761:
687:
600:
583:
287:
816:
The aryl halides produced on the largest scale are chlorobenzene and the isomers of dichlorobenzene. One major but discontinued application was the use of chlorobenzene as a solvent for dispersing the herbicide Lasso. Overall, production of aryl chlorides (also naphthyl derivatives) has been
270:
derivatives. Arenes with electron donating groups react with halogens even in the absence of Lewis acids. For example, phenols and anilines react quickly with chlorine and bromine water to give multihalogenated products. Many detailed laboratory procedures are available. For alkylbenzene
525:
were used extensively from the 1930s to 1950s in cable and capacitor production, due to their insulating, hydrophobic, and flame retardant properties, but they have since been phased out for this use due to toxicity, environmental persistence, and introduction of new materials.
654:
Unlike in most other substitution reactions, fluoride is the best leaving group, and iodide the worst. A 2018 paper indicates that this situation may actually be rather common, occurring in systems that were previously assumed to proceed via
217:
Aryl chlorides are the aryl halides produced on the largest scale commercially: 150,000 tons/y in the US alone (1994). Production levels are decreasing owing to environmental concerns. Chlorobenzenes are used mainly as solvents.
47:
because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.
579:) catalyze the reactions. Numerous are derivatives of electron-rich rings found in tyrosine, tryptophan, and various pyrroles. Some of these natural aryl halides exhibit useful medicinal properties.
618:
The C-X distances for aryl halides follow the expected trend. These distances for fluorobenzene, chlorobenzene, bromobenzene, and methyl 4-iodobenzoate are 135.6(4), 173.90(23), 189.8(1), and 209.9
434:
This method is applicable to the preparation of all aryl halides. One limitation is that most, but not all, aryl lithium and
Grignard reagents are produced from aryl halides.
352:
568:
Many chlorinated and brominated aromatic compounds are produced by marine organisms. The chloride and bromide in ocean waters are the source of the halogens. Various
757:, by adding the magnesium to the aryl halide in an ethereal solution, works well if the aromatic ring is not significantly deactivated by electron-withdrawing groups.
772:
The halides can be displaced by strong nucleophiles via reactions involving radical anions. Alternatively aryl halides, especially the bromides and iodides, undergo
635:
Unlike typical alkyl halides, aryl halides typically do not participate in conventional substitution reactions. Aryl halides with electron-withdrawing groups in the
1159:
Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Pyridine and
Pyridine Derivatives".
1194:
Mondal, Santanu; Raja, Karuppusamy; Schweizer, Ulrich; Mugesh, Govindasamy (2016). "Chemistry and
Biology in the Biosynthesis and Action of Thyroid Hormones".
909:
Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine
Compounds, Organic".
279:
conditions, whereas ring halogenation is favored in the presence of Lewis acids. The decolouration of bromine water by electron-rich arenes is used in the
1132:
Snieckus, Victor (1990). "Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics".
1161:
911:
1532:
sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as sole carbon sources".
61:
Aryl fluorides are used as synthetic intermediates, e.g. for the preparation of pharmaceuticals, pesticides, and liquid crystals. The conversion of
457:
includes halogenated derivatives of any aromatic compound, it commonly refers to halobenzenes, which are specifically halogenated derivatives of
398:, but otherwise these compounds are not produced on a large scale. Aryl iodides are "easy" substrates for many reactions such as
1229:
Brito, Juan P.; Ross, Joseph S.; El Kawkgi, Omar M.; Maraka, Spyridoula; Deng, Yihong; Shah, Nilay D.; Lipska, Kasia J. (2021).
1382:
1056:
1584:
1178:
973:
928:
382:
can also be used to convert diazonium salts to bromobenzenes using using copper-based reagents. Owing to high cost of
1089:
998:
298:
of benzene has been well investigated, motivated by the avoidance of HCl as a coproduct in the direct halogenation:
339:
can also be used to convert diazonium salts to chlorobenzenes using copper-based reagents. Owing to high cost of
874:
Shimizu, Masaki; Hiyama, Tamejiro (2005). "Modern
Synthetic Methods for Fluorine-Substituted Target Molecules".
