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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 9
BKCSDE 32(9)
September 20, 2011 

Kinetics and Mechanism of the Anilinolysis of Diisopropyl Chlorophosphate in Acetonitrile
Md. Ehtesham Ul Hoque, Hai Whang Lee *
Phosphoryl transfer reaction, Anilinolysis, Diisopropyl chlorophosphate, Deuterium kinetic isotope effect
The nucleophilic substitution reactions of diisopropyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 oC. The anilinolysis rate of 3 is rather slow to be rationalized by the conventional stereoelectronic effects. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.71-0.95) with maximum magnitude at X = H. A concerted mechanism involving predominant backside nucleophilic attack is proposed on the basis of the secondary inverse DKIEs.
3245 - 3250
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