198:
400:
51:
42:
482:
406:
399:
247:
671:
644:
587:
212:
17:
320:
676:
457:
577:
176:
516:
193:
495:
475:
469:
391:
379:
119:
501:
546:
139:
69:
456:
relative to many carbon acids. The enhanced acidity is attributed to stabilization of the
443:
95:
197:
8:
85:
431:
640:
583:
164:
615:
270:
603:
666:
449:
415:
363:
305:
314:
300:
660:
371:
50:
573:
435:
41:
481:
290:
130:
620:
439:
333:
313:
Except where otherwise noted, data are given for materials in their
604:"Noncomparative scaling of aromaticity through electron itinerancy"
419:
345:
118:
151:
579:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
367:
571:
375:
108:
602:
Paul, Satadal; Goswami, Tamal; Misra, Anirban (2015-10-01).
181:
453:
582:(6th ed.), New York: Wiley-Interscience, p. 66,
409:Resonance structures of the cyclopentadienyl anion
658:
634:
601:
539:
163:
553:. National Center for Biotechnology Information
94:
385:
485:Metallocene structure where "M" is a metal
474:Cyclopentadienyl anions form a variety of
196:
138:
619:
480:
414:The cyclopentadienyl anion is a planar,
362:. It is formed by the deprotonation of
192:
14:
659:
224:Key: SINKOGOPEQSHQD-UHFFFAOYSA-N
221:InChI=1S/C5H5/c1-2-4-5-3-1/h1-5H/q-1
234:Key: SINKOGOPEQSHQD-UHFFFAOYAD
231:InChI=1/C5H5/c1-2-4-5-3-1/h1-5H/q-1
154:
24:
672:Non-benzenoid aromatic carbocycles
442:provides 2 π-electrons, which are
366:. The cyclopentadienyl anion is a
49:
40:
25:
688:
430: = 1), which fulfills
398:
317:(at 25 °C , 100 kPa).
628:
595:
565:
13:
1:
532:
452:has a pKa of about 16. It is
422:ion; it has 6 π-electrons (4
7:
489:
36:
10:
693:
476:cyclopentadienyl complexes
467:
460:, cyclopentadienyl anion.
389:
348:species with a formula of
635:C. Elschenbroich (2006).
551:PubChem Compound Database
517:Cyclooctatetraenide anion
463:
386:Resonance and aromaticity
311:
295:65.09 g/mol
263:
243:
208:
78:
68:
63:
35:
496:Cyclopentadienyl radical
470:Cyclopentadienyl complex
392:Sodium cyclopentadienide
380:organometallic chemistry
502:Cyclopentadienyl cation
31:Cyclopentadienyl anion
486:
426: + 2, where
338:cyclopentadienyl anion
54:
45:
27:Aromatic ionic species
677:Simple aromatic rings
484:
434:of aromaticity. Each
53:
44:
572:Smith, Michael B.;
547:"Cyclopentadienide"
358:and abbreviated as
32:
487:
321:Infobox references
55:
46:
30:
646:978-3-527-29390-2
621:10.1063/1.4933191
589:978-0-471-72091-1
342:cyclopentadienide
329:Chemical compound
327:
326:
177:CompTox Dashboard
120:Interactive image
73:Cyclopentadienide
59:
58:
18:Cyclopentadienide
16:(Redirected from
684:
651:
650:
632:
626:
625:
623:
599:
593:
592:
569:
563:
562:
560:
558:
543:
528:
527:
526:
513:
512:
511:
446:into the ring.