991:
Electrophilic
HalogenationReaction Pathways Involving Attack by Electrophilic Halogens on Unsaturated Compounds
777:
65:
is a well established route to aryl fluorides. Thus, anilines are precursors to aryl fluorides. In the classic
379:
409:
Aryl iodides can be prepared by treating diazonium salts with iodide salts. Electron-rich arenes such as
1611:
522:
481:
containing at least two different types of halogens bonded to the same benzene ring. There are also many
221:
956:
Beck, U.; Löser, E. (2011). "Chlorinated
Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons".
167:
710:
reaction, aryl halides are converted to aryl lithium compounds. Illustrative is the preparation of
1278:
399:
356:
406:, but they are much more expensive than the lighter, less reactive aryl chlorides and bromides.
1616:
800:
707:
482:
854:
360:
1576:
651:
reactions. For example, 2,4-dinitrochlorobenzene reacts in basic solution to give a phenol.
1476:
1411:
1339:
1330:
Gribble, Gordon W. (2004). "Natural
Organohalogens: A New Frontier for Medicinal Agents?".
395:
175:
171:
8:
1606:
1480:
1415:
1343:
1505:
1464:
1440:
1399:
1307:
1282:
1255:
1230:
818:
773:
760:
372:
336:
229:
66:
1463:
Jacobsen, Eric N.; Harrison A. Besser; Zeng, Yuwen; Kwan, Eugene E. (September 2018).
1580:
1549:
1510:
1492:
1445:
1427:
1378:
1312:
1260:
1211:
1174:
1085:
1052:
1020:
994:
969:
924:
891:
706:, to give organometallic derivatives that function as sources of aryl anions. By the
478:
70:
32:
20:
1246:
1572:
1541:
1500:
1484:
1435:
1419:
1370:
1347:
1302:
1294:
1250:
1242:
1203:
1166:
1141:
1114:
1077:
1029:
961:
916:
883:
754:
538:
417:
403:
1374:
1081:
805:
576:
535:
364:
295:
267:
1545:
1298:
853:
Aryl bromides are widely used as fire-retardants. The most prominent member is
719:
498:
466:
462:
383:
340:
62:
1488:
1365:
Oberhammer, Heinz (2009). "The
Structural Chemistry of Carbon-Halogen Bonds".
1600:
1496:
1431:
1170:
1118:
1033:
965:
920:
711:
605:
506:
502:
470:
233:
163:
1553:
1514:
1449:
1316:
1264:
1215:
1207:
895:
887:
715:
672:
558:
474:
280:
276:
375:
is poorly reactive toward bromine, necessitating the use of acidic media.
791:. At high temperatures, aryl groups react with ammonia to give anilines.
518:
448:
225:
1423:
1145:
1072:
Lyday, Phyllis A.; Kaiho, Tatsuo (2015). "Iodine and Iodine
Compounds".
1351:
686:
591:
587:
569:
162:
Many commercial aryl fluorides are produced from aryl chlorides by the
44:
1398:
Ritter, Tobias; Hooker, Jacob M.; Neumann, Constanze N. (June 2016).
703:
619:
546:
505:. Chloropyridines are important intermediates to pharmaceuticals and
232:, catalyze the reactions. The most abundantly produced aryl halide,
604:
The chemical structure of 6,6′-dibromoindigo, the main component of
494:
36:
1462:
1014:
Atkinson, Edward R.; Murphy, Donald M.; Lufkin, James E. (1951). "
817:
declining since the 1980s, in part due to environmental concerns.
286:
16:
Aromatic compounds containing Halogen atom(s) in place of Hydrogen
1400:"Concerted nucleophilic aromatic substitution with 19F− and 18F−"
1158:
908:
699:
680:
676:
668:
458:
410:
272:
599:
561:
by electrophilic iodination of tyrosine derivative. Synthetic T
1046:
988:
788:
784:
572:
368:
290:
Reaction between benzene and halogen to form an halogenobenzene
266:
Monochlorination of benzene is accompanied by formation of the
40:
1105:
Janssen, Donald E.; Wilson, C. V. (1956). "4-Iodoveratrole".
582:
565:
is one of the most heavily prescribed medicines in the U.S.
166:. The method is often used for aryl chlorides also bearing
1567:
Ioffe, D.; Kampf, A. (2002). "Bromine, Organic Compounds".
