Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Fluoroformate and a Consideration of Leaving Group Effects

Reactions of n-propyl fluoroformate in a variety of pure and binary solvents have been studied at 40.0 {^{\circ}C}. The extended (two-term) Grunwald-Winstein equation has been applied to the specific rates of solvolysis of npropyl fluoroformate. The sensitivities (l = 1.80 ${\pm}$ 0.17 and m = 0.96...

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Published inBulletin of the Korean Chemical Society Vol. 29; no. 9; pp. 1747 - 1751
Main Authors Seong, Mi-Hye, Kyong, Jin-Burm, Kim, Dong-Kook, Kevill, Dennis N
Format Journal Article
LanguageKorean
Published 대한화학회 01.09.2008
Subjects
화학
Grunwald-Winstein equation
Addition-elimination
n-Propyl fluoroformate
Leaving group effect
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Summary:Reactions of n-propyl fluoroformate in a variety of pure and binary solvents have been studied at 40.0 {^{\circ}C}. The extended (two-term) Grunwald-Winstein equation has been applied to the specific rates of solvolysis of npropyl fluoroformate. The sensitivities (l = 1.80 ${\pm}$ 0.17 and m = 0.96 ${\pm}$ 0.10) to changes in solvent nucleophilicity and solvent ionizing power and the $k_F/k_{Cl}$ values are similar to those for solvolyses of n-octyl fluoroformate over the full range of solvents, suggesting that the addition step of an addition-elimination mechanism is ratedetermining. These observations are also compared with those previously reported for the corresponding chloroformate and fluoroformate esters.
Bibliography:KISTI1.1003/JNL.JAKO200802727150203
G704-000067.2008.29.9.052
ISSN:0253-2964
1229-5949