AROMATIC RINGS ACT AS HYDROGEN-BOND ACCEPTORS
AROMATIC RINGS ACT AS HYDROGEN-BOND ACCEPTORS
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DOI：
10.1016/0022-2836(88)90471-8
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发表时间：
1988-06-20
影响因子：
5.6
通讯作者：
PERUTZ, MF
中科院分区：
文献类型：
--
作者：
LEVITT, M;PERUTZ, MF
简单的能量计算表明，在氢键供体（如> NH基团）和作为氢键受体的苯环中心之间存在显著的相互作用。这种相互作用的强度约为普通氢键的一半，贡献了约3千卡/摩尔（1卡= 4.184 J）的稳定焓，有望在分子结合中发挥重要作用。有趣的是，芳香族氢键是由以环碳和氢原子为中心的小的部分电荷产生的，不需要考虑离域电子。尽管一些能量计算已经包括了这种部分电荷，但直到在蛋白质-药物复合物中观察到芳香氢键之后，人们才认识到它们在形成如此强的相互作用中的作用。
Simple energy calculations show that there is a significant interaction between a hydrogen bond donor (like the > NH group) and the centre of a benzene ring, which acts as a hydrogen bond acceptor. This interaction, which is about half as strong as a normal hydrogen bond, contributes approximately 3 kcal/mol (1 cal = 4.184 J) of stabilizing enthalpy and is expected to play a significant role in molecular associations. It is of interest that the aromatic hydrogen bond arises from small partial charges centered on the ring carbon and hydrogen atoms: there is no need to consider delocalized electrons. Although some energy calculations have included such partial charges, their role in forming such a strong interaction was not appreciated until after aromatic hydrogen bonds had been observed in protein-drug complexes.