260:
27:
46:
60:
536:. Unlike most alkyl bromides, this compound, later named tropylium bromide, is water-soluble but insoluble in many organic solvents. It is purified by crystallization from hot ethanol. Reaction with aqueous silver nitrate immediately gave silver bromide, indicating labile bromide. Tropylium bromide was deduced to be a salt,
652:) as a consequence of its Lewis acidity: it first acts as a Lewis acid to form an adduct with water, which can then donate a proton to another molecule of water, therefore indirectly acting as an Arrhenius acid:
1284:
1245:
1437:
Kitaigorodskii, A. I.; Struchkov, Yu. T.; Khotsyanova, T. L.; Vol'pin, M. E.; Kursanov, D. N. (1960). "Crystal structures of tropylium perchlorate and iodide".
309:
1574:
1106:
1515:
1269:
470:(tropylidene) was first synthesized in 1881. Salts of the tropylium cation can be stable, even with nucleophiles of moderate strength e.g.,
1579:
274:
1402:
Balaban, Alexandru T.; Oniciu, Daniela C.; Katritzky, Alan R. (2004). "Aromaticity as a
Cornerstone of Heterocyclic Chemistry".
1564:
1329:
1472:
Lifshitz, Chava (1994). "Tropylium Ion
Formation from Toluene: Solution of an Old Problem in Organic Mass Spectrometry".
438:
1531:
Green, Malcolm L. H.; Ng, Dennis K. P. (1995). "Cycloheptatriene and -enyl
Complexes of the Early Transition Metals".
569:
and Knox in 1954 by analysis of its infrared and ultraviolet spectra. The ionic structures of tropylium perchlorate (
471:
423:
238:
1253:
566:
1105:
Many metal complexes of tropylium ion are known. One example is , which is prepared by hydride abstraction from
897:
882:
893:
483:
167:
649:
773:
1569:
629:
517:
763:
83:
52:
255:
777:
133:
66:
1196:
821:
The tropylium cation reacts with nucleophiles to form substituted cycloheptatrienes, for example:
502:
397:
382:
179:
1511:
1454:
1419:
1265:
759:
528:
In 1891 G. Merling obtained a water-soluble bromine-containing compound from the reaction of
199:
1540:
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1446:
1411:
1384:
1354:
1298:
1257:
1156:
886:
529:
467:
403:
332:
32:
1313:
A mixture of Cl and is produced by treatment of tropylidene with phosphorus pentachloride.
1333:
901:
143:
259:
1375:
Eggers
Doering, W. von; Knox, L. H. (1954). "The Cycloheptatrienylium (Tropylium) Ion".
432:
45:
1558:
776:. This fragment is often found for aromatic compounds containing a benzyl unit. Upon
1294:
632:. The bond length of the carbon-carbon bonds is longer (147 pm) than those of
225:
59:
1016:
1012:
738:
gives acidic aqueous solutions in much the same way.) The equilibrium constant is
636:(140 pm) but still shorter than those of a typical single-bonded species like
121:, Cyclohepta-2,4,6-trienylium, Cyclohepta-1,3,5-triene, 2,4,6-Cycloheptatrienylium
1250:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
1289:
747:
1358:
735:
363:
190:
1458:
1326:
1293:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1439:
Bulletin of the
Academy of Sciences of the USSR Division of Chemical Science
1302:
1423:
1261:
490:
459:
1544:
1485:
1388:
478:). Its bromide and chloride salts can be made from cycloheptatriene and
1450:
1325:
Organic
Syntheses, Coll. Vol. 5, p.1138 (1973); Vol. 43, p.101 (1963).
1123:
1118:
633:
533:
479:
463:
212:
1415:
26:
637:
506:
431:
Except where otherwise noted, data are given for materials in their
513:
510:
166:
156:
520:
in which each carbon atom carries part of the positive charge.
462:
species with a formula of . Its name derives from the molecule
417:
1510:(46th ed.). Krishna Prakashan Media. pp. 614–615.