857:, which is prepared by direct bromination of the diphenol.
644:
442:
35:
in which one or more hydrogen atoms, directly bonded to an
1193:
437:
1228:
224:
or "direct chlorination" is the main synthesis route.
413:
and dimethoxy derivatives react directly with iodine.
1051:. Englewood Cliffs, N.J: Prentice Hall. p. 947.
51:
1013:
1397:
1231:"Levothyroxine Use in the United States, 2008-2018"
693:
343:, this method is reserved for specialty chlorides.
386:, this method is reserved for specialty bromides.
667:Aryl halides often react via the intermediacy of
493:Halopyridines are based on the aromatic compound
351:The main aryl bromides produced commercially are
1598:
275:, the alkyl positions tend to be halogenated by
1569:Kirk-Othmer Encyclopedia of Chemical Technology
1465:"Concerted nucleophilic aromatic substitutions"
594:, is an aryl chloride isolated from soil fungi.
1162:Ullmann's Encyclopedia of Industrial Chemistry
1074:Ullmann's Encyclopedia of Industrial Chemistry
958:Ullmann's Encyclopedia of Industrial Chemistry
912:Ullmann's Encyclopedia of Industrial Chemistry
367:. They are produced by direct bromination of
1277:
1104:
873:
1527:
332:This technology is not widely used however.
512:
420:react with iodine to give the aryl halide:
1566:
1364:
1071:
1047:Boyd, Robert W.; Morrison, Robert (1992).
698:Aryl halides react with metals, generally
124:In some cases, the fluoride salt is used:
1504:
1439:
1306:
1254:
955:
951:
949:
947:
945:
943:
941:
529:
1131:
989:Peter Bernard, David De la Mare (1976).
783:Chlorobenzene was once the precursor to
598:
581:
443:Halobenzenes and halobenzene derivatives
285:
1577:10.1002/0471238961.0218151325150606.a01
1329:
1283:"What's New in Enzymatic Halogenations"
1196:Angewandte Chemie International Edition
1040:
876:Angewandte Chemie International Edition
1599:
1367:PATai's Chemistry of Functional Groups
1018:-4,4′,6,6′-Tetrachlorodiphenic Acid".
938:
517:Halogenated naphthalenes are based on
438:Classification according to aryl group
1528:Rehfuss, Marc; Urban, James (2005). "
787:, which is now made by oxidation of
613:
553:) are aryl iodides. A tetraiodide, T
170:. Illustrative is the synthesis of
1534:Systematic and Applied Microbiology
1287:Current Opinion in Chemical Biology
394:Synthetic aryl iodides are used as
13:
767:
759:
685:
52:Classification according to halide
14:
1628:
794:
461:. Groups of halobenzenes include
212:
56:
1281:; Walsh, Christopher T. (2007).
821:is produced from chlorobenzene:
694:Organometallic reagent formation
488:
346:
43:. Haloarenes are different from
1560:
1521:
1456:
1391:
1358:
1323:
1271:
1247:10.1001/jamainternmed.2021.2686
1222:
1187:
1152:
811:
630:
389:
363:. These materials are used as
1125:
1098:
1065:
1007:
993:. Cambridge University Press.
982:
902:
867:
1:
1375:10.1002/9780470682531.pat0002
1332:Journal of Chemical Education
1082:10.1002/14356007.a14_381.pub2
860:
804:is a bacterium that degrades
236:, is produced by this route:
625:
523:Polychlorinated naphthalenes
353:tetrabromophthalic anhydride
7:
1546:10.1016/j.syapm.2005.05.011
222:Friedel-Crafts halogenation
168:electron-withdrawing groups
10:
1633:
1299:10.1016/j.cbpa.2007.08.002
778:Buchwald–Hartwig amination
776:, and thus are subject to
662:
446:
1489:10.1038/s41557-018-0079-7
1279:Fujimori, Danica Galonić
1171:10.1002/14356007.a22_399
1119:10.15227/orgsyn.036.0046
1034:10.15227/orgsyn.031.0096
966:10.1002/14356007.o06_o03
921:10.1002/14356007.a11_349
808:as sole carbon sources.
