Electronic substituent effects in the nitrilase-catalyzed hydrolysis of para-substituted benzyl cyanides

S Geresh, Y Giron, Y Gilboa, R Glaser

Index: Geresh, Shimona; Giron, Yakir; Gilboa, Ygal; Glaser, Robert Tetrahedron, 1993 , vol. 49, # 44 p. 10099 - 10102

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Citation Number: 9

Abstract

The initial rates of the nitrilase (Novo)-catalyzed hydrolysis of a series of para-substituted benzyl cyanides (R= NO2, Cl, OCH3, OH, NH2) were found to be susceptible to the nature of the para-substituent of the substrate and a Hammett-type linear free energy correlation was observed with ϱ= 0.96. In a separate study, effective solubilization of substituted benzyl cyanide substrates having electron-donating groups (OH, NH2, OCH3) was achieved ...