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- W2105875448 abstract "The aminolyses of diphenyl phosphinic chloride (1) with substituted anilines in acetonitrile at 55.0 oC are investigated kinetically. Large Hammett ρ X (ρnuc = ?4.78) and Bronsted β X (βnuc = 1.69) values suggest extensive bond formation in the transition state. The primary normal kinetic isotope effects (kH/kD = 1.42-1.82) involving deuterated aniline (XC6H4ND2) nucleophiles indicate that hydrogen bonding results in partial deprotonation of the aniline nucleophile in the rate-limiting step. The faster rate of diphenyl phosphinic chloride (1) than diphenyl chlorophosphate (2) is rationalized by the large proportion of a frontside attack in the reaction of 1. These results are consistent with a concerted mechanism involving a partial frontside nucleophilic attack through a hydrogen-bonded, four-center type transition state." @default.
- W2105875448 created "2016-06-24" @default.
- W2105875448 date "2007-06-20" @default.
- W2105875448 modified "2023-10-02" @default.
- W2105875448 title "Kinetics and Mechanism of the Aminolysis of Diphenyl Phosphinic Chloride with Anilines" @default.
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- W2105875448 doi "https://doi.org/10.5012/bkcs.2007.28.6.936" @default.
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