216:
161:
24:
369:
849:
Noviandri, Indra; Brown, Kylie N.; Fleming, Douglas S.; Gulyas, Peter T.; Lay, Peter A.; Masters, Anthony F.; Phillips, Leonidas (1 August 1999). "The
Decamethylferrocenium/Decamethylferrocene Redox Couple: A Superior Redox Standard to the Ferrocenium/Ferrocene Redox Couple for Studying Solvent
941:
Freyberg, Derek P.; Robbins, John L.; Raymond, Kenneth N.; Smart, James C. (1979). "Crystal and molecular structures of decamethylmanganocene and decamethylferrocene. Static Jahn-Teller distortion in a metallocene".
890:
Malischewski, M.; Adelhardt, M.; Sutter, J.; Meyer, K.; Seppelt, K. (2016). "Isolation and structural and electronic characterization of salts of the decamethylferrocene dication".
755:
King, R. B.; Bisnette, M. B. (1967). "Organometallic
Chemistry of the Transition Metals XXI. Some π-pentamethylcyclopentadienyl Derivatives of Various Transition Metals".
118:
822:
Torriero, Angel A. J. (2014). "Characterization of decamethylferrocene and ferrocene in ionic liquids: argon and vacuum effect on their electrochemical properties".
608:
Like ferrocene, decamethylferrocene forms a stable cation because Fe(II) is easily oxidized to Fe(III). Because of the electron donating methyl groups on the
382:
1024:
265:
377:
1029:
596:
rings. The average distance between iron and each carbon is approximately 2.050 Å. This structure has been confirmed by
230:
389:
582:
345:
156:
460:
194:
546:
211:
971:
1034:
597:
138:
525:
This compound is a yellow crystalline solid that is used in chemical laboratories as a weak
899:
94:
36:
786:
Connelly, N.; Geiger, W. E. (1996). "Chemical Redox Agents for
Organometallic Chemistry".
549:. This method can be used to produce other decamethylcyclopentadienyl sandwich compounds.
8:
1019:
757:
215:
160:
84:
903:
923:
769:
996:
944:
915:
867:
804:
698:) decamethylferrocene is oxidized to a stable dication with an iron(IV) core. In the
648:
456:
444:
409:
927:
835:
182:
988:
952:
907:
859:
831:
796:
765:
288:
612:
groups, decamethylferrocene is more reducing than is ferrocene. In a solution of
500:
976:"Oxygen and proton reduction by decamethylferrocene in non-aqueous acidic media"
360:
1013:
980:
871:
334:
149:
911:
1000:
975:
919:
808:
613:
492:
956:
863:
788:
313:
129:
800:
23:
992:
545:
Decamethylferrocene is prepared in the same manner as ferrocene from
530:
526:
488:
359:
Except where otherwise noted, data are given for materials in their
496:
117:
718:
rings are parallel. In contrast, a tilt angle of 17° between the
239:
InChI=1S/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2
169:
889:
249:
InChI=1/2C10H15.Fe/c2*1-6-7(2)9(4)10(5)8(6)3;/h2*1-5H3;/q2*-1;+2
107:
974:; Samec, Zdenek; Ersoz, Mustafa; Girault, Hubert H. (2010).
199:
940:
848:
448:
339:
291 to 295 °C (556 to 563 °F; 564 to 568 K)
503:
rings. The name and formula are often abbreviated to
850:
970:Su, Bin; Hatay, Imren; Ge, Pei Yu; Mendez, Manuel;
722:rings is observed in the crystal structure of the
1011:
181:
969:
93:
785:
533:to iron(III), yielding the monovalent cation
63:1,1′,2,2′,3,3′,4,4′,5,5′-Decamethyl-ferrocene
754:
487:). It can also be viewed as a derivative of
651:by decamethylferrocene in acidic solution.
214:
159:
137:
821:
406:bis(pentamethylcyclopentadienyl)iron(II)
66:Bis(pentamethylcyclopentadienyl)iron(II)
885:
883:
881:
537:, and even to higher oxidation states.
210:
1012:
750:
748:
746:
150:
1025:Pentamethylcyclopentadienyl complexes
781:
779:
242:Key: SEYZDJPFVVXSRB-UHFFFAOYSA-N
57:-pentamethylcyclopentadienyl)iron(II)
878:
815:
273:C1c(c(c(c1C)C)C)C.C1c(c(c(c1C)C)C)C.
934:
852:The Journal of Physical Chemistry B
842:
743:
252:Key: SEYZDJPFVVXSRB-UHFFFAOYAP
172:
13:
776:
603:
14:
1046:
624:couple is −0.59 V compared to a
616:the reduction potential for the
367:
300:
22:
836:10.1016/j.electacta.2014.06.005
581:The product can be purified by
363:(at 25 °C , 100 kPa).
963:
654:Using powerful oxidants (e.g.
