged and removed.
4809:"Letter to the Editor: 'Isotopomers, Isotopologs'"
4253:
4132:
4056:
3983:
3928:
3883:
3854:
3795:
3731:, which is a stronger stimulant than amphetamine.
3564:
3506:
3451:
3416:
3394:
3365:
3343:
3293:
3240:
3183:
3161:
3126:
2938:
2890:
2860:
2830:
2800:
2733:
2695:
2656:
2622:
2541:
2519:
2489:
2452:As another example, a complex with a formula like
2441:
2381:
2315:
2267:
2149:
2122:
2095:
2014:
1968:
1885:Stereoisomers that are not enantiomers are called
1830:
1747:
1705:
1671:
1598:
1550:
1499:
1461:
1399:
1377:
1355:
1333:
1278:core and two methyl groups in adjacent positions.
1266:
1155:
943:
848:
758:
707:
635:
530:
479:
386:
34:. For part of the body of the proarticulates, see
4901:Philosophical Transactions of the Royal Society A
4349:Transactions of the Royal Swedish Science Academy
1423:A classic example of conformational isomerism is
1156:{\displaystyle {\ce {H-X-Y=Z <=> X=Y-Z-H}}}
1114:
1113:
1096:
1095:
317:), but the atoms are connected in distinct ways.
5221:
5193:, 3rd series, volume 24, issue 6, pages 442â459.
5120:
4806:
2748:Rotation between the two halves of the molecule
2497:, where the central atom M forms six bonds with
173:â but distinct arrangements of atoms in space.
4890:
4345:Kongliga Svenska Vetenskaps Academiens Handling
4327:online dictionary entry. Accessed on 2020-08-26
4307:online dictionary entry. Accessed on 2020-08-26
903:There are also three structural isomers of the
3711:action. Another example of this occurs in the
3584:, where molecules differ only in the relative
3248:) or one on each carbon (1,2-dideuteroethane,
3593:where the spins point in the same direction.
3462:The concept of isotopomers is different from
1529:In some cases, the barrier can be crossed by
562:(2-propanol, isopropyl alcohol, isopropanol;
261:
3703:, which has a variety of effects, including
3650:proceeds via the cis-trans isomerization of
2560:
1021:) they are connected by a single bond and a
250:from "isomeric", which was borrowed through
4659:
4657:
4464:Origins of Life and Evolution of Biospheres
3773:Isomerism was first observed in 1827, when
3723:compound with a weaker effect than that of
3099:For example, replacing two atoms of common
2030:("on the other side of"), respectively; or
2026:(from Latin meaning "on this side of") and
4426:
4424:
4367:(1st ed.). McGraw-Hill. p. 450.
4335:
4333:
4310:
2634:groups can independently rotate about the
863:1-Propanol and 2-propanol are examples of
5174:Comptes rendus de l'Académie des sciences
5096:
5079:
5033:
4920:
4824:
4802:
4800:
4780:
4762:
4400:
4364:General, Organic and Biological Chemistry
2170:-4,6-cyclohexanehexol. And each of these
180:Isomers do not necessarily share similar
131:Learn how and when to remove this message
5205:The Atom in the History of Human Thought
4718:
4708:, volume 50, issue 36, pages 8342â8344.
4697:
4677:
4667:, volume 91, issue 13, pages 3616â3620.
4654:
4580:
4578:
4290:
3995:. (Their structures are now known to be
2326:For more complex organic molecules, the
2188:
1918:The classical example is dichloroethene
1896:Some enantiomer pairs (such as those of
1758:Another example of a chiral compound is
1413:
1229:-xylene, which is the single isomer of
1170:and the equilibrium between neutral and
290:
192:(or constitutional) isomerism, in which
4726:Molecular Spectroscopy: Modern Research
4706:Angewandte Chemie International Edition
4456:
4421:
4330:
1831:{\displaystyle {\ce {H3C-CH=C=CH-CH3}}}
1706:{\displaystyle {\ce {F->Cl->Br}}}
1431:generally have minimum energy when the
1089:
14:
5222:
4797:
4557:
3674:
1906:
708:{\displaystyle {\ce {H3C-CH(OH)-CH3}}}
4592:. Wiley Interscience. pp. 52â53.
4575:
4360:
1976:, specifically the structural isomer
849:{\displaystyle {\ce {H3C-CH2-O-CH3}}}
636:{\displaystyle {\ce {H3C-CH2-CH2OH}}}
299:
4590:Stereochemistry of Organic Compounds
4569:Stereochemistry of Organic Compounds
4507:Petrucci, Harwood & Herring 2002
3085:
69:adding citations to reliable sources
40:
5202:
5153:from the original on 23 August 2008
4571:. Wiley Interscience. p. 1203.
4469:
2970:is similar, but with sightly lower
2801:{\displaystyle {\ce {ClH2C-CH2Cl}}}
2338:for the bonds at each carbon atom.
2060:For example, in the cyclic alcohol
2015:{\displaystyle {\ce {Cl-HC=CH-Cl}}}
1843:. This type of isomerism is called
1009:) the carbons are connected by two
24:
4957:Compendium of Chemical Terminology
4637:Compendium of Chemical Terminology
4608:Compendium of Chemical Terminology
4540:Compendium of Chemical Terminology
4477:Methods of conformational analysis
4057:{\displaystyle {\ce {(H2N-)2C=O}}}
3823:can be approximately described as
3658:
3633:
2201:, are examples of square planar MX
1181:
396:
188:. Two main forms of isomerism are
25:
5246:
5215:
4409:from the original on 6 April 2019
3943:has the same atomic composition (
3695:with some effects in common with
3294:{\displaystyle {\ce {DH2C-CDH2}}}
2505:, depending on whether the three
2342:Centers with non-equivalent bonds
1889:. Some diastereomers may contain
1630:will exist mostly in the form of
566:). These can be described by the
320:
5191:Annales de Chimie et de Physique
5176:(Paris), vol. 26, pages 535â538.
5109:Annales de Chimie et de Physique
4819:(2). American Chemical Society.
4747:"Chiral rotational spectroscopy"
4685:Acta Crystallographica Section B
4475:Vallurupalli S. R. Rao (1998): "
4430:Anatoly M Belostotskii (2015): "
4361:Smith, Janice Gorzynski (2010).
3596:
3241:{\displaystyle {\ce {HD2C-CH3}}}
1281:
1211:
1204:
971:
964:
957:
878:
439:The first two isomers shown of
266:; which in turn was coined from
222:
45:
5196:
5179:
5165:
5114:
5027:
5000:
4974:
4945:
4884:
4872:from the original on 2 May 2022
4833:
4813:Chemical & Engineering News
4738:
4625:
4596:
4528:
4512:
3575:
2623:{\displaystyle {\ce {H3C-CH3}}}
2527:bonds (and thus also the three
2096:{\displaystyle {\ce {(CHOH)6}}}
1969:{\displaystyle {\ce {C2H2Cl2}}}
1672:{\displaystyle {\ce {CHFClBr}}}
1610:even at very low temperatures.
