Synthesis and reactivity of subvalent compounds Part 10. Fast deuterium labeling and the basicity of stable diamino carbenes (imidazole-2-ylidenes)

被引:34
作者
Denk, MK [1 ]
Rodezno, JM [1 ]
机构
[1] Univ Toronto, Dept Chem, Mississauga, ON L5L 1C6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
carbenes; imidazol-2-ylidenes; hydrogen-deuterium exchange; proton affinities; DFT calculations; mechanism;
D O I
10.1016/S0022-328X(00)00765-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The aromatic ring protons in imidazol-2-ylidenes (Arduengo carbenes) undergo rapid deuterium-hydrogen exchange in DMSO-d(6), CD3OD and D2O. (C) 2001 Published by Elsevier Science B.V.
引用
收藏
页码:737 / 740
页数:4
相关论文
共 37 条
[1]   Complexation of stable carbenes with alkali metals [J].
Alder, RW ;
Blake, ME ;
Bortolotti, C ;
Bufali, S ;
Butts, CP ;
Linehan, E ;
Oliva, JM ;
Orpen, AG ;
Quayle, MJ .
CHEMICAL COMMUNICATIONS, 1999, (03) :241-242
[2]   Diaminocarbenes;: Calculation of barriers to rotation about Ccarbene-N bonds, barriers to dimerization, proton affinities, and 13C NMR shifts [J].
Alder, RW ;
Blake, ME ;
Oliva, JM .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (50) :11200-11211
[3]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[4]   A STABLE DIAMINOCARBENE [J].
ARDUENGO, AJ ;
GOERLICH, JR ;
MARSHALL, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11027-11028
[5]   PHOTOELECTRON-SPECTROSCOPY OF A CARBENE/SILYLENE/GERMYLENE SERIES [J].
ARDUENGO, AJ ;
BOCK, H ;
CHEN, H ;
DENK, M ;
DIXON, DA ;
GREEN, JC ;
HERRMANN, WA ;
JONES, NL ;
WAGNER, M ;
WEST, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6641-6649
[6]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[7]   An air stable carbene and mixed carbene "dimers" [J].
Arduengo, AJ ;
Davidson, F ;
Dias, HVR ;
Goerlich, JR ;
Khasnis, D ;
Marshall, WJ ;
Prakasha, TK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12742-12749
[8]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[9]   Stable versions of transient push-pull carbenes: Extending lifetimes from nanoseconds to weeks [J].
Buron, C ;
Gornitzka, H ;
Romanenko, V ;
Bertrand, G .
SCIENCE, 2000, 288 (5467) :834-836
[10]   The prediction of vibrational frequencies of inorganic molecules using density functional theory [J].
Bytheway, I ;
Wong, MW .
CHEMICAL PHYSICS LETTERS, 1998, 282 (3-4) :219-226