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KMID : 1059519850290010015
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Journal of the Korean Chemical Society
1985 Volume.29 No. 1 p.15 ~ p.22
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Kinetic Studies of Nucleophilic Substitution Reaction of para-Substituted Benzoyl Compounds with Pyridines
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Kim Jeong-Wha
Uhm Tae-Seop
Lee Ik-Choon
Koo In-Sun
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Abstract
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Kinetic studies of nucleophilic substitution reaction of substituted benzoyl cyanides and benzoyl chlorides with pyridines were conducted at 25℃ in pure acetone solvent. Results showed that (ⅰ) magnitudes of ρS, ρN and β associated with a change of substituent in the nucleophile indicate relatively advanced bond-formation in the transition state, (ⅱ) the potential energy surface model is able to predict the reaction mechanism, but it is unable to predict the transition state variation to a more product-like transition state, where bond-formation is much more progressed than bond breaking, upon changing the leaving group to that with better leaving ability (ⅲ) the quantum mechanical model predicted the product-like transition state and slightly better leaving ability of CN- as compared with Cl-.
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KEYWORD
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