tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.[1]
tert-Butyl isocyanide is isomeric with pivalonitrile, also known as tert-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.
By virtue of the lone electron pair on carbon, isocyanides serves as ligands in coordination chemistry, especially with metals in the 0, +1, and +2 oxidation states. tert-Butyl isocyanide has been shown to stabilize metals in unusual oxidation states, such as Pd(I).[3]
tert-Butyl isocyanide can form hepta-coordinate homoleptic complexes, despite having a large t-Bu group, which is held far away from the metal center because of the linearity of the M-C≡N-C linkages.[4]
tert-Butyl isocycanide forms complexes that are stoichiometrically analogous to certain binary metal carbonyl complexes, such as Fe2(CO)9 and Fe2(tBuNC)9.[5]
Safetyedit
Tert-butyl isocyanide is toxic. Its behavior is similar to that of its close electronic relative carbon monoxide.
Referencesedit
^Malatesta, L. Isocyanide Complexes of MetalsProgress in Inorganic Chemistry, 1959, volume 1, 284-291.
^Carnahan, E.M.; Protasiewicz, J.D.; Lippard, S.J. 15 years of reductive coupling: what have we learned? Acc. Chem. Res. 1993, 26, 90-97
^Bassett, J.M.; Barker, G.K.; Green, M.; Howard, J.A.; Stone, G.A.; Wolsey, W.C. "Chemistry of low-valent metal isocyanide complexes" J.C.S. Dalton, 1981, 219-227.
December 20, 2023
tert, butyl, isocyanide, organic, compound, with, formula, me3cnc, methyl, isocyanide, commonly, called, isonitrile, carbylamine, defined, functional, group, like, most, alkyl, isocyanides, reactive, colorless, liquid, with, extremely, unpleasant, odor, forms,. tert Butyl isocyanide is an organic compound with the formula Me3CNC Me methyl CH3 It is an isocyanide commonly called isonitrile or carbylamine as defined by the functional group C N R tert Butyl isocyanide like most alkyl isocyanides is a reactive colorless liquid with an extremely unpleasant odor It forms stable complexes with transition metals and can insert into metal carbon bonds 1 tert Butyl isocyanide NamesPreferred IUPAC name 2 Isocyano 2 methylpropaneOther names t BuNCIdentifiersCAS Number 7188 38 7 Y3D model JSmol Interactive imageChemSpider 22045 YECHA InfoCard 100 027 776PubChem CID 23577UNII 22S4Z857K3 YCompTox Dashboard EPA DTXSID60222145InChI InChI 1S C5H9N c1 5 2 3 6 4 h1 3H3 YKey FAGLEPBREOXSAC UHFFFAOYSA N YInChI 1 C5H9N c1 5 2 3 6 4 h1 3H3Key FAGLEPBREOXSAC UHFFFAOYALSMILES CC C C N C PropertiesChemical formula C5H9NMolar mass 83 13 g molAppearance Colorless liquidDensity 0 735 g cm3 liquidBoiling point 91 C 196 F 364 K Solubility in water N AExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references tert Butyl isocyanide is prepared by a Hofmann carbylamine reaction In this conversion a dichloromethane solution of tert butylamine is treated with chloroform and aqueous sodium hydroxide in the presence of catalytic amount of the phase transfer catalyst benzyltriethylammonium chloride 2 Me3CNH2 CHCl3 3 NaOH Me3CNC 3 NaCl 3 H2Otert Butyl isocyanide is isomeric with pivalonitrile also known as tert 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 Coordination chemistry editMain article Transition metal isocyanide complexes By virtue of the lone electron pair on carbon isocyanides serves as ligands in coordination chemistry especially with metals in the 0 1 and 2 oxidation states tert Butyl isocyanide has been shown to stabilize metals in unusual oxidation states such as Pd I 3 Pd dba 2 PdCl2 C6H5CN 2 4 t BuNC t BuNC 2PdCl 2 2 dba 2 C6H5CNtert Butyl isocyanide can form hepta coordinate homoleptic complexes despite having a large t Bu group which is held far away from the metal center because of the linearity of the M C N C linkages 4 tert Butyl isocycanide forms complexes that are stoichiometrically analogous to certain binary metal carbonyl complexes such as Fe2 CO 9 and Fe2 tBuNC 9 5 Safety editTert butyl isocyanide is toxic Its behavior is similar to that of its close electronic relative carbon monoxide References edit Malatesta L Isocyanide Complexes of MetalsProgress in Inorganic Chemistry 1959 volume 1 284 291 Gokel G W Widera R P Weber W P 1988 Phase transfer Hofmann carbylamine reaction tert butyl isocyanide Organic Syntheses 55 232 doi 10 15227 orgsyn 055 0096 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Rettig M F Maitlis P M Cotton F A Webb T R Tetrakis tert butyl isocyanide Di m chloro dipalladium I Inorganic Syntheses 1990 28 110 113 ISBN 0 470 13259 0 doi 10 1002 9780470132593 ch29 Carnahan E M Protasiewicz J D Lippard S J 15 years of reductive coupling what have we learned Acc Chem Res 1993 26 90 97 Bassett J M Barker G K Green M Howard J A Stone G A Wolsey W C Chemistry of low valent metal isocyanide complexes J C S Dalton 1981 219 227 Retrieved from https en wikipedia org w index php title Tert Butyl isocyanide amp oldid 1106608566, wikipedia, wiki, book, books, library,