243:
58:
44:
792:), which rearranges to the highly stable tropylium cation (
648:
The tropylium ion is an acid in aqueous solution (i.e., an
1212:
Chemical Names: Tropylium; Cycloheptatrienylium; Cyc-
1015:, the tropylium cation undergoes rearrangement into
1246:International Union of Pure and Applied Chemistry
224:
758:The tropylium ion is frequently encountered in
293:: InChI=1S/C7H7/c1-2-4-6-7-5-3-1/h1-7H/q+1
142:
1347:Berichte der Deutschen Chemischen Gesellschaft
516:. The structure shown is a composite of seven
493:, planar, cyclic ion. It has 6 π-electrons (4
8:
1151:
1149:
1147:
1145:
1143:
1141:
1139:
1011:When treated with oxidising agents such as
1501:
1499:
1497:
1495:
892:Reaction with a cyclopentadienide salt of
258:
198:
18:
1191:
1189:
1187:
1185:
1183:
1181:
902:7-cyclopentadienylcyclohepta-1,3,5-triene
746:, making it about as acidic in water as
283:InChI=1S/C7H7/c1-2-4-6-7-5-3-1/h1-7H/q+1
1135:
505:of aromaticity. It can coordinate as a
314:
279:
254:
1107:cycloheptatrienemolybdenum tricarbonyl
780:, the benzyl fragment forms a cation (
296:Key: OJOSABWCUVCSTQ-UHFFFAOYSA-N
286:Key: OJOSABWCUVCSTQ-UHFFFAOYSA-N
7:
1370:
1368:
1345:Merling, G. (1891). "Ueber Tropin".
215:
1575:Non-benzenoid aromatic carbocycles
1290:Compendium of Chemical Terminology
14:
501: = 1), which fulfills
25:
772: = 91 and is used in
435:(at 25 °C , 100 kPa).
1254:The Royal Society of Chemistry
1:
1474:Accounts of Chemical Research
1233:; Cyclohepta-2,4,6-trienylium
1580:Cycloheptatrienyl complexes
762:in the form of a signal at
472:tropylium tetrafluoroborate
424:Tropylium tetrafluoroborate
40:
1596:
1359:10.1002/cber.189102402151
883:lithium aluminium hydride
628:) have been confirmed by
429:
409:
375:
325:
305:
270:
126:
94:
82:
77:
39:
24:
1201:pubchem.ncbi.nlm.nih.gov
1157:"tropylium | ChemSpider"
599:) and tropylium iodide (
484:phosphorus pentachloride
456:cycloheptatrienyl cation
1303:10.1351/goldbook.M04002
474:and tropylium bromide (
1508:Reactions and Reagents
1506:O. P. Agarwai (2009).
774:mass spectrum analysis
518:resonance contributors
497: + 2, where
63:
49:
1565:Simple aromatic rings
1262:10.1039/9781849733069
630:X-ray crystallography
62:
48:
1323:Tropylium fluoborate
88:Cycloheptatrienylium
84:Preferred IUPAC name
53:ball-and-stick model
1545:10.1021/cr00034a006
1486:10.1021/ar00041a004
1389:10.1021/ja01641a027
371: g·mol
180:Beilstein Reference
67:space-filling model
21:
1451:10.1007/bf01178699
1332:2012-08-29 at the
1161:www.chemspider.com
439:Infobox references
410:Related compounds
64:
50:
19:
1517:978-81-87224-65-5
1416:10.1021/cr0306790
1383:(12): 3203–3206.
1271:978-0-85404-182-4
760:mass spectrometry
754:Mass spectrometry
447:Chemical compound
445:
444:
239:CompTox Dashboard
168:Interactive image
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72:
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1533:Chemical Reviews
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1410:(5): 2777–2812.
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1377:J. Am. Chem. Soc
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1353:(2): 3108–3126.
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1256:. p. 1127.
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887:cycloheptatriene
877:
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530:cycloheptatriene
489:It is a regular
486:, respectively.
468:cycloheptatriene
404:regular heptagon
370:
357:
356:
355:
347:
346:
333:Chemical formula
263:
262:
247:
245:
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33:skeletal formula
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640:(154 pm).
