591:
27:
316:
677:
Yonedo S, Shibata M, Kida S, Yoshida Zi, Kai Y, Miki K, Kasai N (January 1984). "A Novel
Aromatic Hydrocarbon with 16 π-Electron Periphery: "Cyclic Bicalicene"".
621:π electrons). Instead, however, the structure has a dominant partially-delocalized charge-separated structure consisting of four independently-
643:-Bicalicene, by contrast, is an antiaromatic hydrocarbon. A resonance structure with four aromatic rings, analogous to the one that makes the
442:
213:
1226:
1216:
378:
99:
417:
178:
508:
293:
1231:
809:
606:
800:
155:
1118:
747:
Jelena Đurđević Nikolić; Ivan Gutman (2016). "A Comparative Study of the Two
Isomers of Bicalicene".
187:
InChI=1S/C16H8/c1-3-9-10(4-1)14-8-16(14)12-6-2-5-11(12)15-7-13(9)15/h1-8H/b13-9-,14-10-,15-11-,16-12-
647:
isomer stable, would suffer from destabilizing charge effects, and other resonance structures have 4
197:
InChI=1/C16H8/c1-3-9-10(4-1)14-8-16(14)12-6-2-5-11(12)15-7-13(9)15/h1-8H/b13-9-,14-10-,15-11-,16-12-
951:
1221:
634:
575:
1012:
1007:
328:
119:
39:
354:
997:
992:
987:
982:
905:
713:
630:
164:
75:
8:
935:
579:
524:
344:
65:
717:
610:
609:, which is unusual for a 16 π electron ring system. Viewed as a unified ring structure,
1053:
793:
764:
403:
1114:
890:
729:
590:
768:
144:
1104:
900:
895:
778:
756:
721:
704:
Oziminski WP, Palusia M (2013). "Capturing the elusive aromaticity of bicalicene".
686:
531:
465:
236:
760:
543:
1154:
1149:
1063:
1032:
966:
961:
854:
502:
287:
1210:
786:
614:
271:
1099:
1048:
930:
915:
874:
849:
733:
690:
547:
1073:
1058:
956:
833:
622:
550:
rings linked into a larger eight-membered ring. There are two isomers:
527:
426:
InChI=1S/C16H8/c1-3-9-10-4-2-6-12(10)14-8-16(14)15-7-13(15)11(9)5-1/h1-8H
971:
859:
725:
487:
258:
110:
1195:
1185:
1180:
1109:
1017:
925:
869:
501:
Except where otherwise noted, data are given for materials in their
286:
Except where otherwise noted, data are given for materials in their
1190:
1144:
1134:
1124:
1094:
1078:
1068:
1022:
910:
864:
823:
559:
26:
746:
377:
98:
1159:
1139:
1129:
828:
390:
315:
131:
1027:
920:
1175:
367:
88:
676:
808:
679:Angewandte Chemie International Edition in English
1208:
703:
402:
143:
570:Bicalicene is prepared by treatment of 1,2-bis(
353:
74:
578:, followed by desulfurizing stannylation with
794:
697:
672:
670:
668:
801:
787:
665:
574:-butylthio)-3,3-dichlorocyclopropene with
118:
163:
589:
1209:
582:, and then treatment with silica gel.
782:
655:+2 π electrons in at least one ring.
429:Key: MIGVZWUAYKWALJ-UHFFFAOYSA-N
190:Key: FVDGMBFXSFSQOU-NONDJZLBSA-N
706:Physical Chemistry Chemical Physics
393:
332:Dicyclopentadicyclopropacyclooctene
200:Key: FVDGMBFXSFSQOU-NONDJZLBBM
134:
53:Dicyclopentadicyclopropacyclooctene
13:
1227:Non-benzenoid aromatic carbocycles
633:(two π electrons each) and two as
450:C1=CC2=C3C=C3C4=CC4=C5C=CC=C5C2=C1
277:
221:C1=CC2=C3C=C3C4=CC=CC4=C5C=C5C2=C1
51:)-Dicyclopentadicyclopropaannulene
14:
1243:
1217:Polycyclic aromatic hydrocarbons
810:Polycyclic aromatic hydrocarbons
477:
314:
248:
25:
607:polycyclic aromatic hydrocarbon
558:-bicalicene. It is a dimer of
505:(at 25 °C , 100 kPa).
290:(at 25 °C , 100 kPa).
740:
471:
242:
1:
761:10.1080/10406638.2016.1140659
749:Polycyclic Aromatic Compounds
658:
629:+2 π electron) rings: two as
585:
565:
7:
594:The four aromatic rings of
10:
1248:
1168:
1087:
1041:
944:
883:
842:
816:
499:
458:
438:
413:
337:
327:
322:
313:
284:
229:
209:
174:
58:
38:
33:
24:
976:-Benzopyrene(Olympicene)
637:(six π electrons each).
