スクシンイミドエステルの化学 (第12報) : 有機溶媒中でのN-スクシンイミジルベンゾエートによる脂肪族第一級アミンのN-アリールカルボニル化反応の速度論的研究

概要

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The reaction of N-succinimidyl benzoates (1) with an aliphatic primary amine (2) to give the corresponding N- (arylcarbonyl) amines (3) was studied kinetically in organic solvents at 30°C. The rates roughly increased with increasing polarity (D : dielectric constant) of the solvent. The rates for meta- and para-substituted (1) correlated with the Hammet σ value, giving a positive ρ of 1.0. However, the rate for ortho-substituted (1) was less than that expected from the ionization constant of the corresponding benzoic acid and this resulted from steric hindrance of the substituent. Based on these findings, a probable mechanism involving nucleophilic attack is proposed and discussed.
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