1103:
1096:
1089:
983:
976:
990:
383:
390:
376:
1342:
1168:
1148:
1309:
1413:
1182:
1175:
1141:
1134:
496:
489:
482:
1288:
1387:
770:) are structurally equivalent to each other, as are the two carbons; because any hydrogen can be switched with any other, either by a permutation that swaps just those two atoms, or by a permutation that swaps the two carbons and each hydrogen in one methyl group with a different hydrogen on the other methyl. Either operation preserves the structure of the molecule. That is the case also for the hydrogen atoms
1266:
36:
1365:
932:. However, with that replacement, the atom permutations that moved that hydrogen are no longer valid. Only one permutation remains, that corresponds to flipping the molecule over while keeping the chlorine fixed. The five remaining hydrogens then fall into three different equivalence classes: the one opposite to the chlorine is a class by itself (called the
637:. The infrared spectrum is largely determined by the vibration modes of the molecule, and functional groups like hydroxyl and esters have very different vibration modes. Thus 1-propanol and 2-propanol have relatively similar infrared spectra because of the hydroxyl group, which are fairly different from that of methyl ethyl ether.
928:. Its six hydrogens are all structurally equivalent, and so are the six carbons; because the structure is not changed if the atoms are permuted in ways that correspond to flipping the molecule over or rotating it by multiples of 60 degrees. Therefore, replacing any hydrogen by chlorine yields only one
682:
atoms (H) may yield any of two structural isotopomers (1,1-dideuteroethene and 1,2-dideuteroethene), if both carbon atoms are the same isotope. If, in addition, the two carbons are different isotopes (say, C and C), there would be three distinct structural isotopomers, since 1-C-1,1-dideuteroethene
1206:
Enumerating or counting structural isomers in general is a difficult problem, since one must take into account several bond types (including delocalized ones), cyclic structures, and structures that cannot possibly be realized due to valence or geometric constraints, and non-separable tautomers.
708:
if each atom of A can be paired with an atom of B of the same element, in a one-to-one way, so that for every bond in A there is a bond in B, of the same type, between corresponding atoms; and vice versa. This requirement applies also to complex bonds that involve three or more atoms, such as the
920:
Once a substitution is made on a parent molecule, its structural symmetry is usually reduced, meaning that atoms that were formerly equivalent may no longer be so. Thus substitution of two or more equivalent atoms by the same element may generate more than one positional isomer.
1052:
On the other hand, the second replacement (by the same substituent) may preserve or even increase the symmetry of the molecule, and thus may preserve or reduce the number of equivalence classes for the next replacement. Thus, the four remaining hydrogens in
818:
Structural equivalences between atoms of a parent molecule reduce the number of positional isomers that can be obtained by replacing those atoms for a different element or group. Thus, for example, the structural equivalence between the six hydrogens of
805:
are not all structurally equivalent. The six hydrogens attached to the first and third carbons are equivalent, as in ethane, and the two attached to the middle carbon are equivalent to each other; but there is no equivalence between these two
667:) one may treat different isotopes of the same element as different elements. In the second case, two molecules with the same number of atoms of each isotope but distinct bonding schemes are said to be
892:
are partitioned into two structural equivalence classes (the six on the methyl groups, and the two on the central carbon); therefore there are only two positional isomers of propanol (
719:
Two molecules then can be said to be structural isomers (or, if isotopes matter, structural isotopomers) if they have the same molecular formula but do not have the same structure.
1065:- are all equivalent again. Still, some of these 3 + 2 + 1 = 6 substitutions end up yielding the same structure, so there are only three structurally distinct
281:, in which the atoms and bonding scheme are the same, but only the relative spatial arrangement of the atoms is different. Examples of the latter are the
338:
of a compound is a structural isomer that differs from it in the atoms and bonds that are considered to comprise the "skeleton" of the molecule. For
683:
would be different from 1-C-2,2-dideuteroethene. And, in both cases, the 1,2-dideutero structural isotopomer would occur as two stereoisotopomers,
731:
of the atoms that exchanges at least two atoms but does not change the molecule's structure. Two atoms then can be said to be structurally
436:
716:
Depending on the context, one may require that each atom be paired with an atom of the same isotope, not just of the same element.
660:
1222:
having different bond connectivities. Seven of them are air-stable at room temperature, and these are given in the table below.