635:cyclopentadienyl anions
1232:Antiaromatic compounds
691:10.1002/anie.198400631
599:
952:Benzacephenanthrylene
631:cyclopropenyl cations
613:predicts it would be
593:
576:cyclopentadiene anion
936:Tricyclobutabenzene
718:2013PCCP...15.3286O
580:tributyltin hydride
495: g·mol
310:
266: g·mol
21:
726:10.1039/C2CP43426A
600:
542:, composed of two
509:Infobox references
305:
294:Infobox references
16:
1204:
1203:
1115:Hexabenzocoronene
998:Benzofluoranthene
993:Benzofluoranthene
988:Benzofluoranthene
983:Benzofluoranthene
906:Benzophenanthrene
554:-bicalicene and
517:Chemical compound
515:
514:
379:Interactive image
302:Chemical compound
300:
299:
276:125–130 °C (
100:Interactive image
1239:
1105:Diindenoperylene
1013:Dibenzanthracene
1008:Dibenzanthracene
1003:trans-Bicalicene
803:
796:
789:
780:
779:
773:
772:
744:
738:
737:
712:(9): 3286–3293.
701:
695:
694:
674:
532:chemical formula
494:
479:
473:
466:Chemical formula
406:
395:
381:
357:
318:
311:
304:
279:
265:
250:
244:
237:Chemical formula
167:
147:
136:
122:
102:
78:
29:
22:
15:
1247:
1246:
1242:
1241:
1240:
1238:
1237:
1236:
1207:
1206:
1205:
1200:
1169:General classes
1164:
1083:
1037:
940:
879:
838:
812:
807:
777:
776:
745:
741:
702:
698:
675:
666:
661:
605:-Bicalicene is
588:
568:
544:cyclopentadiene
541:
537:
518:
511:
506:
492:
482:
476:
468:
454:
451:
446:
445:
434:
431:
430:
427:
421:
420:
409:
396:
384:
371:
360:
347:
333:
303:
296:
291:
263:
253:
247:
239:
225:
222:
217:
216:
205:
202:
201:
198:
192:
191:
188:
182:
181:
170:
150:
137:
125:
105:
92:
81:
68:
54:
52:
12:
11:
5:
1245:
1235:
1234:
1229:
1224:
1219:
1202:
1201:
1199:
1198:
1193:
1188:
1183:
1178:
1172:
1170:
1166:
1165:
1163:
1162:
1157:
1155:Trinaphthylene
1152:
1150:Superphenalene
1147:
1142:
1137:
1132:
1127:
1122:
1112:
1107:
1102:
1097:
1091:
1089:
1085:
1084:
1082:
1081:
1076:
1071:
1066:
1064:Dibenzopyrenes
1061:
1056:
1051:
1045:
1043:
1039:
1038:
1036:
1035:
1033:Tetraphenylene
1030:
1025:
1020:
1015:
1010:
1005:
1000:
995:
990:
985:
980:
979:
978:
969:
964:
954:
948:
946:
942:
941:
939:
938:
933:
928:
923:
918:
913:
908:
903:
898:
893:
891:Benzanthracene
887:
885:
881:
880:
878:
877:
872:
867:
862:
857:
855:Acenaphthylene
852:
846:
844:
840:
839:
837:
836:
831:
826:
820:
818:
814:
813:
806:
805:
798:
791:
783:
775:
774:
739:
696:
663:
662:
660:
657:
587:
584:
567:
564:
539:
535:
516:
513:
512:
507:
503:standard state
500:
497:
496:
490:
484:
483:
480:
474:
469:
464:
461:
460:
456:
455:
453:
452:
449:
441:
440:
439:
436:
435:
433:
432:
428:
425:
424:
416:
415:
414:
411:
410:
408:
407:
399:
397:
389:
386:
385:
383:
382:
374:
372:
365:
362:
361:
359:
358:
350:
348:
343:
340:
339:
335:
334:
331:
325:
324:
320:
319:
301:
298:
297:
292:
288:standard state
285:
282:
281:
274:
268:
267:
261:
255:
254:
251:
245:
240:
235:
232:
231:
227:
226:
224:
223:
220:
212:
211:
210:
207:
206:
204:
203:
199:
196:
195:
193:
189:
186:
185:
177:
176:
175:
172:
171:
169:
168:
160:
158:
152:
151:
149:
148:
140:
138:
130:
127:
126:
124:
123:
115:
113:
107:
106:
104:
103:
95:
93:
86:
83:
82:
80:
79:
71:
69:
64:
61:
60:
56:
55:
42:
36:
35:
31:
30:
9:
6:
4:
3:
2:
1244:
1233:
1230:
1228:
1225:
1223:
1222:Cyclopropenes
1220:
1218:
1215:
1214:
1212:
1197:
1194:
1192:
1189:
1187:
1184:
1182:
1179:
1177:
1174:
1173:
1171:
1167:
1161:
1158:
1156:
1153:
1151:
1148:
1146:
1143:
1141:
1138:
1136:
1133:
1131:
1128:
1126:
1123:
1120:
1116:
1113:
1111:
1108:
1106:
1103:
1101:
1098:
1096:
1093:
1092:
1090:
1086:
1080:
1077:
1075:
1072:
1070:
1067:
1065:
1062:
