原创力文档use of empirical correlations to determine solvent effects in the solvolysis of s-methyl chlorothioformate使用的经验相关性来确定溶剂影响的溶剂分解s-methyl chlorothioformate.pdfVIP
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use of empirical correlations to determine solvent effects in the solvolysis of s-methyl chlorothioformate使用的经验相关性来确定溶剂影响的溶剂分解s-methyl chlorothioformate
Int. J. Mol. Sci. 2010, 11, 2253-2266; doi:10.3390/ijm
OPEN ACCESS
International Journal of
Molecular Sciences
ISSN 1422-0067
/journal/ijms
Article
Use of Empirical Correlations to Determine Solvent Effects in
the Solvolysis of S-Methyl Chlorothioformate
Malcolm J. D’Souza 1,*, Stefan M. Hailey 1, and Dennis N. Kevill 2,*
1 Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA
2 Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois
60115-2862, USA
* Authors to whom correspondence should be addressed; E-Mails: dsouzama@ (M.J.D.);
dkevill@ (D.N.K.).
Received: 5 May 2010; in revised form: 12 May 2010 / Accepted: 24 May 2010 /
Published: 25 May 2010
Abstract: The specific rates of solvolysis of S-methyl chlorothioformate (MeSCOCl) are
analyzed in 20 solvents of widely varying nucleophilicity and ionizing power at 25.0 °C
using the extended Grunwald-Winstein Equation. A stepwise S 1 (D + A ) mechanism is
N N N
proposed in the more ionizing solvents including six aqueous fluoroalcohols. In these
solvents, a large sensitivity value of 0.79 towards changes in solvent nucleophilicity (l) is
indicative of profound rearside nucleophilic solvation of the developing carbocation. In
twelve of the more nucleophilic pure
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