Kinetics and Mechanism of the Pyridinolysis of Diisopropyl Chlorothiophosphate in Acetonitrile 


Vol. 33,  No. 10, pp. 3203-3207, Oct.  2012
10.5012/bkcs.2012.33.10.3203


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  Abstract

The nucleophilic substitution reactions of diisopropyl chlorothiophosphate (5) with X-pyridines have been kinetically studied in MeCN at 35.0 oC. The Hammett and Brönsted plots for the substituent X variations in the nucleophiles show biphasic concave upwards with a break point at X = 3-Ph. The pyridinolysis rate of 5 exhibits great negative deviation from the Taft plot. A concerted SN2 mechanism is proposed involving a change of the attacking direction of the X-pyridines from a frontside attack with the strongly basic pyridines to a backside attack with the weakly basic pyridines.

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  Cite this article

[IEEE Style]

M. E. U. Hoque and H. W. Lee, "Kinetics and Mechanism of the Pyridinolysis of Diisopropyl Chlorothiophosphate in Acetonitrile," Bulletin of the Korean Chemical Society, vol. 33, no. 10, pp. 3203-3207, 2012. DOI: 10.5012/bkcs.2012.33.10.3203.

[ACM Style]

Md. Ehtesham Ul Hoque and Hai Whang Lee. 2012. Kinetics and Mechanism of the Pyridinolysis of Diisopropyl Chlorothiophosphate in Acetonitrile. Bulletin of the Korean Chemical Society, 33, 10, (2012), 3203-3207. DOI: 10.5012/bkcs.2012.33.10.3203.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949