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

Research output: Contribution to journal › Article › peer-review

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 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 - Sep 20 2005

All Science Journal Classification (ASJC) codes

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

Access to Document

10.1002/qua.20614

Fingerprint Dive into the research topics of 'NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in S<sub>N</sub>2 reactions'. Together they form a unique fingerprint.

Cite this

@article{5a8a5760ea294266849eaba614b692fe,

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

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.",

author = "Yuuichi Orimoto and Kazunari Naka and Yuriko Aoki",

year = "2005",

month = sep,

day = "20",

doi = "10.1002/qua.20614",

language = "English",

volume = "104",

pages = "911--918",

journal = "International Journal of Quantum Chemistry",

issn = "0020-7608",

publisher = "John Wiley and Sons Inc.",

number = "6",

}

TY - JOUR

T1 - NBO-based CI/MP through-space/bond interaction analysis and its application to stereoelectronic effects in SN2 reactions

AU - Orimoto, Yuuichi

AU - Naka, Kazunari

AU - Aoki, Yuriko

PY - 2005/9/20

Y1 - 2005/9/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=26944480436&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=26944480436&partnerID=8YFLogxK

U2 - 10.1002/qua.20614

DO - 10.1002/qua.20614

M3 - Article

AN - SCOPUS:26944480436

VL - 104

SP - 911

EP - 918

JO - International Journal of Quantum Chemistry

JF - International Journal of Quantum Chemistry

SN - 0020-7608

IS - 6