56:needs additional citations for
4381:
4354:
4245:
4125:
4096:
4091:
4073:
4029:
4005:
3984:{\displaystyle {\ce {CH4N2O}}}
3929:{\displaystyle {\ce {O=C=N-}}}
3565:{\displaystyle {\ce {C2H4D2}}}
3452:{\displaystyle {\ce {CH2ClF}}}
3366:{\displaystyle {\ce {CHDClF}}}
3344:{\displaystyle {\ce {CH2ClF}}}
3090:
3005:
2939:{\displaystyle {\ce {-CH2Cl}}}
2442:{\displaystyle {\ce {PF3Cl2}}}
2354:For instance, in the compound
2079:
2073:
1748:{\displaystyle {\ce {CH2ClF}}}
1696:
1690:
1637:
1116:
1091:
682:
676:
209:Isomeric relationships form a
198:between the atoms differ; and
165:â that is, the same number of
13:
1:
5091:Annalen der Physik und Chemie
4665:Journal of Physical Chemistry
4488:Conformation of Carbohydrates
4238:
3991:) as the chemically distinct
3855:{\displaystyle {\ce {O- N+}}}
3796:{\displaystyle {\ce {AgCNO}}}
3586:spin magnetic quantum numbers
3507:{\displaystyle {\ce {C2H5D}}}
3301:); as if the substituent was
2861:{\displaystyle {\ce {Cl-Cl}}}
2734:{\displaystyle {\ce {C-C-H}}}
2696:{\displaystyle {\ce {H-C-C}}}
2490:{\displaystyle {\ce {MX3Y3}}}
2399:trigonal bipyramidal geometry
2382:{\displaystyle {\ce {PF4Cl}}}
2316:{\displaystyle {\ce {MX4Y2}}}
2268:{\displaystyle {\ce {MX2Y2}}}
1642:Two compounds are said to be
1551:{\displaystyle {\ce {NHFCl}}}
1500:{\displaystyle {\ce {C-C-C}}}
1462:{\displaystyle {\ce {C-C-C}}}
1267:{\displaystyle {\ce {C8H10}}}
759:{\displaystyle {\ce {C3H8O}}}
568:condensed structural formulas
480:{\displaystyle {\ce {C3H8O}}}
387:{\displaystyle {\ce {C3H8O}}}
4985:J. Chem. Soc., Chem. Commun.
4687:, volume B50, pages 96-106.
4588:and Samuel H. Wilen (1994).
4567:and Samuel H. Wilen (1994).
4148:to describe the phenomenon.
3162:{\displaystyle {\ce {^2 H}}}
3127:{\displaystyle {\ce {^1 H}}}
2891:{\displaystyle {\ce {H-Cl}}}
2193:The two isomeric complexes,
1599:{\displaystyle {\ce {H2O2}}}
1040:
944:{\displaystyle {\ce {C3H4}}}
284:
278:
272:
7:
5111:, volume 46, pages 113â147.
4163:
3691:, found in chocolate, is a
2831:{\displaystyle {\ce {H-H}}}
2657:{\displaystyle {\ce {C-C}}}
2123:{\displaystyle {\ce {-OH}}}
531:{\displaystyle {\ce {-OH}}}
220:The English word "isomer" (
10:
5251:
5093:, volume 19, pages 305â335
4782:10.1103/physreva.94.032505
4432:Conformer and conformation
3884:{\displaystyle {\ce {C-}}}
3768:
3756:enantioselective synthesis
3600:
2150:{\displaystyle {\ce {-H}}}
1614:then said to be different
1341:to another energy minimum
1285:
558:) or to the middle carbon
303:
29:
5121:Esteban, Soledad (2008).
5102:J. J. Berzelius (1831): "
5085:J. J. Berzelius (1831): "
4826:10.1021/cen-v070n049.p002
4693:10.1107/S0108768193007931
4351:), volume 49, pages 49â80
4140:, respectively.) In 1830
3761:As an inorganic example,
3642:Synthesis of fumaric acid
3417:{\displaystyle {\ce {H}}}
3395:{\displaystyle {\ce {D}}}
3184:{\displaystyle {\ce {D}}}
3157:
3122:
2573:Thus, for example, in an
2561:Rotamers and atropisomers
2542:{\displaystyle {\ce {Y}}}
2520:{\displaystyle {\ce {X}}}
2503:facialâmeridional isomers
1400:{\displaystyle {\ce {B}}}
1378:{\displaystyle {\ce {A}}}
1356:{\displaystyle {\ce {B}}}
1334:{\displaystyle {\ce {A}}}
4466:, volume 46, pages 81â93
4339:Jac. Berzelius (1830): "
4187:Cyclohexane conformation
4133:{\displaystyle {\ce {}}}
3715:-based stimulant drugs.
3646:Industrial synthesis of
3152:
3146:
3117:
3111:
3022:closing (as in circular
2223:also occur in inorganic
1655:bromochlorofluoromethane
1025:. In the third isomer (
4970:10.1351/goldbook.I03295
4728:, volume 3. 466 pages.
4650:10.1351/goldbook.C01092
4621:10.1351/goldbook.G02620
4553:10.1351/goldbook.O04308
4402:10.1351/goldbook.T06252
4323:26 October 2020 at the
4303:21 October 2020 at the
2974:energies and barriers.
1653:A classical example is
1616:configurational isomers
1166:Important examples are
4922:10.1098/rsta.2011.0628
4714:10.1002/anie.201102302
4192:Descriptor (chemistry)
4134:
4058:
3985:
3930:
3885:
3856:
3797:
3663:
3638:
3618:rearrangement reaction
3566:
3508:
3453:
3418:
3396:
3367:
3345:
3295:
3242:
3185:
3163:
3128:
2940:
2892:
2862:
2832:
2802:
2735:
2697:
2658:
2624:
2543:
2521:
2491:
2443:
2383:
2317:
2269:
2225:coordination compounds
2210:
2209:molecules with M = Pt.
2151:
2124:
2097:
2016:
1970:
1832:
1749:
1707:
1673:
1600:
1552:
1501:
1463:
1420:
1401:
1379:
1357:
1335:
1268:
1157:
1013:, while in the other (
945:
850:
760:
709:
637:
532:
503:being filled by seven
481:
436:
401:Structural isomers of
388:
296:
262:
36:isomer (Proarticulata)
4895:(13 September 2013).
4482:18 April 2023 at the
4437:18 April 2023 at the
4177:Chirality (chemistry)
4135:
4059:
3986:
3931:
3886:
3857:
3798:
3758:have been developed.
