236:
161:
40:
31:
388:
850:"Chemistry of low-valent metal isocyanide complexes. Part 3. The synthesis, structure, and dynamic behaviour of nonakis(ethyl and isopropyl isocyanide)di-iron and -ruthenium complexes. Crystal structure of [Fe 2 (µ-CNEt) 3 (CNEt) 6 ]"
542:-butyl cyanide. The difference, as with all carbylamine analogs of nitriles, is that the bond joining the CN functional group to the parent molecule is made on the nitrogen, not the carbon.
401:
756:
285:
793:
713:
551:
250:
454:-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable
903:
848:
Bassett, Jean-Marie; Barker, Geoffrey K.; Green, Michael; Howard, Judith A. K.; Stone, F. Gordon A.; Wolsey, Wayne C. (1981).
898:
408:
193:
118:
214:
729:
Gokel, G.W.; Widera, R.P.; Weber, W.P. (1988). "Phase-transfer
Hofmann carbylamine reaction: tert-butyl isocyanide".
496:
156:
565:
750:
39:
888:
771:
455:
58:
231:
576:-Butyl isocyanide has been shown to stabilize metals in unusual oxidation states, such as Pd(I).
84:
775:
641:-Butyl isocycanide forms complexes that are stoichiometrically analogous to certain binary metal
693:
865:
830:
789:
709:
672:-Butyl isocyanide is toxic. Its behavior is similar to that of its close electronic relative
473:
893:
857:
822:
781:
738:
701:
488:
459:
447:
431:
427:
366:
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138:
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355:
149:
30:
810:
589:
182:
785:
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Carnahan, Edmund M.; Protasiewicz, John D.; Lippard, Stephen J. (1993-03-01).
705:
631:
complexes, despite having a large t-Bu group, which is held far away from the
628:
484:
443:
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129:
869:
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742:
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Rettig, M. F.; Maitlis, P. M.; Cotton, F. A.; Webb, T. R. (January 1990).
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Except where otherwise noted, data are given for materials in their
632:
117:
107:
446:, commonly called isonitrile or carbylamine, as defined by the
219:
38:
29:
811:"The 15 years of reductive coupling: what have we learned?"
777:
Tetrakis( tert -Butyl
Isocyanide)Di-μ-Chlorodipalladium(I)
635:
center because of the linearity of the M-C≡N-C linkages.
472:-Butyl isocyanide is prepared by a Hofmann carbylamine
396:
780:. Vol. 28 (1 ed.). Wiley. pp. 110–113.
700:. Vol. 1 (1 ed.). Wiley. pp. 283–379.
476:. In this conversion, a dichloromethane solution of
181:
93:
568:, especially with metals in the 0, +1, and +2
8:
755:: CS1 maint: multiple names: authors list (
627:-Butyl isocyanide can form hepta-coordinate
234:
159:
137:
15:
201:
684:
556:By virtue of the lone electron pair on
290:
255:
230:
748:
150:
552:Transition metal isocyanide complexes
360:91 °C (196 °F; 364 K)
262:Key: FAGLEPBREOXSAC-UHFFFAOYSA-N
7:
534:-Butyl isocyanide is isomeric with
272:Key: FAGLEPBREOXSAC-UHFFFAOYAL
172:
259:InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3
14:
462:and can insert into metal-carbon
269:InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
694:"Isocyanide Complexes of Metals"
386:
698:Progress in Inorganic Chemistry
382:(at 25 °C , 100 kPa).
696:. In Cotton, F. Albert (ed.).
692:Malatesta, L. (January 1959).
1:
815:Accounts of Chemical Research
854:J. Chem. Soc., Dalton Trans.
25:
920:
786:10.1002/9780470132593.ch29
549:
63:2-Isocyano-2-methylpropane
706:10.1002/9780470166024.ch5
376:
332:83.13 g/mol
301:
281:
246:
77:
69:
57:
52:
24:
743:10.15227/orgsyn.055.0096
560:, isocyanides serves as
904:Foul-smelling chemicals
499:benzyltriethylammonium
497:phase transfer catalyst
566:coordination chemistry
546:Coordination chemistry
523:CNC + 3 NaCl + 3 H
43:
34:
645:complexes, such as Fe
42:
33:
899:Tert-butyl compounds
862:10.1039/DT9810000219
438:CNC (Me = methyl, CH
59:Preferred IUPAC name
827:10.1021/ar00027a003
772:Angelici, Robert J.
491:in the presence of
367:Solubility in water
350:0.735 g/cm, liquid
21:
519:+ 3 NaOH → Me
409:Infobox references
44:
35:
20:-Butyl isocyanide
16:
795:978-0-471-52619-3
731:Organic Syntheses
715:978-0-470-17589-7
460:transition metals
424:-Butyl isocyanide
417:Chemical compound
415:
414:
340:Colorless liquid
215:CompTox Dashboard
119:Interactive image
48:
47:
911:
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689:
612:+ 2 dba + 2 C
538:, also known as
489:sodium hydroxide
483:is treated with
448:functional group
428:organic compound
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393:
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309:Chemical formula
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674:carbon monoxide
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856:(1): 219–227.
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536:pivalonitrile
533:
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442:). It is an
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356:Boiling point
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151:ECHA InfoCard
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821:(3): 90–97.
818:
814:
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751:cite journal
734:
730:
724:
697:
687:
669:
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638:
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608:-BuNC →
605:
573:
555:
539:
531:
530:
487:and aqueous
478:
469:
468:
451:
421:
420:
419:
78:Identifiers
70:Other names
17:
889:Isocyanides
481:-butylamine
337:Appearance
302:Properties
157:100.027.776
883:Categories
680:References
629:homoleptic
485:chloroform
444:isocyanide
328:Molar mass
203:22S4Z857K3
130:ChemSpider
106:3D model (
85:CAS Number
870:0300-9246
835:0001-4842
572:states.
570:oxidation
493:catalytic
456:complexes
430:with the
293:CC(C)(C)#
95:7188-38-7
643:carbonyl
501:chloride
474:reaction
450:C≡N-R.
322:N
894:Ligands
774:(ed.).
737:: 232.
657:(tBuNC)
584:+ PdCl
580:Pd(dba)
562:ligands
515:+ CHCl
432:formula
402:what is
400: (
346:Density
170:PubChem
868:
833:
792:
712:
665:Safety
653:and Fe
558:carbon
426:is an
397:verify
394:
286:SMILES
72:t-BuNC
53:Names
633:metal
604:+ 4
464:bonds
458:with
251:InChI
183:23577
139:22045
108:JSmol
866:ISSN
831:ISSN
790:ISBN
757:link
710:ISBN
670:tert
649:(CO)
639:tert
625:tert
574:tert
540:tert
532:tert
479:tert
470:tert
452:tert
422:tert
372:N/A
194:UNII
18:tert
858:doi
823:doi
782:doi
739:doi
702:doi
564:in
511:CNH
503:.
466:.
220:EPA
173:CID
885::
864:.
852:.
829:.
819:26
817:.
813:.
788:.
753:}}
749:{{
735:55
733:.
708:.
676:.
661:.
620:CN
598:CN
507:Me
434:Me
872:.
860::
837:.
825::
798:.
784::
759:)
745:.
741::
718:.
704::
659:9
655:2
651:9
647:2
618:5
616:H
614:6
610:2
606:t
602:2
600:)
596:5
594:H
592:6
590:C
588:(
586:2
582:2
527:O
525:2
521:3
517:3
513:2
509:3
440:3
436:3
392:Y
320:9
318:H
316:5
314:C
222:)
218:(
110:)
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