1060:
1057:
1055:
1054:Benzoperylene
1052:
1050:
1047:
1046:
1044:
1040:
1034:
1031:
1029:
1026:
1024:
1021:
1019:
1016:
1014:
1011:
1009:
1006:
1004:
1001:
999:
996:
994:
991:
989:
986:
984:
981:
977:
975:
970:
968:
965:
963:
960:
959:
958:
955:
953:
950:
949:
947:
943:
937:
934:
932:
929:
927:
924:
922:
919:
917:
914:
912:
909:
907:
904:
902:
901:Benzofluorene
899:
897:
896:Benzofluorene
894:
892:
889:
888:
886:
882:
876:
873:
871:
868:
866:
863:
861:
858:
856:
853:
851:
848:
847:
845:
841:
835:
832:
830:
827:
825:
822:
821:
819:
815:
811:
804:
799:
797:
792:
790:
785:
784:
781:
770:
766:
762:
758:
754:
750:
743:
735:
731:
727:
723:
719:
715:
711:
707:
700:
692:
688:
684:
680:
673:
671:
669:
664:
656:
654:
651:rather than 4
650:
646:
642:
638:
636:
632:
628:
624:
620:
616:
615:anti-aromatic
612:
611:Hückel's rule
608:
604:
597:
592:
583:
581:
577:
573:
563:
561:
557:
553:
549:
545:
533:
529:
526:
522:
510:
504:
498:
491:
489:
486:
485:
470:
467:
463:
462:
457:
448:
447:
444:
437:
423:
422:
419:
412:
405:
401:
400:
398:
392:
388:
387:
380:
376:
375:
373:
369:
364:
363:
356:
352:
351:
349:
346:
342:
341:
336:
330:
326:
321:
317:
312:
308:
295:
289:
283:
275:
273:
272:Melting point
270:
269:
262:
260:
257:
256:
241:
238:
234:
233:
228:
219:
218:
215:
208:
194:
184:
183:
180:
173:
166:
162:
161:
159:
157:
154:
153:
146:
142:
141:
139:
133:
129:
128:
121:
117:
116:
114:
112:
109:
108:
101:
97:
96:
94:
90:
85:
84:
77:
73:
72:
70:
67:
63:
62:
57:
50:
46:
41:
37:
32:
28:
23:
19:
1100:Dicoronylene
1049:Anthanthrene
1002:
973:
931:Triphenylene
916:Fluoranthene
875:Phenanthrene
850:Acenaphthene
752:
748:
742:
709:
705:
699:
685:(1): 63–64.
682:
678:
652:
648:
644:
640:
639:
626:
618:
602:
601:
595:
571:
569:
555:
551:
548:cyclopropene
520:
519:
338:Identifiers
309:-Bicalicene
306:
59:Identifiers
48:
44:
20:-Bicalicene
17:
1074:Triangulene
1059:Corannulene
967:Benzopyrene
962:Benzopyrene
957:Benzopyrene
834:Naphthalene
598:-bicalicene
528:hydrocarbon
459:Properties
355:122605-73-6
230:Properties
40:IUPAC names
1211:Categories
1119:Hexa-cata-
860:Anthracene
659:References
586:Properties
525:polycyclic
521:Bicalicene
488:Molar mass
366:3D model (
345:CAS Number
329:IUPAC name
259:Molar mass
165:494N9YP93C
111:ChemSpider
87:3D model (
76:73091-52-8
66:CAS Number
1196:Phenacene
1186:Cyclacene
1181:Circulene
1110:Heptacene
1018:Pentacene
926:Tetracene
870:Phenalene
566:Synthesis
404:101619525
1191:Helicene
1145:Sumanene
1135:Rubicene
1125:Kekulene
1095:Coronene
1088:7+ rings
1079:Zethrene
1069:Hexacene
1023:Perylene
911:Chrysene
865:Fluorene
824:Butalene
769:99213944
734:23358331
623:aromatic
560:calicene
546:and two
1160:Truxene
1140:Rubrene
1130:Ovalene
1042:6 rings
945:5 rings
884:4 rings
843:3 rings
829:Azulene
817:2 rings
755:: 1–7.
714:Bibcode
493:200.240
391:PubChem
264:200.240
145:5257656
132:PubChem
120:4423214
1028:Picene
921:Pyrene
767:
732:
443:SMILES
323:Names
214:SMILES
34:Names
1176:Acene
765:S2CID
645:trans
603:trans
596:trans
556:trans
530:with
418:InChI
368:JSmol
179:InChI
89:JSmol
18:trans
730:PMID
572:tert
156:UNII
757:doi
722:doi
687:doi
641:cis
552:cis
523:is
394:CID
307:cis
278:dec
135:CID
47:,8a
43:(4a
1213::
763:.
753:38
751:.
728:.
720:.
710:15
708:.
683:23
681:.
667:^
625:(4
617:(4
562:.
536:16
475:16
280:)
246:16
1121:)
1117:(
974:H
972:6
802:e
795:t
788:v
771:.
759::
736:.
724::
716::
693:.
689::
653:n
649:n
627:n
619:n
540:8
538:H
534:C
481:8
478:H
472:C
370:)
252:8
249:H
243:C
91:)
49:Z
45:Z
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