662:
346:
316:
331:
628:
920:
839:
645:
825:
811:
894:
75:
724:
906:
752:
738:
192:
Although the specifics vary depending on the compound, in simple disubstituted arenes, the three isomers tend to have rather similar boiling points. However, the
1035:
1006:
1543:
220:
directors, separation of these isomers is a common problem in synthetic chemistry. Several methods exist in order to separate these isomers:
1078:"On distingue facilement ces trois séries, dans lesquelles les dérivés bihydroxyliques ont leurs terms correspondants, par les préfixes
96:, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and
17:
1503:
1219:
1562:
1092:(One easily distinguishes these three series â in which the dihydroxy derivatives have their corresponding terms â by the prefixes
40:
367:
83:
1418:
196:
isomer usually has the highest melting point, and the lowest solubility in a given solvent, of the three isomers.
514:
1626:
1585:
1212:
242:
1151:
1523:
1621:
509:
description was historically used to designate the original compound, and an isomer was often called the
1399:
1130:
577:- to denote specific relative locations of the substituents on a disubstituted aromatic ring (namely
661:
345:
330:
315:
280:. These isomers can often be separated by distillation. These separated isomers can be converted to
1602:
1205:
1065:
765:
1268:
838:
522:
1494:
1259:
1118:
938:
824:
517:
and trimetaphosphoric acid have nothing to do with aromatics at all. Likewise, the description
919:
1441:
1381:
224:
627:
366:
describes two substituents sharing the same ring position in an intermediate compound in an
1445:
948:
644:
232:
52:
8:
810:
1356:
124:, the substituents occupy the opposite ends (positions 1 and 4, corresponding to R and
1070:
Bulletins de l'Académie royale des sciences, des lettres et des beaux-arts de
Belgique
868:
844:
801:
37:
31:
1045:
1016:
550:
505:, respectively. The relationship to the current meaning is perhaps not obvious. The
1049:
1040:
1020:
1011:
905:
830:
793:
751:
678:
590:
893:
1248:
1228:
1066:"Faits pour servir à la détermination du lieu chimique dans la série aromatique"
723:
1464:
371:
281:
265:
169:
737:
1615:
1044:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1015:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
816:
785:
530:
452:
277:
1068:(Facts to be used in determining chemical location in the aromatic series),
1053:
1024:
562:
1294:
911:
864:
757:
714:
582:
534:
157:
451:, the entering group takes up a position adjacent to that occupied by the
1152:"Untersuchungen ĂŒber die Constitution der zweifach-substituirten Benzole"
925:
880:
852:
578:
424:
386:
153:
44:
743:
706:
407:
375:
1243:
382:
254:
133:
472:
occurs when the new position is more than one atom away on the ring.
1476:
1117:(Braunschweig, Germany: Friedrich Vieweg und Sohn, 1874), vol. 1,
860:
856:
729:
698:
667:
650:
633:
549:
to distinguish isomers of disubstituted aromatic rings starts with
411:
249:
product, relying on the principle that it is less soluble than the
149:
48:
1197:
110:
the substituents occupy positions 1 and 3 (corresponding to R and
74:
586:
526:
173:
1154:(Investigations into the structure of di-substituted benzenes),
943:
876:
606:
602:
403:
177:
460:
253:
and thus will crystallise first. Care must be taken to avoid
145:
136:
serve as an example for these three types of substitution.
997:, Allyn and Bacon Inc, Boston, 1959. Ch. 21, pp. 573-574.
863:
atom is considered one of the substituents. For example,
1076: : 166-185; see especially p. 169. From p. 169:
601:
Examples of the use of this nomenclature are given for
521:
was reserved for just closely related compounds. Thus
199:
58:
984:, Allyn and Bacon Inc, Boston, 1959. Ch. 10, p. 290.
296:
168:-directors, and electron withdrawing groups such as
1171:William B. Jensen (March 2006) "The origins of the
561:prefix to a 1,2-isomer. It was the German chemist
971:, Allyn and Bacon Inc, Boston, 1959. Ch.9, p. 250.
