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

Yuuichi Orimoto, Kazunari Naka, Yuriko Aoki

    Research output: Contribution to journalArticle

    13 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 SN2 reactions of allyl bromide in which the effects of electron correlation play an important role (ammonia was used as the nucleophilic reagent). The SN2 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 languageEnglish
    Pages (from-to)911-918
    Number of pages8
    JournalInternational Journal of Quantum Chemistry
    Volume104
    Issue number6
    DOIs
    Publication statusPublished - Sep 20 2005

    Fingerprint

    bromides
    Electron correlations
    interactions
    Ammonia
    Stabilization
    Activation energy
    reagents
    ammonia
    electrons
    stabilization
    activation energy
    orbitals
    allyl bromide
    1-bromopropane

    All Science Journal Classification (ASJC) codes

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

    Cite this

    NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in SN2 reactions. / Orimoto, Yuuichi; Naka, Kazunari; Aoki, Yuriko.

    In: International Journal of Quantum Chemistry, Vol. 104, No. 6, 20.09.2005, p. 911-918.

    Research output: Contribution to journalArticle

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