3729:dextromethamphetamine
3662:
3637:
3616:, it is considered a
3567:
3509:
3454:
3419:
3397:
3368:
3346:
3296:
3243:
3186:
3164:
3129:
2941:
2893:
2863:
2833:
2803:
2736:
2698:
2659:
2625:
2544:
2522:
2492:
2444:
2389:, the bonds from the
2384:
2318:
2270:
2192:
2152:
2125:
2098:
2017:
1971:
1833:
1750:
1708:
1674:
1601:
1553:
1502:
1464:
1417:
1402:
1380:
1358:
1336:
1313:conformational isomer
1269:
1168:keto-enol tautomerism
1158:
946:
851:
773:(ethyl-methyl-ether;
761:
710:
638:
533:
482:
400:
389:
294:
206:of the atoms differ.
4994:10.1039/C39900000408
4222:Structural isomerism
4144:introduced the term
4142:Jöns Jacob Berzelius
4068:
3999:
3947:
3895:
3866:
3827:
3785:
3752:diastereomeric salts
3518:
3470:
3428:
3406:
3384:
3355:
3320:
3252:
3199:
3173:
3142:
3107:
2910:
2872:
2842:
2812:
2756:
2707:
2669:
2638:
2581:
2531:
2509:
2456:
2408:
2358:
2282:
2234:
2134:
2107:
2067:
1980:
1922:
1765:
1724:
1683:
1661:
1565:
1540:
1473:
1435:
1389:
1367:
1345:
1323:
1233:
1054:
1017:or methylacetylene;
910:
781:
722:
718:The third isomer of
647:
573:
515:
443:
350:
65:improve this article
5139:2008JChEd..85.1201E
5067:on 18 February 2009
5053:2000JChEd..77..851K
4913:2013RSPTA.37110628C
4858:2011ApPhL..99h1906M
4773:2016PhRvA..94c2505C
4673:10.1021/j100297a030
4613:geometric isomerism
4509:, pp. 996â997.
4182:Cis-trans isomerism
4090:
4041:
4020:
3976:
3963:
3744:biological activity
3736:medicinal chemistry
3675:Medicinal chemistry
3560:
3547:
3534:
3499:
3486:
3444:
3336:
3314:chlorofluoromethane
3289:
3268:
3236:
3215:
2931:
2793:
2772:
2618:
2597:
2501:, has at least two
2499:octahedral geometry
2485:
2472:
2437:
2424:
2397:have approximately
2374:
2311:
2298:
2263:
2250:
2091:
1964:
1951:
1938:
1907:Cis-trans isomerism
1878:discouraged by the
1826:
1781:
1740:
1719:chlorofluoromethane
1594:
1581:
1262:
1249:
1223:delocalized bonding
1192:1,2-dimethylbenzene
1102:
939:
926:
844:
818:
797:
751:
738:
703:
663:
628:
610:
589:
472:
459:
435:ethyl-methyl-ether.
379:
366:
186:physical properties
5235:1827 introductions
5185:L. Pasteur (1848)
5147:10.1021/ed085p1201
5034:F. Kurzer (2000).
4130:
4076:
4054:
4008:
4003:
3981:
3964:
3951:
3926:
3881:
3852:
3813:chemical compounds
3793:
3754:. In other cases,
3738:and biochemistry,
3664:
3639:
3562:
3548:
3535:
3522:
3504:
3487:
3474:
3449:
3432:
3414:
3392:
3363:
3341:
3324:
3307:microwave spectrum
3291:
3277:
3256:
3238:
3224:
3203:
3181:
3159:
3124:
2936:
2919:
2888:
2858:
2828:
2798:
2781:
2760:
2750:1,2-dichloroethane
2731:
2693:
2654:
2620:
2606:
2585:
2539:
2517:
2487:
2473:
2460:
2439:
2425:
2412:
2379:
2362:
2313:
2299:
2286:
2265:
2251:
2238:
2211:
2147:
2120:
2093:
2071:
2012:
1966:
1952:
1939:
1926:
1828:
1814:
1769:
1745:
1728:
1703:
1669:
1596:
1582:
1569:
1548:
1497:
1459:
1421:
1397:
1375:
1353:
1331:
1264:
1250:
1237:
1153:
1121:
941:
927:
914:
865:positional isomers
846:
832:
806:
785:
756:
739:
726:
705:
691:
651:
633:
616:
598:
577:
528:
477:
460:
447:
437:
384:
367:
354:
311:Structural isomers
300:Structural isomers
297:
204:relative positions
5061:10.1021/ed077p851
5021:10.1071/CH9950851
4866:10.1063/1.3628453
4751:Physical Review A
4524:978-0-03-072373-5
4374:978-0-07-302657-2
4316:Merriam-Webster:
4296:Merriam-Webster:
4267:978-0-13-014329-7
4118:
4109:
4101:
4079:
4052:
4044:
4023:
4011:
3979:
3967:
3954:
3936:, respectively.)
3918:
3909:
3901:
3873:
3844:
3834:
3809:Justus von Liebig
3803:was identical to
3791:
3709:anti-inflammatory
3683:. In substituted
3623:An example of an
3551:
3538:
3525:
3502:
3490:
3477:
3447:
3435:
3412:
3402:were replaced by
3390:
3361:
3339:
3327:
3280:
3271:
3259:
3227:
3218:
3206:
3179:
3153:
3151:
3150:
3149:
3118:
3116:
3115:
3114:
3086:Isotopes and spin
2934:
2922:
2886:
2878:
2856:
2848:
2826:
2818:
2796:
2784:
2775:
2763:
2729:
2721:
2713:
2691:
2683:
2675:
2652:
2644:
2609:
2600:
2588:
2537:
2515:
2476:
2463:
2428:
2415:
2404:For the compound
2393:atom to the five
2377:
2365:
2348:transition metals
2302:
2289:
2254:
2241:
2145:
2130:and the hydrogen
2118:
2078:
2010:
2002:
1994:
1986:
1955:
1942:
1929:
1817:
1808:
1800:
1792:
1784:
1772:
1743:
1731:
1701:
1695:
1689:
1667:
1585:
1572:
1560:hydrogen peroxide
1546:
1535:fluorochloroamine
1531:quantum tunneling
1495:
1487:
1479:
1457:
1449:
1441:
1395:
1373:
1351:
1329:
1253:
1240:
1219:
1218:
1151:
1143:
1135:
1127:
1123:
1084:
1076:
1068:
1060:
999:
998:
930:
917:
873:functional groups
835:
826:
809:
800:
788:
754:
742:
729:
694:
681:
674:
666:
654:
631:
619:
601:
592:
580:
550:-propyl alcohol,
526:
475:
463:
450:
382:
370:
357:
315:molecular formula
306:Structural isomer
163:molecular formula
141:
140:
133:
115:
16:(Redirected from
5242:
5209:
5203:Pullman (1998).
