原创力文档symmetry analysis in mechanistic studies of nucleophilic substitution and β-elimination reactions对称性分析在机械的亲核取代和β-elimination反应的研究.pdfVIP
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symmetry analysis in mechanistic studies of nucleophilic substitution and β-elimination reactions对称性分析在机械的亲核取代和β-elimination反应的研究
Symmetry 2010, 2, 201-212; doi:10.3390/sym2010201
OPEN ACCESS
symmetry
ISSN 2073-8994
/journal/symmetry
Article
Symmetry Analysis in Mechanistic Studies of Nucleophilic
Substitution and β-Elimination Reactions
Xiaoping Sun
Department of Natural Science and Mathematics, University of Charleston, 2300 MacCorkle Avenue,
S. E., Charleston, WV 25304, USA; E-Mail: xiaopingsun@
Received: 31 January 2010 / Accepted: 20 February 2010 / Published: 25 February 2010
Abstract: A mechanistic study of the bimolecular nucleophilic substitution (SN2) reaction
for halomethane CH X (X = Cl, Br, or I) is approached by using symmetry principles and
3
3
molecular orbital theory. The electrophilicity of the functionalized sp –carbon is
attributable to a 2p-orbital-based antibonding MO along the C–X bond. This antibonding
MO, upon accepting an electron pair from a nucleophile, gives rise to dissociation of the
C–X bond and formation of a new Nuc–C bond. Correlations are made between the
- -
molecular orbitals of reactants (Nuc and CH X) and products (NucCH and X ). Similar
3 3
symmetry analysis has been applied to mechanistic study of the b
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