Levitt M, Perutz M F
MRC Laboratory of Molecular Biology, Cambridge, England.
J Mol Biol. 1988 Jun 20;201(4):751-4. doi: 10.1016/0022-2836(88)90471-8.
Simple energy calculations show that there is a significant interaction between a hydrogen bond donor (like the greater than 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 centred 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.
简单的能量计算表明，氢键供体（如大于NH基团）与作为氢键受体的苯环中心之间存在显著相互作用。这种相互作用的强度约为正常氢键的一半，贡献了约3千卡/摩尔（1卡 = 4.184焦耳）的稳定焓，预计在分子缔合中起重要作用。有趣的是，芳香氢键源于以环碳原子和氢原子为中心的小部分电荷：无需考虑离域电子。尽管一些能量计算已包含此类部分电荷，但直到在蛋白质 - 药物复合物中观察到芳香氢键之后，才认识到它们在形成这种强相互作用中的作用。