1751:
1608:
17:
1560:
1740:
1720:
1700:
1680:
1632:
1570:
1545:
1522:
678:
would have no structural isomers under the first interpretation; but replacing two of the hydrogen atoms (H) by
626:
are structural isomers, but not functional isomers, since they have the same significant functional group (the
101:
is another compound whose molecule has the same number of atoms of each element, but with logically distinct
742:
are structurally equivalent, because any permutation of them will preserve all the bonds of the molecule.
1460:
1126:, which is benzene with one hydroxyl substituent and two methyl substituents, has a total of 6 isomers:
190:
The concept applies also to polyatomic ions with the same total charge. A classical example is the
1321:
1582:
1450:
1445:
1122:
If the substituents at each step are different, there will usually be more structural isomers.
1078:
1074:
1070:
783:
664:
233:
634:
530:
46:
732:
53:
944:). Thus a second substitution of hydrogen by chlorine can yield three positional isomers:
8:
1233:
961:
953:
945:
599:
464:
132:
1599:
Poppe, Laszlo; Nagy, Jozsef; Hornyanszky, Gabor; Boros, Zoltan; Mihaly, Nogradi (2016).
526:
522:
1769:
1406:
656:
1513:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell (2009):
1736:
1716:
1696:
1676:
1628:
1604:
1566:
1541:
1518:
1228:
807:
173:
98:
533:, each of which has three double bonds, but on different positions along the chain.
1649:
1487:
1066:
710:
545:
453:
452:) are structural isomers that can be viewed as differing only on the position of a
339:
252:
207:
633:
Besides the different chemistry, functional isomers typically have very different
1671:
1436:
of the carbonyl isomers (propionaldehyde and acetone), but these are not stable.
1380:
1302:
420:
61:
1479:
603:
57:
1763:
1281:
1259:
1246:
1238:
989:
982:
975:
929:
795:
154:
102:
27:
Chemical compounds with the same atoms but arranged and connected differently
1654:
1492:
300:
Among the structural isomers, one can distinguish several classes including
1455:
771:
278:
1102:
1095:
1088:
1034:
728:
548:, resulting in significantly different chemical and physical properties.
513:
508:
503:
457:
389:
382:
1399:
897:
893:
646:
623:
619:
411:
406:
362:
358:
282:
1341:
1210:
For example, there are nine structural isomers with molecular formula
375:
1167:
1147:
727:
Structural symmetry of a molecule can be defined mathematically as a
679:
199:
82:
1308:
437:
Arene substitution pattern § Ortho, meta, and para substitution
1538:
Useful
Principles in Chemistry for Agriculture and Nursing Students
1433:
1412:
905:
787:
779:
627:
576:
552:
318:
294:
655:
of the same element. However, in some situations (for instance in
495:
488:
481:
474:
parent molecule can give any of three different position isomers:
346:, that usually means the carbon atoms and the bonds between them.
1386:
1358:
1335:
1123:
1038:
925:
909:
901:
869:
844:
802:
739:
652:
587:
564:
468:
401:
350:
343:
191:
113:
1287:
1265:
206:. It is also extended to ionic compounds, so that (for example)
1057:-dichlorobenzene still fall into three classes, while those of
1046:
1042:
1030:
936:
position), the two closest to the chlorine form another class (
820:
791:
775:
746:
735:
if there is a structural symmetry that takes one to the other.
675:
580:
274:
1601:
1181:
1174:
1140:
1133:
575:: the first has a –C(=O)H functional group, which makes it an
1211:
615:
94:
579:, whereas the second has a C–C(=O)–C group, that makes it a
463:
For example, replacing one of the 12 hydrogen atoms –H by a
1430:
722:
285:, whose molecules are mirror images of each other, and the
218:
1364:
1598:
460:, or some other feature on the same "parent" structure.
651:
In chemistry, one usually ignores distinctions between
1559:
William F. Bynum, E. Janet Browne, Roy Porter (2014):
713:
in the benzene molecule and other aromatic compounds.
694:
430:
915:
900:). Likewise there are only two positional isomers of
813:
1201:
843:means that there is just one structural isomer of
704:Two molecules (including polyatomic ions) A and B
423:, as in the above example, one may use the term
349:For example, there are three skeletal isomers of
273:Structural isomerism is the most radical type of
1761:
1713:A Textbook of Science for the Health Professions
1603:. Weinheim, Germany: Wiley-VCH. pp. 26–27.
