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KMID : 1059519870310020123
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Journal of the Korean Chemical Society
1987 Volume.31 No. 2 p.123 ~ p.132
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Theoretical Studies on the Nucleophilic Substitution Reaction of Methyl Thiocyanate
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Lee Ik-Choon
Song Chang-Hyun
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Abstract
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Nucleophilic substitution reactions of methylthiocyanate(MTC) with anion nucleophiles, SH-, CN- and OH-, have been investigated using MNDO method. For the three reaction centers of MTC, gas-phase and solution-phase selectivities are discussed for each nucleophile by considering potential energy profiles calculated(intrinsic term) and magnitudes of negative charge on the nucleophile at the transition state(solvation term). It was found that both components of the selectivity for SH- agreed with the experimental results obtained for 4-methylbenzylthiocyanate (4-MBTC), but the selectivity order for CN- was found to agree only with that of the intrinsic term and that of OH- disagreed with any theoretical selectivity order. The MNDO optimized geometries for all species at the stationary points are reported.
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KEYWORD
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