NBO‐based CI/MP through‐space/bond interaction analysis and its application to stereoelectronic effects in S N 2 reactions | Zendy

Orimoto Yuuichi | Zendy; Naka Kazunari | Zendy; Aoki Yuriko | Zendy

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NBO‐based CI/MP through‐space/bond interaction analysis and its application to stereoelectronic effects in S N 2 reactions

Author(s) -

Orimoto Yuuichi,

Naka Kazunari,

Aoki Yuriko

Publication year - 2005

Publication title -

international journal of quantum chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.484

H-Index - 105

eISSN - 1097-461X

pISSN - 0020-7608

DOI - 10.1002/qua.20614

Subject(s) - natural bond orbital , chemistry , bromide , allyl bromide , nucleophile , reagent , computational chemistry , electronic correlation , medicinal chemistry , organic chemistry , density functional theory , molecule , catalysis

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 N 2 reactions of allyl bromide in which the effects of electron correlation play an important role (ammonia was used as the nucleophilic reagent). The S N 2 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. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2005

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