1320:Tautomeric with prop-1-en-1-ol, which has both
940:), and the remaining two are the third class (
738:Thus, for example, all four hydrogen atoms of
232:are considered structural isomers, and so are
924:The classical example is the derivatives of
544:are structural isomers which have different
1555:
1553:
187:but are three distinct structural isomers.
1693:General, Organic, and Biological Chemistry
1532:
1530:
357:-pentane (often called simply "pentane"),
1731:Jean-Loup Faulon, Andreas Bender (2010):
1672:Contemporary Theory of Chemical Isomerism
1653:
1491:
801:On the other hand, the hydrogen atoms of
699:
640:
1725:
1705:
1685:
1646:IUPAC Compendium of Chemical Terminology
1637:
1592:
1575:
1550:
1515:Introduction to Organic and Biochemistry
1472:
723:Structural symmetry and equivalent atoms
109:was formerly used for the same concept.
1733:Handbook of Chemoinformatics Algorithms
1663:
1617:
1527:
1507:
1029:For the same reason, there is only one
536:
14:
1762:
1752:CRC Handbook of Chemistry and Physics
1623:D. Brynn Hibbert, A.M. James (1987):
329:
1562:Dictionary of the History of Science
521:Another example of regioisomers are
29:
695:Structural equivalence and symmetry
431:Position isomerism (regioisomerism)
24:
916:Symmetry breaking by substitutions
25:
1781:
1625:Macmillan Dictionary of Chemistry
814:Symmetry and positional isomerism
1411:
1385:
1363:
1340:
1307:
1286:
1264:
1180:
1173:
1166:
1146:
1139:
1132:
1101:
1094:
1087:
988:
981:
974:
868:, not 6. The eight hydrogens of
494:
487:
480:
388:
381:
374:
34:
1745:
1429:Two structural isomers are the
1202:Isomer enumeration and counting
1128:
1083:
970:
745:Likewise, all six hydrogens of
476:
367:
1061:- fall into two, and those of
13:
1:
1466:
60:in tone and meet Knowledge's
1353:Tautomeric with propen-2-ol
1033:(hydroxybenzene), but three
630:–OH) and are both alcohols.
586:Another example is the pair
369:Skeletal isomers of pentane
7:
1695:, 7th edition. 1232 pages.
1461:Metamerism (disambiguation)
1439:
1041:(methylbenzene), but three
10:
1786:
1691:H. Stephen Stoker (2015):
1540:, 2nd Edition. 281 pages.
1480:"Constitutional isomerism"
1423:
1420:
1417:
1410:
1405:
1397:
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1384:
1379:
1375:
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1357:
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1339:
1334:
1319:
1316:
1313:
1306:
1301:
1297:
1294:
1292:
1285:
1280:
1276:
1273:
1270:
1263:
1258:
644:
434:
1711:Barry G. Hinwood (1997):
1669:Zdenek Slanina (1986):
1660:online ver. 3.0.1 2019.
1655:10.1351/goldbook.I03352
1536:Peter P. Mumba (2018):
1493:10.1351/goldbook.C01285
1116:1,3,5-Trichlorobenzene
1113:1,2,4-Trichlorobenzene
1110:1,2,3-Trichlorobenzene
706:have the same structure
551:An example is the pair
105:between them. The term
1648:(3rd ed.). 2006.
1583:"Structural isomerism"
1451:Descriptor (chemistry)
1446:Coordination isomerism
784:hexamethylenetetramine
700:Structural equivalence
669:structural isotopomers
665:microwave spectroscopy
641:Structural isotopomers
531:octadecatrienoic acids
324:structural isotopomers
234:methylammonium formate
361:(2-methylbutane) and
91:constitutional isomer
18:Constitutional isomer
1329:stereoisomeric forms
1023:1,4-Dichlorobenzene
1020:1,3-Dichlorobenzene
1017:1,2-Dichlorobenzene
537:Functional isomerism
277:. It is opposed to
54:improve this article
1234:Molecular structure
808:equivalence classes
711:delocalized bonding
674:Thus, for example,
419:If the skeleton is
370:
365:(dimethylpropane).
306:positional isomers
133:methyl propyl ether
97:nomenclature) of a
1581:Jim Clark (2000).