632:reference (−0.48 V vs Fc/
540:
529:. The iron(II) core is easily
294:
1:
770:10.1016/S0022-328X(00)91042-8
737:
1030:One-electron reducing agents
306:
7:
461:pentamethylcyclopentadienyl
10:
1051:
547:pentamethylcyclopentadiene
357:
329:Yellow crystalline solid
281:
261:
226:
77:
47:
35:
30:
21:
647:). Oxygen is reduced to
447:, whose molecule has an
912:10.1126/science.aaf6362
972:Corminboeuf, Clemence
598:X-ray crystallography
535:decamethylferrocenium
60:Decamethyl-ferrocene
37:Preferred IUPAC name
17:Decamethylferrocene
957:10.1021/ja00498a017
904:2016Sci...353..678M
824:Electrochimica Acta
758:J. Organomet. Chem.
402:Decamethylferrocene
321: g·mol
41:Decamethylferrocene
18:
457:coordination bonds
390:Infobox references
69:Permethylferrocene
16:
987:(17): 2918–2919.
945:J. Am. Chem. Soc.
898:(6300): 678–682.
864:10.1021/jp991381+
858:(32): 6713–6722.
801:10.1021/cr940053x
649:hydrogen peroxide
445:sandwich compound
410:chemical compound
398:Chemical compound
396:
395:
195:CompTox Dashboard
119:Interactive image
1042:
1005:
1004:
993:10.1039/B926963K
967:
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501:cyclopentadienyl
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485:
484:
481:
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454:
442:
430:
380:
374:
371:
370:
320:
308:
302:
296:
289:Chemical formula
219:
218:
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201:
185:
174:
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121:
97:
26:
19:
15:
1050:
1049:
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604:Redox reactions
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495:replacing each
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385: ?)
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12:
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5:
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1038:
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1027:
1022:
1007:
1006:
962:
951:(4): 892–897.
933:
877:
841:
814:
795:(2): 877–910.
775:
764:(2): 287–297.
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739:
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592:has staggered
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361:standard state
358:
355:
354:
353:413 K, 5.3 Pa
351:
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212:DTXSID80923743
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2:
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981:Chem. Commun.
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599:
584:
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548:
538:
536:
532:
528:
523:
506:
502:
498:
494:
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462:
458:
450:
446:
412:with formula
411:
407:
403:
391:
384:
379:
362:
356:
352:
349:
343:
342:
338:
336:
335:Melting point
333:
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328:
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317:
315:
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196:
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155:
153:
151:ECHA InfoCard
148:
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109:
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59:
56:
52:
51:
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38:
34:
29:
25:
20:
1035:Metallocenes
984:
979:
965:
948:
943:
936:
895:
891:
855:
851:
844:
827:
823:
817:
792:
787:
761:
756:
653:
614:acetonitrile
607:
580:
544:
534:
524:
504:
499:atom of its
493:methyl group
459:between two
455:attached by
405:
401:
400:
78:Identifiers
54:
48:Other names
830:: 235–244.
583:sublimation
541:Preparation
443:. It is a
346:Sublimation
326:Appearance
282:Properties
157:100.116.086
1020:Ferrocenes
1014:Categories
789:Chem. Rev.
738:References
714:salt, the
618:[FeCp*
348:conditions
314:Molar mass
130:ChemSpider
106:3D model (
95:12126-50-0
85:CAS Number
872:1520-6106
626:[FeCp
527:reductant
491:, with a
489:ferrocene
1001:20386822
928:43385610
920:27516596
809:11848774
577:+ 2 LiCl
561:) + FeCl
531:oxidized
497:hydrogen
463:anions (
449:iron(II)
900:Bibcode
892:Science
451:cation
383:what is
381: (
319:326.305
183:5148079
170:PubChem
139:4321548
999:
926:
918:
870:
807:
734:salt.
693:HF/SbF
677:XeF/Sb
565:→ Fe(C
553:2 Li(C
378:verify
375:
266:SMILES
31:Names
924:S2CID
675:, or
587:FeCp*
517:FeCp*
408:is a
231:InChI
108:JSmol
997:PMID
916:PMID
868:ISSN
805:PMID
505:DmFc
414:Fe(C
53:Bis(
989:doi
953:doi
949:101
908:doi
896:353
860:doi
856:103
832:doi
828:137
797:doi
766:doi
724:SbF
720:Cp*
716:Cp*
691:in
668:in
663:AsF
661:or
656:SbF
636:in
610:Cp*
594:Cp*
515:or
469:(CH
465:Cp*
431:or
418:(CH
404:or
200:EPA
173:CID
1016::
995:.
985:46
978:.
922:.
914:.
906:.
894:.
880:^
866:.
854:.
826:.
803:.
793:96
778:^
745:^
710:11
700:Sb
687:11
670:SO
642:Cl
638:CH
634:Fc
600:.
585:.
569:Me
557:Me
522:.
513:Fc
511:10
509:Me
507:,
467:,
453:Fe
441:Fe
439:30
435:20
307:Fe
304:30
298:20
1003:.
991::
959:.
955::
930:.
910::
902::
874:.
862::
838:.
834::
811:.
799::
772:.
768::
762:8
730:6
727:−
707:−
704:F
702:2
695:5
684:−
681:F
679:2
672:2
665:5
658:5
644:2
640:2
630:]
628:2
622:]
620:2
589:2
575:2
573:)
571:5
567:5
563:2
559:5
555:5
519:2
483:5
480:−
477:C
475:5
473:)
471:3
437:H
433:C
428:2
426:)
424:5
422:)
420:3
416:5
373:N
301:H
295:C
202:)
198:(
110:)
55:η
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