use of linear free energy relationships (lfers) to elucidate the mechanisms of reaction of a γ-methyl-β-alkynyl and an ortho-substituted aryl chloroformate ester使用线性自由能关系(lfers)反应机制的阐明γ-methyl-β-alkynyl和ortho-substituted芳基氯甲酸酯酯.pdfVIP

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use of linear free energy relationships (lfers) to elucidate the mechanisms of reaction of a γ-methyl-β-alkynyl and an ortho-substituted aryl chloroformate ester使用线性自由能关系(lfers)反应机制的阐明γ-methyl-β-alkynyl和ortho-substituted芳基氯甲酸酯酯.pdf

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use of linear free energy relationships (lfers) to elucidate the mechanisms of reaction of a γ-methyl-β-alkynyl and an ortho-substituted aryl chloroformate ester使用线性自由能关系(lfers)反应机制的阐明γ-methyl-β-alkynyl和ortho-substituted芳基氯甲酸酯酯

Int. J. Mol. Sci. 2012, 13, 665-682; doi:10.3390/ijm OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 /journal/ijms Article Use of Linear Free Energy Relationships (LFERs) to Elucidate the Mechanisms of Reaction of a γ-Methyl-β-alkynyl and an ortho-Substituted Aryl Chloroformate Ester Malcolm J. D’Souza 1,*, Jaci A. Knapp 1, Gabriel A. Fernandez-Bueno 1 and Dennis N. Kevill 2,* 1 Department of Chemistry, Wesley College, 120 N. State Street, Dover, DE 19901, USA; E-Mails: jaci.knapp@ (J.A.K.); gabriel.fernandez@ (G.A.F.-B.) 2 Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA * Authors to whom correspondence should be addressed; E-Mails: dsouzama@ (M.J.D.); dkevill@ (D.N.K.); Tel.: +1-302-736-2528 (M.J.D.); +1-815-753-6882 (D.N.K.); Fax: +1-302-736-2301 (M.J.D.); +1-815-753-4802 (D.N.K.). Received: 20 December 2011; in revised form: 5 January 2012 / Accepted: 5 January 2012 / Published: 10 January 2012 Abstract: The specific rates of solvolysis of 2-butyn-1-yl-chloroformate (1) and 2-methoxyphenyl chloroformate (2) are studied at 25.0 °C in a series of binary aqueous- organic mixtures. The rates of reaction obtained are then analyzed using the extended Grunwald-Winstein (G-W) equation and the results are compared to previously published G-W analyses for phenyl chloroformate (3), propargyl chloroformate (4), p -methoxyphenyl choroformate (5), and p -ni