Application of the NT solvent nucleophilicity scale to attack at phosphorus: Solvolyses of N, N, N', N'-tetramethyldiamidophosphorochloridate

DN Kevill, B Miller

Index: Kevill, Dennis N.; Miller, Bronwyn Journal of Organic Chemistry, 2002 , vol. 67, # 21 p. 7399 - 7406

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Citation Number: 51

Abstract

The specific rates of solvolysis of N, N, N', N'-tetramethyldiamidophosphorochloridate have been measured at 25.0° C in 31 solvents. Analysis with the extended Grunwald-Winstein equation leads to sensitivities toward changes in solvent nucleophilicity (l) of 1.20±0.07 and toward changes in solvent ionizing power (m) of 0.69±0.04. The correlation is improved by omission of the four data points for 2, 2, 2-trifluoroethanol-ethanol mixtures (F-test value ...