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Kinetics and Mechanism of Pyridinolyses of Ethyl Methyl and Ethyl Propyl Chlorothiophosphates in Acetonitrile

Authors :
Hai Whang Lee
Hasi Rani Barai
Source :
Bulletin of the Korean Chemical Society. 34:3372-3376
Publication Year :
2013
Publisher :
Korean Chemical Society, 2013.

Abstract

concave upwards with a break point at X = H (2) and 3-Ph (4), respectively. A stepwise mechanism with a ratelimiting leaving group expulsion from the intermediate is proposed based on the magnitudes of selectivity parameters for both substrates. The considerably large values of βX = 1.50(2) and 1.44(4) with strongly basic pyridines and relatively small values of βX = 0.43(2) and 0.36(4) with weakly basic pyridines are interpreted as a change of the attacking direction of the X-pyridines from a frontside to a backside attack toward the chloride leaving group.

Details

ISSN :
02532964
Volume :
34
Database :
OpenAIRE
Journal :
Bulletin of the Korean Chemical Society
Accession number :
edsair.doi...........b1479fb5b5113fb53882feda510866c1
Full Text :
https://doi.org/10.5012/bkcs.2013.34.11.3372