1407:Methyl vinyl ether
1400:enantiomeric forms
542:Functional isomers
446:positional isomers
368:
330:Skeletal isomerism
314:functional isomers
1610:978-3-527-33901-3
1427:
1426:
1229:Chemical compound
1199:
1198:
1120:
1119:
1067:trichlorobenzenes
1027:
1026:
1012:-Dichlorobenzene
1006:-Dichlorobenzene
1000:-Dichlorobenzene
546:functional groups
527:γ-linolenic acids
519:
518:
467:group –OH on the
417:
416:
340:organic compounds
174:molecular formula
87:structural isomer
79:
78:
62:quality standards
16:(Redirected from
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1723:
1709:
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1689:
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1136:
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1098:
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992:
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978:
971:
966:-dichlorobenzene
891:
890:
889:
881:
880:
867:
865:
864:
856:
855:
842:
841:
840:
832:
831:
769:
768:
767:
759:
758:
635:infrared spectra
618:). In contrast,
498:
491:
484:
477:
454:functional group
442:Position isomers
392:
385:
378:
371:
302:skeletal isomers
269:
253:ammonium acetate
250:
231:
216:
208:ammonium cyanate
205:
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1498:
1496:
1486:. IUPAC. 2014.
1484:IUPAC Gold Book
1478:
1477:
1473:
1469:
1442:
1381:Propylene oxide
1303:Propionaldehyde
1248:
1240:
1219:
1215:
1204:
918:
904:, and three of
888:
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439:
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425:chain isomerism
336:skeletal isomer
332:
279:stereoisomerism
267:
263:
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15:
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5:
1783:
1773:
1772:
1757:
1756:
1744:
1724:
1704:
1684:
1662:
1644:"Isotopomer".
1636:
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1609:
1591:
1574:
1549:
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1383:
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1351:
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1345:
1338:
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1331:
1318:
1315:
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1305:
1299:
1298:
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1291:
1284:
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1256:
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1236:
1231:
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1213:
1203:
1200:
1197:
1196:
1193:
1190:
1186:
1185:
1178:
1171:
1163:
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1159:
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1151:
1144:
1137:
1118:
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1114:
1111:
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1106:
1099:
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1025:
1024:
1021:
1018:
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1013:
1007:
1001:
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993:
986:
979:
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914:
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877:
861:
852:
837:
828:
815:
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764:
755:
724:
721:
701:
698:
696:
693:
645:Main article:
642:
639:
611:
607:
604:dimethyl ether
595:
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538:
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516:
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379:
331:
328:
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172:have the same
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42:
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33:
26:
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1782:
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1765:
1753:
1748:
1742:
1741:9781420082999
1738:
1735:. 454 pages.
1734:
1728:
1722:
1721:9780748733774
1718:
1715:. 489 pages.
1714:
1708:
1702:
1701:9781305686182
1698:
1694:
1688:
1682:
1681:9789027717078
1678:
1675:. 254 pages.
1674:
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1640:
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1633:9781349188178
1630:
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1572:
1571:9781400853410
1568:
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1546:9781618965288
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1523:9780495391166
1520:
1517:. 752 pages.
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1304:
1300:
1289:
1283:
1282:Cyclopropanol
1279:
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1260:Allyl alcohol
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930:chlorobenzene
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903:
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846:
822:
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796:dodecahedrane
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563:–C(=O)-H and
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155:diethyl ether
134:
115:
112:For example,
110:
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84:
73:
63:
59:
55:
49:
48:
45:reads like a
43:This article
41:
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1627:. page 263.
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1586:
1577:
1565:. page 218.
1561:
1537:
1514:
1509:
1497:. Retrieved
1483:
1474:
1456:Stereoisomer
1428:
1326:
1322:
1209:
1205:
1195:3,5-Xylenol
1192:3,4-Xylenol
1189:2,6-Xylenol
1161:2,5-Xylenol
1158:2,4-Xylenol
1155:2,3-Xylenol
1121:
1062:
1058:
1054:
1051:
1045:, and three
1035:benzenediols
1028:
1009:
1003:
997:
963:
955:
947:
941:
937:
933:
923:
919:
817:
800:
772:cyclopentane
744:
737:
726:
718:
715:
705:
703:
688:
684:
673:
668:
650:
632:
585:
550:
541:
540:
520:
469:
462:
450:regioisomers
449:
445:
441:
440:
424:
418:
397:
354:
348:
335:
333:
323:
317:
313:
310:regioisomers
309:
305:
301:
299:
293:versions of
290:
286:
272:
215:][O=C=N]
189:
111:
106:
90:
86:
80:
67:
44:
729:permutation
523:α-linolenic
514:Pentan-3-ol
509:Pentan-2-ol
504:Pentan-1-ol
458:substituent
283:enantiomers
70:August 2020
56:to make it
1467:References
1037:; and one
898:2-propanol
894:1-propanol
733:equivalent
647:Isotopomer
624:2-propanol
620:1-propanol
571:C–C(=O)–CH
435:See also:
412:Neopentane
407:Isopentane
363:neopentane
359:isopentane
342:, such as
1770:Isomerism
1587:Chemguide
1434:tautomers
680:deuterium
319:tautomers
275:isomerism
245:][HCO
200:fulminate
83:chemistry
1764:Category
1754:65th ed.