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1539:(2): 439–473.
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1480:(5): 138–144.
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650:Arrhenius acid
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1020:
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881:Reduction by
824:
823:
822:
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503:Hückel's rule
500:
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452:tropylium ion
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23:
1570:Carbocations
1536:
1532:
1526:
1507:
1477:
1473:
1467:
1445:(1): 32–36.
1442:
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1407:
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1211:
1204:. Retrieved
1200:
1172:
1165:. Retrieved
1160:
1104:
1017:benzaldehyde
1013:chromic acid
1010:
891:
880:
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764:
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527:
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451:
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127:Identifiers
97:
95:Other names
1206:30 December
1197:"Tropylium"
1167:30 December
748:acetic acid
466:from which
383:Point group
326:Properties
317:c1=cc=cc=c1
1559:Categories
1130:References
778:ionization
736:Boric acid
491:heptagonal
376:Structure
364:Molar mass
191:ChemSpider
155:3D model (
134:CAS Number
20:Tropylium
1459:0568-5230
1404:Chem. Rev
1173:tropylium
817:Reactions
676:+ 2
476:see below
144:4118-59-6
1424:15137807
1330:Archived
1295:molecule
1248:(2014).
1113:See also
460:aromatic
185:1902352
1124:Borepin
1119:Azulene
900:yields
898:lithium
885:yields
644:Acidity
634:benzene
567:Doering
534:bromine
524:History
480:bromine
464:tropine
358:
226:5224206
213:PubChem
200:4394444
1514:
1457:
1422:
1268:
894:sodium
638:ethane
507:ligand
458:is an
418:anions
416:Other
369:91.132
310:SMILES
229:
203:
78:Names
1285:IUPAC
565:, by
514:atoms
511:metal
275:InChI
157:JSmol
1512:ISBN
1455:ISSN
1420:PMID
1327:link
1266:ISBN
1208:2018
1169:2018
1045:HCrO
782:PhCH
532:and
450:The
1541:doi
1482:doi
1447:doi
1412:doi
1408:104
1385:doi
1355:doi
1299:doi
1297:".
1258:doi
1079:CrO
1075:CHO
1006:NaX
896:or
813:).
740:1.8
589:ClO
509:to
482:or
454:or
244:EPA
216:CID
98:cyc
16:Ion
1561::
1537:95
1535:.
1494:^
1478:27
1476:.
1453:.
1441:.
1418:.
1406:.
1381:76
1379:.
1367:^
1351:24
1349:.
1287:,
1264:.
1252:.
1210:.
1199:.
1180:^
1171:.
1159:.
1138:^
1109:.
1089:+
1077:+
1055:→
1043:+
1019::
1004:+
965:→
956:Na
936:+
904::
889:.
876:CN
856:→
847:CN
845:+
750:.
744:10
711:+
709:OH
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556:Br
390:7h
1547:.
1543::
1520:.
1488:.
1484::
1461:.
1449::
1443:9
1426:.
1414::
1391:.
1387::
1361:.
1357::
1301::
1274:.
1260::
1228:7
1223:H
1219:7
1214:C
1100:O
1096:2
1091:H
1084:2
1071:5
1066:H
1062:6
1057:C
1050:4
1038:7
1033:H
1029:7
1024:C
999:5
994:H
990:5
985:C
981:7
976:H
972:7
967:C
952:5
947:H
943:5
938:C
927:X
923:7
918:H
914:7
909:C
872:7
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863:7
858:C
840:7
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808:7
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799:7
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787:2
769:z
767:/
765:m
742:×
734:(
722:O
718:3
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705:7
700:H
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687:O
683:2
678:H
671:7
666:H
662:7
657:C
619:I
615:7
610:H
606:7
601:C
594:4
585:7
580:H
576:7
571:C
552:7
547:H
543:7
538:C
499:n
495:n
388:D
353:7
348:H
344:7
339:C
246:)
242:(
159:)
116:7
111:H
107:7
102:C
100:-
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