analysis of the nucleophilic solvation effects in isopropyl chlorothioformate solvolysis分析异丙酯的亲核溶解效果chlorothioformate溶剂分解.pdfVIP

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analysis of the nucleophilic solvation effects in isopropyl chlorothioformate solvolysis分析异丙酯的亲核溶解效果chlorothioformate溶剂分解.pdf

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analysis of the nucleophilic solvation effects in isopropyl chlorothioformate solvolysis分析异丙酯的亲核溶解效果chlorothioformate溶剂分解

Int. J. Mol. Sci. 2010, 11, 2597-2611; doi:10.3390/ijm OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 /journal/ijms Article Analysis of the Nucleophilic Solvation Effects in Isopropyl Chlorothioformate Solvolysis Malcolm J. D’Souza 1,*, Brian P. Mahon 1 and Dennis N. Kevill 2,* 1 Department of Chemistry, Wesley College, 120 N. State Street, Dover, DE 19901-3875, USA 2 Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115-2862, USA * Author to whom correspondence should be addressed; E-Mails: dsouzama@ (M.J.D.); dkevill@ (D.N.K.). Received: 9 June 2010; in revised form: 21 June 2010 / Accepted: 28 June 2010 / Published: 29 June 2010 Abstract: Correlation of the solvent effects through application of the extended Grunwald- Winstein equation to the solvolysis of isopropyl chlorothioformate results in a sensitivity value of 0.38 towards changes in solvent nucleophilicity (l) and a sensitivity value of 0.72 towards changes in solvent ionizing power (m). This tangible l value coupled with the negative entropies of activation observed indicates a favorable predisposition towards a modest rear-side nucleophilic solvation of a developing carbocation. Only in 100% ethanol was the bimolecular pathway dominant. These observations are very different from those obtained for the solvolysis of isopropyl chloroformate, where dual reaction channels were