Theoretical gas-phase stabilities of α-trimethylsilyl-substituted tertiary carbenium ions

被引：5
|
作者：
Grunenberg, J
Laschat, S
Dickner, T
机构：
[1] Tech Univ Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 24期
关键词：
silanes; carbenoids; density functional calculations; gas-phase calculations; compliance constants;
D O I：
10.1002/ejoc.200300273
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Theoretical hydride ion affinities in the gas phase are presented for alpha-SiMe3-substituted tertiary carbenium ions. Thermodynamic stabilization of the "nascent" ions by a single trimethylsilyl group is weaker than by a tert-butyl group but comparable to the effect of a methyl group. In the case of the cyclopropenylium cation, the stabilization by a trimethylsilyl group even exceeds the effectiveness of a tertbutyl group. Compliance constants are used to quantify the chemical concept of hyperconjugation. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
引用
收藏
页码：4897 / 4901
页数：5
相关论文
共 50 条
  • [41] Gas-phase reactions of nitronium ions with acetylene and ethylene: An experimental and theoretical study
    Bernardi, F
    Cacace, F
    de Petris, G
    Pepi, F
    Rossi, I
    Troiani, A
    CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (03) : 537 - 544
  • [42] THEORETICAL-STUDY OF THE THERMOCHEMICAL STABILITIES OF THE ISOMERS OF [H2,SI,O].+ IN THE GAS-PHASE
    HRUSAK, J
    BOHME, DK
    WLODEK, S
    SCHWARZ, H
    JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (13): : 5355 - 5358
  • [43] GAS-PHASE ALKYLATION OF PHENYLTRIMETHYLSILANES - USING THE TRIMETHYLSILYL GROUP TO PROBE PROTON SHIFTS IN GASEOUS ARENIUM IONS
    ATTINA, M
    CACACE, F
    RICCI, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 5937 - 5942
  • [44] GAS-PHASE REACTIONS OF IONS AND THEIR SOLVATES
    DEPUY, CH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 16 - PHYS
  • [45] INVESTIGATIONS OF HALONIUM IONS IN THE GAS-PHASE
    HOLLIS, J
    TEDDER, JM
    WALKER, GS
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (08): : 1187 - 1194
  • [46] STRUCTURE AND REACTIVITY OF GAS-PHASE IONS
    JENNINGS, KR
    CHEMISTRY IN BRITAIN, 1986, 22 (07) : 658 - 659
  • [47] Gas-phase fragmentation of oligonucleotide ions
    Wu, J
    McLuckey, SA
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2004, 237 (2-3) : 197 - 241
  • [48] FORMATION OF THIOACYLIUM IONS IN THE GAS-PHASE
    RAHMAN, NA
    FISHER, CL
    CASERIO, MC
    ORGANIC MASS SPECTROMETRY, 1988, 23 (07): : 517 - 520
  • [49] GAS-PHASE CLUSTER IONS - PREFACE
    BOWERS, MT
    JARROLD, MF
    STACE, AJ
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, 1990, 102 : R9 - R9
  • [50] GAS-PHASE SYNTHESIS OF METALLOPORPHYRIN IONS
    IRIKURA, KK
    BEAUCHAMP, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) : 2767 - 2768
12345