Literature DB >> 20481599

Enhanced reactivity of RC[triple bond]CZ- (R = H and Cl; Z = O, S, and Se) and the influence of leaving group on the alpha-effect in the E2 reactions.

Xi-Guang Wei1, Xiao-Ming Sun, Xiao-Peng Wu, Yi Ren, Ning-Bew Wong, Wai-Kee Li.   

Abstract

The enhanced reactivity exhibited by six pseudo-alpha-bases, RC[triple bond]CZ(-) (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-pair electrons. The influence of the halide leaving groups on the alpha-effect and the origin of the alpha-effect in the E2 reactions of ethyl halides are investigated and discussed.

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Year:  2010        PMID： 20481599     DOI： 10.1021/jo1006575

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Gas-phase alkyl and N-alkylamino cation affinities of anionic alpha-oxygen nucleophiles (H n XO-; X = N, P, As, O, S, Se, F, Cl, Br; n = 0-2): a theoretical G2(+)M study.

Authors:  Song Geng; Yun-Yun Liu; Ying Xue
Journal:  J Mol Model       Date:  2017-12-05       Impact factor: 1.810

2.  Microsolvation effects on the reactivity of oxy-nucleophiles: the case of gas-phase SN2 reactions of YO-(CH3OH) n=1,2 towards CH3Cl.

Authors:  Liu Yun-Yun; Qiu Fang-Zhou; Zhu Jun; Ren Yi; Lau Kai-Chung
Journal:  J Mol Model       Date:  2017-05-20       Impact factor: 1.810

Review 3.  Nucleophilic Substitution (SN 2): Dependence on Nucleophile, Leaving Group, Central Atom, Substituents, and Solvent.

Authors:  Trevor A Hamlin; Marcel Swart; F Matthias Bickelhaupt
Journal:  Chemphyschem       Date:  2018-04-19       Impact factor: 3.102
  3 in total

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