5200:
5194:
5183:
5177:
5169:
5163:
5162:
5160:
5158:
5118:
5112:
5100:
5094:
5083:
5077:
5076:
5074:
5072:
5063:. Archived from
5031:
5025:
5024:
5004:
4998:
4997:
4978:
4972:
4949:
4943:
4942:
4924:
4888:
4882:
4881:
4879:
4877:
4846:Appl. Phys. Lett
4837:
4831:
4830:
4828:
4804:
4795:
4794:
4784:
4766:
4742:
4736:
4722:
4716:
4701:
4695:
4681:
4675:
4661:
4652:
4629:
4623:
4600:
4594:
4593:
4582:
4573:
4572:
4561:
4555:
4532:
4526:
4516:
4510:
4504:
4498:
4486:". Chapter 2 in
4473:
4467:
4460:
4454:
4441:", chapter 2 of
4428:
4419:
4418:
4416:
4414:
4404:
4385:
4379:
4378:
4358:
4352:
4337:
4328:
4314:
4308:
4294:
4288:
4287:
4259:
4249:
4207:Ligand isomerism
4202:Isomery (botany)
4139:
4137:
4136:
4131:
4129:
4128:
4124:
4123:
4116:
4114:
4107:
4106:
4099:
4094:
4089:
4084:
4077:
4063:
4061:
4060:
4055:
4053:
4050:
4049:
4042:
4040:
4037:
4032:
4028:
4021:
4019:
4016:
4009:
3993:ammonium cyanate
3990:
3988:
3987:
3982:
3980:
3977:
3975:
3972:
3965:
3962:
3959:
3952:
3935:
3933:
3932:
3927:
3925:
3924:
3923:
3916:
3914:
3907:
3906:
3899:
3890:
3888:
3887:
3882:
3880:
3879:
3878:
3871:
3861:
3859:
3858:
3853:
3851:
3850:
3849:
3842:
3840:
3839:
3832:
3805:silver fulminate
3802:
3800:
3799:
3794:
3792:
3789:
3775:Friedrich Wöhler
3614:intramolecularly
3571:
3569:
3568:
3563:
3561:
3559:
3556:
3549:
3546:
3543:
3536:
3533:
3530:
3523:
3513:
3511:
3510:
3505:
3503:
3500:
3498:
3495:
3488:
3485:
3482:
3475:
3458:
3456:
3455:
3450:
3448:
3445:
3443:
3440:
3433:
3423:
3421:
3420:
3415:
3413:
3410:
3401:
3399:
3398:
3393:
3391:
3388:
3372:
3370:
3369:
3364:
3362:
3359:
3350:
3348:
3347:
3342:
3340:
3337:
3335:
3332:
3325:
3300:
3298:
3297:
3292:
3290:
3288:
3285:
3278:
3276:
3269:
3267:
3264:
3257:
3247:
3245:
3244:
3239:
3237:
3235:
3232:
3225:
3223:
3216:
3214:
3211:
3204:
3190:
3188:
3187:
3182:
3180:
3177:
3168:
3166:
3165:
3160:
3158:
3147:
3133:
3131:
3130:
3125:
3123:
3112:
3077:
3076:
3075:
3067:
3066:
2992:steric hindrance
2945:
2943:
2942:
2937:
2935:
2932:
2930:
2927:
2920:
2918:
2897:
2895:
2894:
2889:
2887:
2884:
2883:
2876:
2867:
2865:
2864:
2859:
2857:
2854:
2853:
2846:
2837:
2835:
2834:
2829:
2827:
2824:
2823:
2816:
2807:
2805:
2804:
2799:
2797:
2794:
2792:
2789:
2782:
2780:
2773:
2771:
2768:
2761:
2740:
2738:
2737:
2732:
2730:
2727:
2726:
2719:
2718:
2711:
2702:
2700:
2699:
2694:
2692:
2689:
2688:
2681:
2680:
2673:
2663:
2661:
2660:
2655:
2653:
2650:
2649:
2642:
2629:
2627:
2626:
2621:
2619:
2617:
2614:
2607:
2605:
2598:
2596:
2593:
2586:
2548:
2546:
2545:
2540:
2538:
2535:
2526:
2524:
2523:
2518:
2516:
2513:
2496:
2494:
2493:
2488:
2486:
2484:
2481:
2474:
2471:
2468:
2461:
2448:
2446:
2445:
2440:
2438:
2436:
2433:
2426:
2423:
2420:
2413:
2388:
2386:
2385:
2380:
2378:
2375:
2373:
2370:
2363:
2322:
2320:
2319:
2314:
2312:
2310:
2307:
2300:
2297:
2294:
2287:
2274:
2272:
2271:
2266:
2264:
2262:
2259:
2252:
2249:
2246:
2239:
2156:
2154:
2153:
2148:
2146:
2143:
2142:
2129:
2127:
2126:
2121:
2119:
2116:
2115:
2102:
2100:
2099:
2094:
2092:
2090:
2087:
2082:
2076:
2046:More generally,
2021:
2019:
2018:
2013:
2011:
2008:
2007:
2000:
1999:
1992:
1991:
1984:
1975:
1973:
1972:
1967:
1965:
1963:
1960:
1953:
1950:
1947:
1940:
1937:
1934:
1927:
1837:
1835:
1834:
1829:
1827:
1825:
1822:
1815:
1813:
1806:
1805:
1798:
1797:
1790:
1789:
1782:
1780:
1777:
1770:
1754:
1752:
1751:
1746:
1744:
1741:
1739:
1736:
1729:
1712:
1710:
1709:
1704:
1702:
1699:
1693:
1687:
1678:
1676:
1675:
1670:
1668:
1665:
1605:
1603:
1602:
1597:
1595:
1593:
1590:
1583:
1580:
1577:
1570:
1557:
1555:
1554:
1549:
1547:
1544:
1506:
1504:
1503:
1498:
1496:
1493:
1492:
1485:
1484:
1477:
1468:
1466:
1465:
1460:
1458:
1455:
1454:
1447:
1446:
1439:
1406:
1404:
1403:
1398:
1396:
1393:
1384:
1382:
1381:
1376:
1374:
1371:
1362:
1360:
1359:
1354:
1352:
1349:
1340:
1338:
1337:
1332:
1330:
1327:
1273:
1271:
1270:
1265:
1263:
1261:
1258:
1251:
1248:
1245:
1238:
1215:
1208:
1201:
1200:
1162:
1160:
1159:
1154:
1152:
1149:
1148:
1141:
1140:
1133:
1132:
1125:
1124:
1122:
1120:
1119:
1112:
1104:
1103:
1101:
1094:
1086:
1082:
1081:
1074:
1073:
1066:
1065:
1058:
975:
968:
961:
954:
953:
950:
948:
947:
942:
940:
938:
935:
928:
925:
922:
915:
899:
898:
897:
889:
888:
855:
853:
852:
847:
845:
843:
840:
833:
831:
824:
823:
817:
814:
807:
805:
798:
796:
793:
786:
765:
763:
762:
757:
755:
752:
750:
747:
740:
737:
734:
727:
714:
712:
711:
706:
704:
702:
699:
692:
690:
685:
679:
672:
671:
664:
662:
659:
652:
642:
640:
639:
634:
632:
629:
627:
624:
617:
615:
609:
606:
599:
597:
590:
588:
585:
578:
537:
535:
534:
529:
527:
524:
523:
486:
484:
483:
478:
476:
473:
471:
468:
461:
458:
455:
448:
422:
420:
419:
411:
410:
393:
391:
390:
385:
383:
380:
378:
375:
368:
365:
362:
355:
342:
340:
339:
331:
330:
295:Types of isomers
287:
281:
275:
265:
245:
244:
241:
240:
237:
234:
231:
228:
136:
129:
125:
122:
116:
114:
73:
49:
41:
21:
5250:
5249:
5245:
5244:
5243:
5241:
5240:
5239:
5220:
5219:
5218:
5213:
5212:
5201:
5197:
5184:
5180:
5170:
5166:
5156:
5154:
5119:
5115:
5101:
5097:
5084:
5080:
5070:
5068:
5032:
5028:
5005:
5001:
4979:
4975:
4950:
4946:
4893:Turro, Nicholas
4889:
4885:
4875:
4873:
4838:
4834:
4805:
4798:
4743:
4739:
4723:
4719:
4702:
4698:
4682:
4678:
4662:
4655:
4630:
4626:
4601:
4597:
4586:Ernest L. Eliel
4583:
4576:
4565:Ernest L. Eliel
4562:
4558:
4545:optical isomers
4533:
4529:
4517:
4513:
4505:
4501:
4484:Wayback Machine
4474:
4470:
4461:
4457:
4439:Wayback Machine
4429:
4422:
4412:
4410:
4395:. IUPAC. 2014.
