The Journal of Organic Chemistry

Kinetics of reversible thiolate ion addition to substituted. beta.-nitrostyrenes in water. Radicaloid transition state or principle of nonperfect synchronization?

CF Bernasconi, DF Schuck

Index: Bernasconi, Claude F.; Schuck, David F. Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2365 - 2373

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Citation Number: 30

Abstract

The kinetics of reversible nucleophilic thiolate ion (RS-with R= n-Bu, HOCH2CH2, Me02CCH2CH2 and Me02CCH2) addition to Z-substituted 8-nitrostyrenes (Z= 4-Me2N, 4- Me0, 4-MeS, 4-Me, H, 3-C1, 4-C1, 3-CN, 4-CN, and% No2), to form ArCH (RS) CH= NO;, have been measured in water at 20" C. Rate constants in the forward (k,) and reverse direction (k-,) and equilibrium constants (K,) correlate reasonably well with Hammett a- ...