589:. The current nomenclature was introduced by the
1613:
406:position. It is observed in compounds such as
27:Position of molecules attached to benzene rings
764:There are three arene substitution isomers of
677:There are three arene substitution isomers of
1213:
1162: : 265-301; see especially pp. 299-300.
851:These terms can also be used in six-membered
431:
875:substitutions on a pyridine ring, while the
533:"paratartaric acid" (another obsolete term:
513:compound. For instance, the trivial names
1220:
1206:
427:for substituents at the 1 and 8 positions.
227:will often separate these isomers, as the
212:Because electron donating groups are both
1131:"Ueber die Constitution des Naphthalins"
73:
1524:Pseudoasymmetric (pseudochiral) centers
1504:CIP (CahnâIngoldâPrelog) priority rules
402:refers to the substituents occupying a
14:
1614:
1183:- prefixes in chemical nomenclature,"
585:first applied GrÀbe's nomenclature to
565:who, in 1869, first used the prefixes
144:Electron donating groups, for example
1201:
1141: : 20-28; see especially p. 26.
493:are all derived from Greek, meaning
1227:
1133:(On the structure of naphthalene),
537:) in 1830. The use of the prefixes
368:electrophilic aromatic substitution
84:Electrophilic aromatic substitution
24:
1041:Compendium of Chemical Terminology
1012:Compendium of Chemical Terminology
25:
1638:
553:in 1867, although he applied the
1156:Annalen der Chemie und Pharmacie
1135:Annalen der Chemie und Pharmacie
918:
904:
892:
837:
823:
809:
750:
736:
722:
660:
643:
626:
581:). In 1870, the German chemist
344:
329:
314:
78:Main arene substitution patterns
51:in relation to each other on an
1165:
1115:Neues Handwörterbuch der Chemie
557:prefix to a 1,4-isomer and the
284:and used to prepare other pure
1144:
1123:
1107:
1058:
1029:
1000:
987:
974:
961:
13:
1:
1185:Journal of Chemical Education
954:
459:-substitution is observed in
276:isomers have quite different
187:
43:and pinpoint the position of
139:
7:
932:
596:
245:can be used to obtain pure
10:
1643:
1586:Octahedral propeller twist
1322:Arene substitution pattern
1113:Hermann von Fehling, ed.,
476:
243:Fractional crystallisation
81:
18:Aromatic ortho substituent
1600:
1584:
1561:
1542:
1522:
1502:
1493:
1475:
1463:
1440:
1417:
1398:
1380:
1355:
1320:
1293:
1267:
1260:Configuration descriptors
1258:
1235:
855:aromatic systems such as
1603:Category:Stereochemistry
766:benzenedicarboxylic acid
1495:Absolute configurations
1400:Three identical ligands
1064:Wilhelm Körner (1867)
1054:10.1351/goldbook.T06256
1025:10.1351/goldbook.C01081
385:groups can form stable
1563:Relative configuration
939:Descriptor (chemistry)
525:originally called the
79:
1627:Chemical nomenclature
1382:Syn and anti addition
225:Column chromatography
77:
34:substitution patterns
1412:(facies, meridonal)
1150:Victor Meyer (1870)
949:Structural isomerism
523:Jöns Jakob Berzelius
515:orthophosphoric acid
53:aromatic hydrocarbon
1419:In carbon skeletons
993:Morrison and Boyd,
980:Morrison and Boyd,
967:Morrison and Boyd,
180:groups, tend to be
1622:Aromatic compounds
160:groups tend to be
80:
41:IUPAC nomenclature
1609:
1608:
1596:
1595:
1489:
1488:
1046:tele-substitution
1017:cine-substitution
995:Organic Chemistry
982:Organic Chemistry
969:Organic Chemistry
845:terephthalic acid
802:terephthalic acid
393:directing groups.