4393:IUPAC Gold Book
4387:
4386:
4382:
4375:
4359:
4355:
4338:
4331:
4325:Wayback Machine
4315:
4311:
4305:Wayback Machine
4295:
4291:
4268:
4250:
4246:
4241:
4236:
4166:
4119:
4115:
4110:
4102:
4095:
4085:
4080:
4072:
4071:
4069:
4066:
4065:
4045:
4038:
4033:
4024:
4017:
4012:
4004:
4002:
4000:
3997:
3996:
3973:
3968:
3960:
3955:
3950:
3948:
3945:
3944:
3919:
3915:
3910:
3902:
3898:
3896:
3893:
3892:
3874:
3870:
3869:
3867:
3864:
3863:
3845:
3841:
3835:
3831:
3830:
3828:
3825:
3824:
3788:
3786:
3783:
3782:
3771:
3705:bronchodilation
3677:
3605:
3599:
3591:
3578:
3557:
3552:
3544:
3539:
3531:
3526:
3521:
3519:
3516:
3515:
3496:
3491:
3483:
3478:
3473:
3471:
3468:
3467:
3441:
3436:
3431:
3429:
3426:
3425:
3409:
3407:
3404:
3403:
3387:
3385:
3382:
3381:
3358:
3356:
3353:
3352:
3333:
3328:
3323:
3321:
3318:
3317:
3286:
3281:
3272:
3265:
3260:
3255:
3253:
3250:
3249:
3233:
3228:
3219:
3212:
3207:
3202:
3200:
3197:
3196:
3176:
3174:
3171:
3170:
3145:
3143:
3140:
3139:
3110:
3108:
3105:
3104:
3093:
3088:
3074:
3071:
3070:
3069:
3065:
3062:
3061:
3060:
3058:
3008:
2928:
2923:
2914:
2913:
2911:
2908:
2907:
2879:
2875:
2873:
2870:
2869:
2849:
2845:
2843:
2840:
2839:
2819:
2815:
2813:
2810:
2809:
2790:
2785:
2776:
2769:
2764:
2759:
2757:
2754:
2753:
2722:
2714:
2710:
2708:
2705:
2704:
2684:
2676:
2672:
2670:
2667:
2666:
2645:
2641:
2639:
2636:
2635:
2615:
2610:
2601:
2594:
2589:
2584:
2582:
2579:
2578:
2563:
2534:
2532:
2529:
2528:
2512:
2510:
2507:
2506:
2482:
2477:
2469:
2464:
2459:
2457:
2454:
2453:
2434:
2429:
2421:
2416:
2411:
2409:
2406:
2405:
2371:
2366:
2361:
2359:
2356:
2355:
2344:
2308:
2303:
2295:
2290:
2285:
2283:
2280:
2279:
2260:
2255:
2247:
2242:
2237:
2235:
2232:
2231:
2208:
2204:
2138:
2137:
2135:
2132:
2131:
2111:
2110:
2108:
2105:
2104:
2088:
2083:
2072:
2070:
2068:
2065:
2064:
2003:
1995:
1987:
1983:
1981:
1978:
1977:
1961:
1956:
1948:
1943:
1935:
1930:
1925:
1923:
1920:
1919:
1909:
1875:polarized light
1854:, such as most
1845:axial isomerism
1841:right-hand rule
1823:
1818:
1809:
1801:
1793:
1785:
1778:
1773:
1768:
1766:
1763:
1762:
1737:
1732:
1727:
1725:
1722:
1721:
1686:
1684:
1681:
1680:
1664:
1662:
1659:
1658:
1640:
1591:
1586:
1578:
1573:
1568:
1566:
1563:
1562:
1543:
1541:
1538:
1537:
1488:
1480:
1476:
1474:
1471:
1470:
1450:
1442:
1438:
1436:
1433:
1432:
1392:
1390:
1387:
1386:
1370:
1368:
1365:
1364:
1348:
1346:
1343:
1342:
1326:
1324:
1321:
1320:
1290:
1288:Stereoisomerism
1284:
1259:
1254:
1246:
1241:
1236:
1234:
1231:
1230:
1184:
1182:Resonance forms
1144:
1136:
1128:
1115:
1108:
1107:
1105:
1097:
1090:
1088:
1087:
1085:
1077:
1069:
1061:
1057:
1055:
1052:
1051:
1043:
936:
931:
923:
918:
913:
911:
908:
907:
901:
896:
893:
892:
891:
887:
884:
883:
882:
880:
841:
836:
827:
819:
815:
810:
801:
794:
789:
784:
782:
779:
778:
748:
743:
735:
730:
725:
723:
720:
719:
700:
695:
686:
675:
667:
660:
655:
650:
648:
645:
644:
625:
620:
611:
607:
602:
593:
586:
581:
576:
574:
571:
570:
538:comprising the
519:
518:
516:
513:
512:
507:atoms and by a
469:
464:
456:
451:
446:
444:
441:
440:
418:
415:
414:
413:
409:
406:
405:
404:
402:
376:
371:
363:
358:
353:
351:
348:
347:
344:
338:
335:
334:
333:
329:
326:
325:
324:
322:
308:
302:
225:
221:
200:stereoisomerism
161:with identical
159:polyatomic ions
137:
126:
120:
117:
74:
72:
62:
50:
39:
28:
23:
22:
15:
12:
11:
5:
5248:
5238:
5237:
5232:
5217:
5216:External links
5214:
5211:
5210:
5195:
5178:
5164:
5113:
5095:
5078:
5047:(7): 851â857.