513:Halogenated naphthalenes
400:cross-coupling reactions
1165:. Weinheim: Wiley-VCH.
915:. Weinheim: Wiley-VCH.
643:positions, can undergo
483:halobenzene derivatives
357:decabromodiphenyl ether
73:is the fluoride donor:
39:ring are replaced by a
1530:Rhodococcus phenolicus
1235:JAMA Internal Medicine
1208:10.1002/anie.201601116
888:10.1002/anie.200460441
801:Rhodococcus phenolicus
764:
708:metal-halogen exchange
690:
610:
596:
530:Aryl halides in nature
416:Aryl lithium and aryl
291:
855:tetrabromobisphenol-A
763:
689:
602:
585:
396:X-ray contrast agents
361:tetrabromobisphenol-A
289:
753:Direct formation of
671:. Chlorobenzene and
176:2-nitrochlorobenzene
172:2-fluoronitrobenzene
1481:2018NatCh..10..917K
1424:10.1038/nature17667
1416:2016Natur.534..369N
1344:2004JChEd..81.1441G
1146:10.1021/cr00104a001
1612:Aromatic compounds
1352:10.1021/ed081p1441
819:Triphenylphosphine
774:oxidative addition
765:
691:
611:
597:
479:mixed halobenzenes
453:Although the term
402:and conversion to
380:Gatterman reaction
373:Phthalic anhydride
371:and aryl ethers.
337:Gatterman reaction
292:
271:derivatives, e.g.
230:iron(III) chloride
67:Schiemann reaction
1410:(7607): 369–373.
1384:978-0-470-68253-1
1241:(10): 1402–1405.
1202:(27): 7606–7630.
1107:Organic Syntheses
1076:. pp. 1–13.
1058:978-0-13-643669-0
1049:Organic chemistry
1021:Organic Syntheses
780:-type reactions.
755:Grignard reagents
683:by this pathway.
614:Structural trends
418:Grignard reagents
404:Grignard reagents
195:Cl + KF → O
71:tetrafluoroborate
33:aromatic compound
21:organic chemistry
1624:
1591:
1590:
1564:
1558:
1557:
1525:
1519:
1518:
1508:
1469:Nature Chemistry
1460:
1454:
1453:
1443:
1395:
1389:
1388:
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1355:
1327:
1321:
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1226:
1220:
1219:
1191:
1185:
1184:
1156:
1150:
1149:
1134:Chemical Reviews
1129:
1123:
1122:
1102:
1096:
1095:
1069:
1063:
1062:
1044:
1038:
1036:
1011:
1005:
1004:
986:
980:
979:
953:
936:
934:
906:
900:
899:
871:
675:react in liquid
622:, respectively.
539:triiodothyronine
536:thyroid hormones
497:. This includes
430:
365:flame retardants
328:
262:
208:
158:
145:
144:
141:
120:
103:
102:
99:
94:
93:
90:
1632:
1631:
1627:
1626:
1625:
1623:
1622:
1621:
1597:
1596:
1595:
1594:
1587:
1565:
1561:
1526:
1522:
1461:
1457:
1396:
1392:
1385:
1363:
1359:
1328:
1324:
1276:
1272:
1227:
1223:
1192:
1188:
1181:
1157:
1153:
1130:
1126:
1103:
1099:
1092:
1070:
1066:
1059:
1045:
1041:
1012:
1008:
1001:
987:
983:
976:
954:
939:
931:
907:
903:
872:
868:
863:
848:
844:
840:
836:
832:
828:
814:
806:dichlorobenzene
797:
770:
768:Other reactions
748:
744:
740:
736:
696:
665:
659:Ar mechanisms.
658:
648:
633:
628:
616:
609:
595:
590:, an important
577:bromoperoxidase
564:
556:
552:
544:
532:
515:
499:chloropyridines
491:
451:
445:
440:
429:→ ArI + LiI
428:
424:
392:
384:diazonium salts
349:
341:diazonium salts
326:
322:
318:
314:
310:
306:
302:
296:oxychlorination
268:dichlorobenzene
260:
256:
252:
248:
244:
240:
215:
206:
202:
198:
194:
190:
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182:
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132:
128:
119:
115:
111:
107:
100:
97:
96:
91:
88:
87:
85:
81:
77:
63:diazonium salts
59:
54:
27:(also known as
17:
12:
11:
5:
1630:
1620:
1619:
1614:
1609:
1593:
1592:
1586:978-0471238966
1585:
1559:
1540:(8): 695–701.