402:
357:
356:
355:
284:
283:
282:
271:Chemical formula
201:
200:
185:
183:
167:
156:
142:
122:
98:
37:
33:
29:
21:
692:
691:
687:
686:
685:
683:
682:
681:
657:
656:
655:
654:
647:
637:Organometallics
633:
629:
600:
596:
590:
570:
566:
556:
554:
545:
544:
540:
535:
525:
523:
522:
521:
520:
510:
508:
507:
506:
505:
492:
472:
466:
450:Cyclopentadiene
412:
411:
410:
408:
403:
394:
388:
364:cyclopentadiene
354:
352:
351:
350:
349:
330:
323:
318:
306:Cyclopentadiene
281:
279:
278:
277:
276:
273:
259:
256:
251:
250:
239:
236:
235:
232:
226:
225:
222:
216:
215:
204:
194:DTXSID601027108
186:
179:
170:
157:
145:
125:
112:
101:
88:
74:
28:
23:
22:
15:
12:
11:
5:
690:
680:
679:
674:
669:
653:
652:
645:
627:
614:(10): 107211.
594:
588:
564:
537:
536:
534:
531:
530:
529:
524:
514:
509:
499:
491:
488:
468:Main article:
465:
462:
458:conjugate base
405:
404:
397:
396:
395:
387:
384:
353:
328:
325:
324:
319:
315:standard state
312:
309:
308:
303:
301:Conjugate acid
297:
296:
293:
287:
286:
280:
274:
269:
266:
265:
261:
260:
258:
257:
254:
246:
245:
244:
241:
240:
238:
237:
233:
230:
229:
227:
223:
220:
219:
211:
210:
209:
206:
205:
203:
202:
189:
187:
175:
172:
171:
169:
168:
160:
158:
150:
147:
146:
144:
143:
135:
133:
127:
126:
124:
123:
115:
113:
106:
103:
102:
100:
99:
91:
89:
84:
81:
80:
76:
75:
72:
66:
65:
61:
60:
57:
56:
47:
26:
9:
6:
4:
3:
2:
689:
678:
675:
673:
670:
668:
665:
664:
662:
648:
642:
638:
631:
622:
617:
613:
609:
605:
598:
591:
585:
581:
580:
575:
568:
552:
548:
542:
538:
518:
515:
503:
500:
497:
494:
493:
483:
479:
477:
471:
461:
459:
455:
451:
447:
445:
441:
437:
433:
432:Hückel's rule
429:
425:
421:
417:
407:
401:
393:
383:
381:
377:
373:
369:
365:
361:
347:
343:
339:
335:
322:
316:
310:
307:
304:
302:
299:
298:
294:
292:
289:
288:
275:
272:
268:
267:
262:
253:
252:
249:
242:
228:
218:
217:
214:
207:
199:
195:
191:
190:
188:
178:
174:
173:
166:
162:
161:
159:
153:
149:
148:
141:
137:
136:
134:
132:
129:
128:
121:
117:
116:
114:
110:
105:
104:
97:
93:
92:
90:
87:
83:
82:
77:
71:
67:
62:
52:
48:
43:
39:
38:
34:
19:
636:
630:
611:
608:AIP Advances
607:
597:
578:
574:March, Jerry
567:
555:. Retrieved
550:
541:
473:
448:
427:
423:
413:
359:
341:
337:
331:
285:or Cp
79:Identifiers
444:delocalized
436:double bond
264:Properties
661:Categories
533:References
420:pentagonal
418:, regular-
390:See also:
291:Molar mass
131:ChemSpider
107:3D model (
96:12127-83-2
86:CAS Number
70:IUPAC name
440:lone pair
334:chemistry
576:(2007),
557:14 April
490:See also
346:aromatic
639:. VCH.
165:3490527
152:PubChem
140:2731064
667:Anions
643:
586:
464:Ligand
454:acidic
416:cyclic
370:which
368:ligand
344:is an
336:, the
255:1cccc1
248:SMILES
64:Names
376:metal
374:to a
372:binds
213:InChI
109:JSmol
641:ISBN
584:ISBN
559:2016
438:and
616:doi
378:in
340:or
332:In
182:EPA
155:CID
663::
610:.
606:.
549:.
519:,
504:,
498:,
478:.
382:.
360:Cp
649:.
624:.
618::
612:5
561:.
428:n
424:n
184:)
180:(
111:)
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