5041:J. Chem. Educ.
5026:
5015:(4): 851â860.
4999:
4988:(5): 408â410.
4973:
4944:
4883:
4832:
4796:
4737:
4717:
4696:
4676:
4653:
4624:
4595:
4574:
4556:
4527:
4511:
4499:
4468:
4455:
4420:
4380:
4373:
4353:
4329:
4309:
4289:
4266:
4243:
4242:
4240:
4237:
4235:
4234:
4229:
4224:
4219:
4214:
4212:Nuclear isomer
4209:
4204:
4199:
4194:
4189:
4184:
4179:
4174:
4167:
4165:
4162:
4155:observed that
4127:
4122:
4113:
4105:
4098:
4093:
4088:
4083:
4075:
4048:
4036:
4031:
4027:
4015:
4007:
3971:
3958:
3922:
3913:
3905:
3877:
3848:
3838:
3779:silver cyanate
3770:
3767:
3748:chromatography
3713:phenethylamine
3676:
3673:
3669:Topoisomerases
3666:
3665:
3644:
3643:
3629:linkage isomer
3625:organometallic
3601:Main article:
3598:
3595:
3589:
3582:spin isomerism
3577:
3574:
3555:
3542:
3529:
3494:
3481:
3439:
3331:
3284:
3275:
3263:
3231:
3222:
3210:
3156:
3121:
3092:
3089:
3087:
3084:
3080:carbon peapods
3072:
3063:
3047:Cage compounds
3007:
3004:
2926:
2917:
2882:
2852:
2822:
2788:
2779:
2767:
2745:conformation.
2725:
2717:
2687:
2679:
2648:
2613:
2604:
2592:
2562:
2559:
2480:
2467:
2432:
2419:
2369:
2343:
2340:
2336:CIP priorities
2306:
2293:
2275:complexes and
2258:
2245:
2206:
2202:
2141:
2114:
2086:
2081:
2075:
2006:
1998:
1990:
1959:
1946:
1933:
1908:
1905:
1821:
1812:
1804:
1796:
1788:
1776:
1760:2,3-pentadiene
1735:
1698:
1692:
1639:
1636:
1624:hydrogen bonds
1589:
1576:
1520:thermal energy
1491:
1483:
1453:
1445:
1409:energy barrier
1286:Main article:
1283:
1280:
1257:
1244:
1217:
1216:
1209:
1183:
1180:
1147:
1139:
1131:
1118:
1111:
1100:
1093:
1080:
1072:
1064:
1042:
1039:
997:
996:
990:
984:
977:
976:
969:
962:
934:
921:
900:
894:
885:
877:
839:
830:
822:
813:
804:
792:
746:
733:
698:
689:
684:
678:
670:
658:
623:
614:
605:
596:
584:
522:
467:
454:
416:
407:
374:
361:
343:
336:
327:
319:
304:Main article:
301:
298:
248:back-formation
139:
138:
121:September 2021
53:
51:
44:
32:nuclear isomer
26:
9:
6:
4:
3:
2:
5247:
5236:
5233:
5231:
5228:
5227:
5225:
5208:
5206:
5199:
5192:
5188:
5182:
5175:
5168:
5152:
5148:
5144:
5140:
5136:
5132:
5128:
5127:J. Chem. Educ
5124:
5117:
5110:
5106:
5099:
5092:
5088:
5082:
5066:
5062:
5058:
5054:
5050:
5046:
5043:
5042:
5037:
5030:
5022:
5018:
5014:
5010:
5009:Aust. J. Chem
5003:
4995:
4991:
4987:
4986:
4977:
4971:
4967:
4963:
4962:isomerization
4959:
4958:
4953:
4948:
4940:
4936:
4932:
4928:
4923:
4918:
4914:
4910:
4906:
4902:
4898:
4894:
4887:
4871:
4867:
4863:
4859:
4855:
4852:(8): 081906.
4851:
4847:
4843:
4836:
4827:
4822:
4818:
4814:
4810:
4803:
4801:
4792:
4788:
4783:
4778:
4774:
4770:
4765:
4760:
4757:(3): 032505.
4756:
4752:
4748:
4741:
4735:
4734:9780323149327
4731:
4727:
4721:
4715:
4711:
4707:
4700:
4694:
4690:
4686:
4680:
4674:
4670:
4666:
4660:
4658:
4651:
4647:
4643:
4639:
4638:
4633:
4628:
4622:
4618:
4614:
4610:
4609:
4604:
4599:
4591:
4587:
4581:
4579:
4570:
4566:
4560:
4554:
4550:
4546:
4542:
4541:
4536:
4531:
4525:
4521:
4515:
4508:
4503:
4497:
4496:9789057023156
4493:
4490:. 409 pages.
4489:
4485:
4481:
4478:
4472:
4465:
4459:
4452:
4451:9789814730235
4448:
4445:. 580 pages.
