C. F. Bernasconi, J. Fassberg
1994
Citations
0
Influential Citations
4
Citations
Journal
Journal of the American Chemical Society
Abstract
A kinetic study of the hydrolysis of substituted α-nitrostilbenes (NS-Z with Z=4-Me, H, 4-Br, 3-NO 2 , and 4-NO 2 ) in 50% Me 2 SO-50% water (v/v) at 20 o C is reported. The mechanism consists of four steps: nucleophilic addition to NS-Z of water (k 1 H2O ) and OH - (k 1 OH ) to form PhCH(OH)C(Ar)NO 2 - (T OH - ) carbon protonation ofT OH - by water (k 2 H2O ), H 3 O + (k 2 H ), and buffer acids (k 2 BH ) to form PhCH(OH)CH(Ar)NO 2 (T OH 0 );