255:cocrystallisation
38:organic chemistry
16:(Redirected from
1634:
1578:
1577:
1572:
1571:
1544:Optical rotation
1500:
1499:
1265:
1264:
1222:
1215:
1208:
1199:
1198:
1192:
1169:
1163:
1148:
1142:
1127:
1121:
1111:
1105:
1062:
1056:
1033:
1027:
1004:
998:
991:
985:
978:
972:
965:
922:
908:
896:
841:
831:isophthalic acid
827:
813:
794:isophthalic acid
754:
740:
726:
679:dihydroxybenzene
664:
647:
630:
591:Chemical Society
455:. For example,
348:
333:
318:
128:in the diagram).
114:in the diagram).
21:
1642:
1641:
1637:
1636:
1635:
1633:
1632:
1631:
1612:
1611:
1610:
1605:
1592:
1580:
1575:
1574:
1569:
1568:
1557:
1538:
1518:
1485:
1471:
1459:
1436:
1413:
1394:
1376:
1351:
1316:
1289:
1254:
1253:
1249:Racemic mixture
1231:
1229:Stereochemistry
1226:
1196:
1195:
1191:(3) : 356.
1170:
1166:
1149:
1145:
1128:
1124:
1112:
1108:
1063:
1059:
1034:
1030:
1005:
1001:
992:
988:
979:
975:
966:
962:
957:
935:
928:
923:
914:
909:
900:
897:
847:
842:
833:
828:
819:
814:
779:
775:
771:
760:
755:
746:
741:
732:
727:
692:
688:
684:
673:
665:
656:
648:
639:
631:
620:
616:
612:
599:
479:
441:
355:
354:- substitution.
349:
340:
339:- substitution.
334:
325:
324:- substitution.
319:
310:
282:diazonium salts
266:nitro compounds
210:
190:
142:
86:
72:
28:
23:
22:
15:
12:
11:
5:
1640:
1630:
1629:
1624:
1607:
1606:
1601:
1598:
1597:
1594:
1593:
1590:
1588:
1582:
1581:
1567:
1565:
1559:
1558:
1549:(+)-, (â)- or
1548:
1546:
1540:
1539:
1528:
1526:
1520:
1519:
1508:
1506:
1497:
1491:
1490:
1487:
1486:
1481:
1479:
1473:
1472:
1469:
1467:
1465:Spiro compound
1461:
1460:
1450:
1448:
1438:
1437:
1423:
1421:
1415:
1414:
1404:
1402:
1396:
1395:
1386:
1384:
1378:
1377:
1368:
1366:
1353:
1352:
1326:
1324:
1318:
1317:
1306:
1304:
1291:
1290:
1280:
1278:
1262:
1256:
1255:
1252:
1251:
1246:
1240:
1239:
1237:
1233:
1232:
1225:
1224:
1217:
1210:
1202:
1194:
1193:
1164:
1143:
1129:Graebe (1869)
1122:
1106:
1072:, 2nd series,
1057:
1028:
999:
986:
973:
959:
958:
956:
953:
952:
951:
946:
941:
934:
931:
930:
929:
924:
917:
915:
910:
903:
901:
898:
891:
849:
848:
843:
836:
834:
829:
822:
820:
815:
808:
780:) – the
777:
773:
769:
762:
761:
756:
749:
747:
742:
735:
733:
728:
721:
693:) – the
690:
686:
682:
675:
674:
666:
659:
657:
649:
642:
640:
632:
625:
618:
614:
610:
598:
595:
551:Wilhelm Körner
478:
475:
474:
473:
464:
440:
430:
429:
428:
415:
394:
372:Trimethylsilyl
357:
356:
350:
343:
341:
335:
328:
326:
320:
313:
309:
295:
294:
293:
278:boiling points
262:
240:
209:
200:Separation of
198:
189:
186:
141:
138:
130:
129:
115:
101:
71:
57:
26:
9:
6:
4:
3:
2:
1639:
1628:
1625:
1623:
1620:
1619:
1617:
1604:
1599:
1589:
1587:
1583:
1566:
1564:
1560:
1556:
1552:
1547:
1545:
1541:
1536:
1532:
1527:
1525:
1521:
1516:
1512:
1507:
1505:
1501:
1498:
1496:
1492:
1484:
1480:
1478:
1474:
1468:
1466:
1462:
1457:
1453:
1449:
1447:
1443:
1439:
1434:
1430:
1426:
1422:
1420:
1416:
1411:
1407:
1403:
1401:
1397:
1393:
