Saccharide-accelerated hydrolysis of boronic acid imines
Saccharide-accelerated hydrolysis of boronic acid imines
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硼酸亚胺的糖加速水解
DOI：
10.1039/b202793c
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发表时间：
2002
影响因子：
3.3
通讯作者：
T. James
中科院分区：
文献类型：
--
作者：
J. Hartley;M. Phillips;T. James
本文合成了二十种取代的N-亚苄基苯胺衍生物，并研究了它们的动力学行为。硼酸亚胺的水解速率被发现通过添加糖而加速。仅在硼酸的pKa以下观察到催化活性。改变糖的浓度或类型揭示了布朗斯台德样的线性自由能关系，表明分子内的一般酸催化作用。构效关系研究表明，该系统的电子需求是独立的硼酸部分。
Twenty substituted N-benzylidineaniline derivatives have been synthesised and their kinetic behaviour investigated. The rate of hydrolysis of the boronic acid imines was found to be accelerated by added saccharide. Catalytic activity was only observed below the pKa of the boronic acid. Altering the concentration or type of saccharide revealed a Bronsted-like linear free energy relationship, indicating that intramolecular general acid catalysis was operating. Structure–activity relationship studies demonstrated that the system's electronic demands were independent of the boronic acid moiety.