Basicity of a stable carbene, 1,3-di-tert-butylimidazol-2-ylidene, in THF

被引：216

作者：

Kim, YJ ^{[1
]}

Streitwieser, A ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 20期

关键词：

D O I：

10.1021/ja025628j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The basicity of 1,3-di-tert-butylimidazol-2-ylidene (1) was measured in THF against three hydrocarbon indicators. Both ion pairs and free ions were found and the corresponding equilibrium constants were measured. Homoconjugation was not found in either THF or DMSO. The carbene is effectively more basic in DMSO by several pK units, probably because of hydrogen bonding of 1-H+ to DMSO. Model ab initio computations are consistent with these results.

引用

页码：5757 / 5761

页数：5

共 37 条

[31] SREITWIESER A, 2001, ORG LETT, V3, P2599
[32] ACIDITIES OF WEAK ACIDS IN DIMETHYL SULFOXIDE .2. HAMMETT ACIDITY FUNCTION
STEINER, EC
GILBERT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (02) : 382 - &
[33] CARBON ACIDITY .78. EXTENDED CESIUM ION-PAIR INDICATOR SCALE IN TETRAHYDROFURAN
STREITWIESER, A
CIULA, JC
KROM, JA
THIELE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1074 - 1076
[34] Extended lithium ion pair indicator scale in tetrahydrofuran
Streitwieser, A
Wang, DZ
Stratakis, M
Facchetti, A
Gareyev, R
Abbotto, A
Krom, JA
Kilway, KV
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (06) : 765 - 769
[35] Ion pair basicity of some amines in THF: Implications for ion pair acidity scales
Streitwieser, A
Kim, YJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 11783 - 11786
[36] *WAV INC, 1996, PC SPART PRO
[37] N-heterocyclic carbenes:: novel ruthenium-alkylidene complexes
Weskamp, T
Kohl, FJ
Herrmann, WA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 582 (02) : 362 - 365

← 1 2 3 4 →