1389:
1385:
1383:
1379:
1375:
1371:
1367:
1365:
1363:
1359:
1354:
1349:
1345:
1341:
1337:
1333:
1329:
1325:
1323:
1319:
1314:
1310:
1305:
1303:
1301:
1297:
1292:
1287:
1283:
1279:
1277:
1275:
1271:
1266:
1263:
1261:
1257:
1250:
1247:
1245:
1242:
1241:
1238:
1234:
1230:
1223:
1218:
1216:
1211:
1209:
1204:
1203:
1200:
1190:
1186:
1182:
1178:
1174:
1168:
1161:
1157:
1153:
1147:
1140:
1136:
1132:
1126:
1120:
1116:
1110:
1103:
1099:
1095:
1091:
1087:
1083:
1079:
1075:
1071:
1067:
1061:
1055:
1051:
1047:
1043:
1042:
1037:
1032:
1026:
1022:
1018:
1014:
1013:
1008:
1003:
996:
990:
983:
977:
970:
964:
960:
950:
947:
945:
942:
940:
937:
936:
927:
921:
916:
913:
907:
902:
895:
890:
889:
888:
886:
882:
878:
874:
870:
866:
862:
858:
854:
846:
840:
835:
832:
826:
821:
818:
817:phthalic acid
812:
807:
806:
805:
803:
799:
795:
791:
787:
786:phthalic acid
783:
767:
759:
753:
748:
745:
739:
734:
731:
725:
720:
719:
718:
716:
712:
708:
704:
700:
696:
680:
672:
670:
663:
658:
655:
653:
646:
641:
638:
636:
629:
624:
623:
622:
608:
604:
594:
592:
588:
584:
580:
576:
572:
568:
564:
560:
556:
552:
548:
544:
540:
536:
532:
531:tartaric acid
528:
524:
520:
516:
512:
508:
504:
500:
496:
492:
488:
484:
481:The prefixes
471:
470:-substitution
469:
465:
462:
458:
454:
453:leaving group
450:
449:-substitution
448:
443:
442:
438:
434:
426:
422:
421:-substitution
420:
416:
413:
409:
405:
401:
400:-substitution
399:
395:
392:
388:
384:
380:
378:
373:
369:
365:
364:-substitution
363:
359:
358:
353:
347:
342:
338:
332:
327:
323:
317:
312:
311:
307:
303:
299:
291:
287:
283:
279:
275:
271:
267:
263:
260:
256:
252:
248:
244:
241:
238:
234:
230:
226:
223:
222:
221:
219:
215:
207:
203:
197:
195:
185:
183:
179:
175:
171:
167:
163:
159:
155:
151:
147:
137:
135:
127:
123:
122:-substitution
121:
116:
113:
109:
108:-substitution
107:
102:
99:
95:
94:-substitution
93:
88:
87:
85:
76:
69:
65:
61:
56:
54:
50:
46:
42:
39:
35:
33:
19:
1554:
1550:
1534:
1530:
1514:
1510:
1482:
1455:
1451:
1432:
1428:
1424:
1409:
1405:
1391:
1387:
1373:
1369:
1361:
1357:
1347:
1343:
1339:
1335:
1331:
1327:
1321:
1312:
1308:
1299:
1295:
1285:
1281:
1273:
1269:
1188:
1184:
1180:
1176:
1172:
1167:
1159:
1155:
1146:
1138:
1134:
1125:
1114:
1109:
1101:
1097:
1093:
1089:
1085:
1081:
1077:
1073:
1069:
1060:
1039:
1031:
1010:
1002:
994:
989:
981:
976:
968:
963:
912:nicotinamide
884:
872:
865:nicotinamide
859:, where the
853:heterocyclic
850:
797:
789:
781:
763:
758:hydroquinone
715:hydroquinone
710:
702:
694:
676:
668:
651:
634:
600:
583:Viktor Meyer
574:
570:
566:
558:
554:
546:
542:
538:
535:racemic acid
518:
510:
506:
502:
498:
494:
490:
486:
482:
480:
467:
466:
456:
446:
445:
439:substitution
436:
432:
425:naphthalenes
418:
417:
397:
396:
390:
389:, hence are
387:carbocations
376:
361:
360:
351:
336:
321:
308:substitution
305:
301:
297:
289:
285:
273:
269:
258:
250:
246:
236:
228:
217:
213:
211:
205:
201:
193:
191:
184:-directors.