1440:See also
1398:Has two
1295:101–102
1254:Comment
962:1,4- or
954:1,3- or
946:1,2- or
906:pentanol
788:prismane
780:2-butyne
653:isotopes
628:hydroxyl
598:–OH (an
577:aldehyde
553:propanal
472:-pentane
465:hydroxyl
295:2-butene
198:and the
99:compound
47:textbook
1499:19 July
1359:Oxetane
1336:Acetone
1247:Boiling
1239:Melting
1124:Xylenol
1047:xylenes
1043:toluols
1039:toluene
926:benzene
910:hexanol
902:butanol
870:propane
845:ethanol
803:propane
798:, etc.
740:methane
600:alcohol
588:ethanol
565:acetone
529:, both
421:acyclic
402:Pentane
351:pentane
344:alkanes
260:][H
256:[NH
211:[NH
192:cyanate
114:butanol
107:metamer
93:in the
58:neutral
52:Please
1739:
1719:
1699:
1679:
1631:
1607:
1589:, n.l.
1569:
1544:
1521:
1350:56.53
1347:–94.9
1079:1,3,5-
1077:, and
1075:1,2,4-
1071:1,2,3-
1031:phenol
960:, and
821:ethane
792:cubane
776:allene
747:ethane
676:ethene
614:H (an
610:C–O–CH
602:) and
581:ketone
444:(also
322:, and
237:[H
153:, and
1418:–122
1392:–112
1327:trans
1271:–129
1249:point
1241:point
1059:ortho
998:ortho
948:ortho
938:ortho
689:trans
663:, or
657:Raman
616:ether
291:trans
204:C≡N−O
196:O=C=N
148:−O−CH
140:C−(CH
121:C−(CH
103:bonds
95:IUPAC
1737:ISBN
1717:ISBN
1697:ISBN
1677:ISBN
1629:ISBN
1605:ISBN
1567:ISBN
1542:ISBN
1519:ISBN
1501:2018
1431:enol
1370:–97
1325:and
1314:–81
1251:(°C)
1243:(°C)
1063:para
1055:meta
1010:para
1004:meta
964:para
956:meta
942:meta
934:para
896:and
687:and
622:and
594:C–CH
559:C–CH
525:and
308:(or
289:and
264:C−CO
251:and
241:C−NH
219:urea
217:and
202:ion
194:ion
89:(or
85:, a
1650:doi
1585:in
1488:doi
1395:34
1373:48
1323:cis
1317:48
1274:97
908:or
685:cis
661:NMR
448:or
312:),
287:cis
230:C=O
226:N−)
162:CCH
129:−OH
81:In
1766::
1552:^
1529:^
1482:.
1421:6
1081:.
1073:,
1069::
1049:.
968:.
952:,
912:.
866:OH
810:.
794:,
790:,
786:,
782:,
778:,
774:,
691:.
671:.
659:,
583:.
456:,
427:.
353::
334:A
326:.
316:,
304:,
297:.
270:.
222:(H
183:10
166:−)
158:(H
131:,
1658:.
1652::
1613:.
1503:.
1490::
1220:O
1218:6
1216:H
1214:3
1212:C
958:-
950:-
887:8
882:H
878:3
873:C
862:5
857:H
853:2
848:C
838:6
833:H
829:2
824:C
765:6
760:H
756:2
751:C
749:(
612:2
608:3
606:H
596:2
592:3
590:H
573:3
569:3
567:H
561:2
557:3
555:H
470:n
400:-
398:n
355:n
268:]
266:2
262:3
258:4
249:]
247:2
243:3
239:3
228:2
224:2
213:4
185:O
181:H
179:4
177:C
170:O
168:2
164:2
160:3
150:3
146:2
144:)
142:2
138:3
136:H
127:3
125:)
123:2
119:3
117:H
72:)
68:(
64:.
50:.
20:)
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