4444:
4440:
4436:
4433:
4427:
4425:
4408:
4403:
4398:
4394:
4390:
4389:"tautomerism"
4384:
4376:
4370:
4366:
4365:
4357:
4350:
4346:
4342:
4336:
4334:
4326:
4322:
4319:
4313:
4306:
4302:
4299:
4293:
4285:
4281:
4277:
4273:
4269:
4263:
4258:
4257:
4248:
4244:
4233:
4230:
4228:
4225:
4223:
4220:
4218:
4215:
4213:
4210:
4208:
4205:
4203:
4200:
4198:
4197:Electromerism
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4175:
4173:(of elements)
4172:
4169:
4168:
4161:
4158:
4157:tartaric acid
4154:
4153:Louis Pasteur
4149:
4147:
4143:
4120:
4111:
4103:
4086:
4081:
4046:
4034:
4025:
4013:
3994:
3969:
3956:
3942:
3937:
3920:
3911:
3903:
3875:
3846:
3836:
3822:
3818:
3814:
3810:
3807:(prepared by
3806:
3780:
3776:
3766:
3764:
3759:
3757:
3753:
3749:
3745:
3741:
3737:
3732:
3730:
3726:
3722:
3718:
3714:
3710:
3706:
3702:
3698:
3694:
3690:
3686:
3682:
3681:methyl groups
3672:
3670:
3661:
3657:
3656:
3655:
3653:
3649:
3641:
3640:
3636:
3632:
3630:
3626:
3621:
3619:
3615:
3611:
3604:
3603:Isomerization
3597:Isomerization
3594:
3587:
3583:
3573:
3553:
3540:
3527:
3492:
3479:
3465:
3460:
3437:
3379:
3374:
3329:
3315:
3310:
3308:
3304:
3282:
3273:
3261:
3229:
3220:
3208:
3194:
3154:
3137:
3119:
3102:
3097:
3083:
3081:
3056:
3055:dodecahedrane
3052:
3048:
3043:
3038:
3036:
3032:
3029:
3025:
3021:
3017:
3013:
3003:
3001:
2997:
2993:
2989:
2984:
2980:
2975:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2924:
2915:
2905:
2901:
2880:
2850:
2820:
2786:
2777:
2765:
2751:
2746:
2744:
2723:
2715:
2685:
2677:
2646:
2633:
2611:
2602:
2590:
2576:
2571:
2569:
2558:
2556:
2552:
2504:
2500:
2478:
2465:
2450:
2430:
2417:
2402:
2400:
2396:
2392:
2367:
2352:
2349:
2339:
2337:
2333:
2329:
2324:
2304:
2291:
2278:
2256:
2243:
2230:
2229:square planar
2226:
2222:
2220:
2216:
2200:
2196:
2191:
2187:
2185:
2181:
2177:
2173:
2169:
2165:
2161:
2139:
2112:
2084:
2063:
2058:
2056:
2054:
2050:
2044:
2041:
2037:
2033:
2029:
2025:
2004:
1996:
1988:
1957:
1944:
1931:
1916:
1914:
1904:
1902:
1900:
1894:
1892:
1891:chiral center
1888:
1887:diastereomers
1883:
1881:
1876:
1871:
1869:
1865:
1861:
1857:
1853:
1848:
1846:
1842:
1819:
1810:
1802:
1794:
1786:
1774:
1761:
1756:
1733:
1720:
1717:The compound
1715:
1656:
1651:
1649:
1645:
1635:
1633:
1629:
1625:
1620:
1617:
1611:
1609:
1587:
1574:
1561:
1536:
1532:
1527:
1525:
1521:
1516:
1514:
1510:
1489:
1481:
1451:
1443:
1430:
1426:
1416:
1412:
1410:
1318:
1317:local minimum
1314:
1309:
1307:
1301:
1299:
1295:
1289:
1282:Stereoisomers
1279:
1277:
1255:
1242:
1228:
1224:
1214:
1210:
1207:
1203:
1202:
1199:
1197:
1193:
1189:
1179:
1177:
1173:
1169:
1164:
1145:
1137:
1129:
1109:
1098:
1078:
1070:
1062:
1049:
1047:
1038:
1034:
1032:
1028:
1024:
1020:
1016:
1012:
1008:
1004:
995:Cyclopropene
994:
991:
988:
985:
982:
979:
978:
974:
970:
967:
963:
960:
956:
955:
952:
932:
919:
906:
876:
874:
870:
866:
861:
857:
837:
828:
820:
811:
802:
790:
776:
772:
771:methoxyethane
769:
744:
731:
716:
696:
687:
668:
656:
621:
612:
603:
594:
582:
569:
565:
561:
557:
553:
549:
546:(1-propanol,
545:
541:
520:
510:
506:
502:
498:
495:derived from
494:
490:
465:
452:
434:
430:
426:
399:
395:
372:
359:
318:
316:
312:
307:
293:
289:
286:
280:
276:, with roots
274:
269:
264:
260:
256:
253:
249:
243:
218:
216:
215:isotopologues
212:
207:
205:
201:
197:
196:
191:
187:
183:
178:
176:
172:
168:
164:
160:
156:
152:
148:
143:
135:
132:
124:
113:
110:
106:
103:
99:
96:
92:
89:
85:
82: â
81:
77:
76:Find sources:
70:
66:
60:
59:
54:This article
52:
48:
43:
42:
37:
33:
19:
5204:
5198:
5190:
5181:
5173:
5167:
5155:. Retrieved
5130:
5126:
5116:
5108:
5098:
5090:
5081:
5069:. Retrieved
5065:the original
5044:
5039:
5029:
5012:
5008:
5002:
4983:
4976:
4955:
4947:
4904:
4900:
4886:
4874:. Retrieved
4849:
4845:
4835:
4816:
4812:
4754:
4750:
4740:
4725:
4720:
4705:
4699:
4684:
4679:
4664:
4635:
4627:
4606:
4598:
4589:
4568:
4559:
4538:
4530:
4514:
4502:
4487:
4471:
4463:
4458:
4442:
4411:. Retrieved
4392:
4383:
4363:
4356:
4348:
4344:
4312:
4292:
4255:
4247:
4217:Stereocenter
4150:
4145:
3938:
3772:
3760:
3733:
3701:theophylline
3678:
3667:
3648:fumaric acid
3645:
3622:
3606:
3579:
3576:Spin isomers
3461:
3375:
3311:
3098:
3094:
3053:enclosed in
3039:
3009:
3000:atropisomers
2990:/mol). This
2976:
2971:
2963:
2959:
2955:
2951:
2947:
2903:
2899:
2747:
2742:
2572:
2564:
2554:
2550:
2451:
2403:
2353:
2345:
2331:
2327:
2325:
2218:
2214:
2212:
2183:
2179:
2175:
2171:
2167:
2163:
2159:
2059:
2052:
2048:
2045:
2035:
2031:
2027:
2023:
1917:
1910:
1901:-cyclooctene
1898:
1895:
1893:, some not.
1884:
1872:
1864:food science
1860:biochemistry
1849:
1757:
1716:
1652:
1641:
1621:
1612:
1528:
1517:
1422:
1310:
1302:
1298:translations
1291:
1226:
1220:
1195:
1185:
1174:forms of an
1172:zwitterionic
1165:
1050:
1044:
1035:
1030:
1027:cyclopropene
1018:
1011:double bonds
1006:
1000:
992:
986:
980:
902:
869:double bonds
862:
858:
774:
717:
563:
555:
551:
547:
438:
432:
431:2-propanol,
428:
427:1-propanol,
424:
345:
310:
309:
282:= "equal",
254:
219:
208:
203:
193:
179:
174:
150:
144:
142:
127:
118:
108:
101:
94:
87:
75:
63:Please help
58:verification
55:
5157:9 September
5133:(9): 1201.
5105:différentes
3740:enantiomers
3725:amphetamine
3717:Phentermine
3693:vasodilator
3689:theobromine
3652:maleic acid
3610:bond energy
3464:isotopologs
3378:isotopomers
3091:Isotopomers
3035:topoisomers
3006:Topoisomers
2323:complexes.