181:
165:
161:
143:
131:
125:
119:
118:
111:
105:
104:
97:
91:
90:
70:substitution
67:
63:
59:
45:substituents
36:are part of
30:
29:
926:pralidoxime
881:pralidoxime
579:naphthalene
408:calixarenes
239:in general.
47:other than
1616:Categories
955:References
796:, and the
744:resorcinol
709:, and the
707:resorcinol
563:Karl GrÀbe
463:chemistry.
423:occurs in
292:compounds.
188:Properties
134:toluidines
82:See also:
1442:Secondary
1364:isomerism
1276:isomerism
1244:Chirality
593:in 1879.
499:following
412:acridines
383:isopropyl
235:than the
140:Synthesis
1477:Catenane
1446:tertiary
1302:notation
1119:p. 1142.
933:See also
887:isomer.
871:, shown
861:nitrogen
857:pyridine
730:catechol
699:catechol
597:Examples
529:form of
404:benzylic
231:is more
150:hydroxyl
49:hydrogen
1435:, cyclo
1298:–
1179:-, and
800:isomer
792:isomer
784:isomer
713:isomer
705:isomer
697:isomer
671:-cresol
654:-cresol
637:-cresol
617:(OH)(CH
603:isomers
587:benzene
527:racemic
495:correct
477:Origins
261:isomer.
257:of the
208:isomers
174:nitrile
1591:Î-, Î-
1483:catena
1236:Topics
1100:- and
944:Isomer
899:niacin
883:is an
877:cation
869:niacin
788:, the
776:(COOH)
701:, the
607:cresol
503:beside
501:, and
489:, and
381:, and
379:-butyl
304:, and
178:ketone
176:, and
158:phenyl
156:, and
66:, and
1470:spiro
1340:ortho
1311:)-, (
1286:trans
1274:trans
1173:ortho
1094:ortho
1086:- et
1080:ortho
1036:IUPAC
1007:IUPAC
885:ortho
782:ortho
695:ortho
567:ortho
555:ortho
539:ortho
507:ortho
483:ortho
461:aryne
286:ortho
270:ortho
264:Many
259:ortho
251:ortho
233:polar
229:ortho
214:ortho
202:ortho
170:nitro
162:ortho
154:alkyl
146:amino
98:ortho
92:ortho
60:Ortho
32:Arene
1533:), (
1513:), (
1456:tert
1444:and
1392:anti
1370:endo
1358:Endo
1348:para
1344:meta
1181:para
1177:meta
1102:meta
1098:para
1088:mĂȘta
1084:para
873:meta
867:and
798:para
790:meta
711:para
703:meta
689:(OH)
621:):
575:para
571:meta
559:meta
547:para
545:and
543:meta
519:para
511:meta
491:para
487:meta
468:Tele
457:cine
447:cine
437:tele
435:and
433:Cine
419:Peri
410:and
398:Meso
391:ipso
377:tert
362:Ipso
352:peri
337:meso
322:ipso
306:peri
302:meso
298:Ipso
290:para
274:para
272:and
247:para
237:para
218:para
216:and
206:para
204:and
194:para
182:meta
166:para
132:The
126:para
120:para
112:meta
106:meta
68:para
64:meta
1573:-,
1454:-,
1452:sec
1433:neo
1429:iso
1410:mer
1406:fac
1388:syn
1374:exo
1372:,
1362:exo
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1330:-,
1284:-,
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1082:-,
1050:doi
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1021:doi
1019:".
879:of
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605:of
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288:or
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770:6
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683:6
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652:m
635:o
619:3
615:4
613:H
611:6
414:.
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