1520:
1475:(9): 917–923.
1455:
1390:
1383:
1357:
1322:
1270:
1221:
1186:
1180:978-3527306732
1179:
1151:
1140:(6): 879–933.
1124:
1097:
1090:
1064:
1057:
1039:
1006:
999:
981:
975:978-3527306732
974:
937:
930:978-3527306732
929:
901:
882:(2): 214–231.
865:
864:
862:
859:
851:
850:
846:
842:
838:
834:
830:
826:
813:
810:
796:
795:Biodegradation
793:
769:
766:
751:
750:
746:
742:
738:
734:
695:
692:
664:
661:
656:
646:
632:
629:
627:
624:
615:
612:
603:
586:
562:
559:biosynthesised
554:
550:
542:
531:
528:
514:
511:
503:bromopyridines
490:
487:
467:chlorobenzenes
463:fluorobenzenes
447:Main article:
444:
441:
439:
436:
432:
431:
426:
391:
388:
348:
345:
330:
329:
324:
320:
316:
312:
311:+ 4 HCl + O
308:
304:
264:
263:
258:
254:
250:
246:
242:
214:
213:Aryl chlorides
211:
210:
209:
204:
200:
196:
192:
188:
184:
160:
159:
155:
151:
147:
134:
130:
122:
121:
117:
113:
109:
105:
83:
79:
58:
57:Aryl fluorides
55:
53:
50:
15:
9:
6:
4:
3:
2:
1629:
1618:
1617:Organohalides
1615:
1613:
1610:
1608:
1605:
1604:
1602:
1588:
1582:
1578:
1574:
1570:
1563:
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1349:
1345:
1341:
1337:
1333:
1326:
1318:
1314:
1309:
1304:
1300:
1296:
1293:(5): 553–60.
1292:
1288:
1284:
1280:
1274:
1266:
1262:
1257:
1252:
1248:
1244:
1240:
1236:
1232:
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1213:
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1201:
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1182:
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1101:
1093:
1091:9783527306732
1087:
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1027:
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1002:
1000:9780521290142
996:
992:
985:
977:
971:
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950:
948:
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824:
823:
822:
820:
809:
807:
803:
802:
792:
790:
786:
781:
779:
775:
762:
758:
756:
741:Br + BuLi → C
732:
731:
730:
728:
724:
723:-butyllithium
722:
717:
713:
712:phenyllithium
709:
705:
701:
688:
684:
682:
678:
674:
670:
660:
652:
650:
642:
638:
623:
621:
607:
606:Tyrian Purple
601:
593:
589:
584:
580:
578:
574:
571:
566:
560:
548:
540:
537:
527:
524:
520:
510:
508:
507:agrochemicals
504:
500:
496:
489:Halopyridines
486:
484:
480:
477:, as well as
476:
472:
471:bromobenzenes
468:
464:
460:
456:
450:
435:
423:
422:
421:
419:
414:
412:
407:
405:
401:
397:
387:
385:
381:
376:
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370:
366:
362:
358:
354:
347:Aryl bromides
344:
342:
338:
333:
301:
300:
299:
297:
288:
284:
282:
278:
274:
269:
239:
238:
237:
235:
234:chlorobenzene
231:
227:
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219:
181:
180:
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177:
173:
169:
165:
164:Halex process
127:
126:
125:
76:
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68:
64:
49:
46:
42:
38:
34:
30:
26:
22:
1568:
1562:
1537:
1533:
1529:
1523:
1472:
1468:
1458:
1407:
1403:
1393:
1366:
1360:
1338:(10): 1441.