2199:transplatin
1644:enantiomers
1638:Enantiomers
1628:acetic acid
1608:picoseconds
1425:cyclohexane
1023:triple bond
1005:or allene;
983:Propadiene
905:hydrocarbon
560:propan-2-ol
554:-propanol;
544:propan-1-ol
491:, that is,
5224:Categories
4764:1511.04615
4642:cis, trans
4318:"isomeric"
4276:2001032331
4239:References
3721:non-chiral
3049:, such as
2391:phosphorus
2277:octahedral
2227:, such as
2186:isomers).
1524:vibrations
1176:amino acid
1003:propadiene
288:= "part".
255:isomerisch
190:structural
91:newspapers
5230:Isomerism
4791:2469-9926
4171:Allotropy
4151:In 1848,
4146:isomerism
4121:−
4026:−
3921:−
3876:−
3837:−
3817:fulminate
3777:prepared
3763:cisplatin
3685:xanthines
3274:−
3221:−
3136:deuterium
2996:carboxyls
2916:−
2881:−
2851:−
2821:−
2778:−
2743:staggered
2724:−
2716:−
2686:−
2678:−
2647:−
2603:−
2577:molecule
2557:isomer).
2195:cisplatin
2166:-1,2,3,5-
2140:−
2113:−
2055:isomerism
2005:−
1989:−
1913:Ï orbital
1852:catalysts
1811:−
1787:−
1697:⟶
1691:⟶
1490:−
1482:−
1452:−
1444:−
1294:rotations
1188:resonance
1146:−
1138:−
1117:⇀
1110:−
1099:−
1092:↽
1071:−
1063:−
1046:Tautomers
1041:Tautomers
879:Example:
829:−
821:−
803:−
688:−
669:−
613:−
595:−
521:−
489:propanols
321:Example:
270:ጰÏÏΌΔÏoÏ
263:isomerisk
211:hierarchy
175:Isomerism
155:molecules
147:chemistry
5207:, p. 230
5151:Archived
4939:20443766
4931:23918710
4907:(1998).
4870:Archived
4480:Archived
4435:Archived
4413:21 April
4407:Archived
4321:Archived
4301:Archived
4298:"isomer"
4284:46872308
4227:Tautomer
4164:See also
3697:caffeine
3303:chlorine
3191:) on an
3101:hydrogen
3042:catenane
3031:plasmids
3012:topology
2979:biphenyl
2568:rotamers
2395:halogens
2062:inositol
989:Propyne
860:isomer.
509:hydroxyl
505:hydrogen
501:valences
493:alcohols
273:isĂłmeros
182:chemical
169:of each
80:"Isomer"
18:Isomeric
5135:Bibcode
5071:27 July
5049:Bibcode
4909:Bibcode
4854:Bibcode
4769:Bibcode
4232:Vitamer
3821:cyanate
3769:History
2221:isomers
2038:in the
1868:glucose
1856:enzymes
1666:CHFClBr
1429:Alkanes
1276:benzene
1274:with a
1015:propyne
766:is the
497:propane
259:Swedish
246:) is a
171:element
151:isomers
105:scholar
4937:
4929:
4789:
4732:
4522:
4494:
4449:
4371:
4282:
4274:
4264:
3360:CHDClF
3193:ethane
3078:) and
3051:helium
2983:phenyl
2981:â two
2972:gauche
2968:butane
2964:gauche
2960:gauche
2952:gauche
2904:gauche
2868:, and
2632:methyl
2575:ethane
1648:chiral
1632:dimers
1419:green.
1306:energy
540:oxygen
511:group
252:German
107:
100:
93:
86:
78:
4952:IUPAC
4935:S2CID
4876:1 May
4759:arXiv
4632:IUPAC
4603:IUPAC
4535:IUPAC
3790:AgCNO
3719:is a
3169:, or
3134:) by
3020:cycle
3016:knots
2956:trans
2948:trans
2900:trans
2332:trans
2219:trans
2184:trans
2176:trans
2168:trans
2053:trans
2040:IUPAC
2028:trans
1899:trans
1880:IUPAC
1545:NHFCl
1509:chair
768:ether
285:méros
268:Greek
257:from
195:bonds
167:atoms
112:JSTOR
98:books
5159:2008
5089:".
5073:2012
4927:PMID
4878:2022
4787:ISSN
4730:ISBN
4520:ISBN
4492:ISBN
4447:ISBN
4415:2019
4369:ISBN
4280:OCLC
4272:LCCN
4262:ISBN
4064:and
3941:urea
3891:and
3819:and
3707:and
3514:and
3057:(He@
3026:and
2950:and
2330:and
2217:and
2197:and
2077:CHOH
2034:and
1862:and
1513:boat
1385:and
1296:and
643:and
487:are
279:isos
153:are
84:news
5143:doi
5107:".
5057:doi
5017:doi
4990:doi
4966:doi
4964:".
4917:doi
4905:371
4862:doi
4821:doi
4777:doi
4710:doi
4689:doi
4669:doi
4646:doi
4644:".
4617:doi
4615:".
4549:doi
4547:".
4397:doi
3734:In
3446:ClF
3338:ClF
3279:CDH
3028:RNA
3024:DNA
2958:to
2762:ClH
2703:or
2555:mer
2551:fac
2328:cis
2215:Cis
2180:cis
2172:cis
2164:cis
2160:myo
2049:cis
2024:cis
1742:ClF
1558:or
1427:.
1225:of
1031:III
993:III
871:or
775:III
433:III
184:or
157:or
145:In
67:by
5226::
5149:.
5141:.
5131:85
5129:.
5125:.
5055:.
5045:77
5038:.
5013:48
5011:.
4954:,
4933:.
4925:.
4915:.
4903:.
4899:.
4868:.
4860:.
4850:99
4848:.
4844:.
4817:70
4815:.
4811:.
4799:^
4785:.
4775:.
4767:.
4755:94
4753:.
4749:.
4656:^
4634:,
4605:,
4577:^
4537:,
4423:^
4405:.
4391:.
4332:^
4278:.
4270:.
4078:NH
3953:CH
3687:,
3654::
3631:.
3620:.
3459:.
3434:CH
3326:CH
3309:.
3258:DH
3226:CH
3205:HD
3073:20
3064:20
3037:.
3002:.
2988:kJ
2933:Cl
2921:CH
2885:Cl
2855:Cl
2847:Cl
2838:,
2795:Cl
2783:CH
2608:CH
2570:.
2462:MX
2427:Cl
2414:PF
2376:Cl
2364:PF
2288:MX
2240:MX
2117:OH
2009:Cl
2001:CH
1993:HC
1985:Cl
1954:Cl
1882:.
1847:.
1816:CH
1807:CH
1791:CH
1730:CH
1700:Br
1694:Cl
1650:.
1311:A
1300:.
1256:10
1178:.
1163:.
1029:;
1019:II
987:II
951::
856:.
834:CH
808:CH
715:.
693:CH
680:OH
673:CH
630:OH
618:CH
600:CH
564:II
525:OH
429:II
423::
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