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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 3
BKCSDE 35(3)
March 20, 2014 

Kinetics and Mechanism of the Anilinolysis of Aryl N,N-Dimethyl Phosphoroamidochloridates in Acetonitrile
Hasi Rani Barai, Hai Whang Lee*
Phosphoryl transfer reaction, Anilinolysis, Aryl N,N-dimethyl phosphoroamidochloridates, Deuterium kinetic isotope effects, Cross-interaction constant
The nucleophilic substitution reactions of Y-aryl N,N-dimethyl phosphoroamidochloridates with substituted anilines and deuterated anilines are kinetically investigated in acetonitrile at 65.0 oC. A stepwise mechanism with a rate-limiting leaving group departure from the intermediate is proposed based on the positive ρXY value. The deuterium kinetic isotope effects involving deuterated anilines show secondary inverse with all the nucleophiles, rationalized by a dominant backside nucleophilic attack.
753 - 757
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