1335:
1331:
1325:
1290:
1286:
1273:
1238:
1234:
1224:
1199:
1195:
1189:
1160:
1154:
1137:
1133:
1127:
1110:
1106:
1100:
1073:
1067:
1048:
1042:
1025:
1019:
1015:
1009:
990:
984:
957:
910:
904:
879:
875:
869:
852:
837:+ 6 Na → P(C
815:
812:Applications
799:
798:
782:
771:
752:
726:
720:
716:bromobenzene
697:
673:sodium amide
666:
653:
640:
636:
634:
631:Substitution
617:
567:
533:
516:
492:
475:iodobenzenes
454:
452:
433:
415:
408:
393:
390:Aryl iodides
377:
350:
334:
331:
293:
281:bromine test
277:free radical
265:
220:
216:
161:
123:
60:
28:
24:
18:
749:Li + BuBr
519:naphthalene
455:aryl halide
449:Halobenzene
226:Lewis acids
45:haloalkanes
25:aryl halide
1607:Haloarenes
1601:Categories
861:References
592:antibiotic
588:Vancomycin
570:peroxidase
425:ArLi + I
261:Cl + HCl
1497:1755-4349
1432:1476-4687
704:magnesium
626:Reactions
547:thyroxine
207:F + KCl
146:]F → C
29:haloarene
1554:16261859
1515:30013193
1450:27281221
1317:17881282
1265:34152370
1216:27226395
896:15614922
849:+ 6 NaCl
833:Cl + PCl
729:-BuLi):
679:to give
669:benzynes
495:pyridine
411:anilines
323:Cl + H
37:aromatic
31:) is an
1506:6105541
1477:Bibcode
1441:4911285
1412:Bibcode
1340:Bibcode
1308:2151916
1256:8218227
700:lithium
681:aniline
677:ammonia
663:Benzyne
575:(e.g.,
573:enzymes
459:benzene
369:phenols
315:→ 4 C
273:toluene
228:, e.g.
154:F + N
112:F + N
1583:
1552:
1513:
1503:
1495:
1448:
1438:
1430:
1404:Nature
1381:
1315:
1305:
1263:
1253:
1214:
1177:
1113:: 46.
1088:
1055:
1028:: 96.
997:
972:
927:
894:
789:cumene
785:phenol
718:using
545:) and
473:, and
359:, and
129:[C
78:[C
41:halide
714:from
637:ortho
253:→ C
249:+ Cl
174:from
116:+ BF
104:→ C
23:, an
1581:ISBN
1550:PMID
1511:PMID
1493:ISSN
1446:PMID
1428:ISSN
1379:ISBN
1313:PMID
1261:PMID
1212:PMID
1175:ISBN
1086:ISBN
1053:ISBN
995:ISBN
970:ISBN
925:ISBN
892:PMID
641:para
639:and
534:The
501:and
378:The
335:The
294:The
1573:doi
1542:doi
1501:PMC
1485:doi
1436:PMC
1420:doi
1408:534
1371:doi
1348:doi
1303:PMC
1295:doi
1251:PMC
1243:doi
1239:181
1204:doi
1167:doi
1142:doi
1115:doi
1078:doi
1030:doi
962:doi
917:doi
884:doi
825:3 C
702:or
557:is
303:4 C
95:]BF
19:In
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1233:.
1210:.
1200:55
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1173:.
1138:90
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1111:36
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1084:.
1026:31
1024:.
1016:dl
968:.
960:.
940:^
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880:44
878:.
649:Ar
620:pm
549:(T
541:(T
521:.
509:.
485:.
469:,
465:,
355:,
283:.
199:NC
187:NC
178::
69:,
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1575::
1556:.
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1517:.
1487::
1479::
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1061:.
1037:.
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978:.
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933:.
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898:.
886::
847:3
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843:5
841:H
839:6
835:3
831:5
829:H
827:6
747:5
745:H
743:6
739:5
737:H
735:6
733:C
727:n
725:(
721:n
657:N
655:S
647:N
645:S
608:.
563:4
555:4
551:4
543:3
427:2
327:O
325:2
321:5
319:H
317:6
313:2
309:6
307:H
305:6
259:5
257:H
255:6
251:2
247:6
245:H
243:6
241:C
205:4
203:H
201:6
197:2
193:4
191:H
189:6
185:2
183:O
156:2
152:5
150:H
148:6
143:2
140:+
137:N
135:5
133:H
131:6
118:3
114:2
110:5
108:H
106:6
101:4
98:−
92:2
89:+
86:N
84:5
82:H
80:6
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