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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 12
BKCSDE 32(12)
December 20, 2011 

Kinetics and Mechanism of the Anilinolysis of Dipropyl Chlorothiophosphate in Acetonitrile
Md. Ehtesham Ul Hoque, Hai Whang Lee *
Phosphoryl transfer reaction, Anilinolysis, Dipropyl chlorothiophosphate, Deuterium kinetic isotope effect, Steric effect
The nucleophilic substitution reactions of dipropyl chlorothiophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 oC. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are primary normal (kH/kD = 1.11-1.35). A concerted mechanism involving predominant frontside nucleophilic attack is proposed on the basis of the primary normal DKIEs and selectivity parameters. Hydrogen bonded, four-center-type transition state is proposed. The steric effects of the two ligands on the anilinolysis rates of various substrates are discussed.
4403 - 4407
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