NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in SN2 reactions

Yuuichi Orimoto; Kazunari Naka; Yuriko Aoki

doi:10.1002/qua.20614

NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in S_N2 reactions

Yuuichi Orimoto, Kazunari Naka, Yuriko Aoki

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14 Citations (Scopus)

Abstract

NBO-based CI/MP through-space/bond interaction analysis was developed to analyze specific orbital interactions under consideration of the effects of electron correlation. This treatment was applied to the analysis of stereoelectronic effects in S_N2 reactions of allyl bromide in which the effects of electron correlation play an important role (ammonia was used as the nucleophilic reagent). The S_N2 activation energy in allyl bromide is lower than that in propyl bromide, because both the σ-π* and π-σ* interactions in allyl bromide contribute equally to the stabilization of the transition state.

Original language	English
Pages (from-to)	911-918
Number of pages	8
Journal	International Journal of Quantum Chemistry
Volume	104
Issue number	6
DOIs	https://doi.org/10.1002/qua.20614
Publication status	Published - Sept 20 2005

All Science Journal Classification (ASJC) codes

Atomic and Molecular Physics, and Optics
Condensed Matter Physics
Physical and Theoretical Chemistry

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NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in S_N2 reactions

Abstract

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