Kinetics and Mechanism of the Anilinolysis of Dipropyl Chlorothiophosphate in Acetonitrile

The nucleophilic substitution reactions of dipropyl chlorothiophosphate (3) with substituted anilines (XC_6H_4NH_2) and deuterated anilines (XC_6H_4ND_2) are investigated kinetically in acetonitrile at 55.0 ^oC. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are primary normal (kH/kD...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2011, 32(12), , pp.4403-4407
Main Authors: Hoque, Md. Ehtesham Ul, Lee, Hai-Whang
Format: Article
Language:English
Subjects:
화학
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Summary:The nucleophilic substitution reactions of dipropyl chlorothiophosphate (3) with substituted anilines (XC_6H_4NH_2) and deuterated anilines (XC_6H_4ND_2) 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. KCI Citation Count: 10
ISSN:0253-2964
1229-5949
DOI:10.5012/bkcs.2011.32.12.4403