Quantifying intermolecular interactions: Guidelines for the molecular recognition toolbox

被引:877
作者
Hunter, CA [1 ]
机构
[1] Univ Sheffield, Dept Chem, Krebs Inst Biomol Sci, Ctr Chem Biol, Sheffield S3 7HF, S Yorkshire, England
关键词
formation enthalpy; hydrogen bonds; molecular recognition; solvent effects; statistical thermo-dynamics;
D O I
10.1002/anie.200301739
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Molecular recognition events in solution are affected by many different factors that have hampered the development of an understanding of intermolecular interactions at a quantitative level. Our tendency is to partition these effects into discrete phenomenological fields that are classified, named, and divorced: aromatic interactions, cation-π interactions, CH-O hydrogen bonds, short strong hydrogen bonds, and hydrophobic interactions to name a few. To progress in the field, we need to develop an integrated quantitative appreciation of the relative magnitudes of all of the different effects that might influence the molecular recognition behavior of a given system. In an effort to navigate undergraduates through the vast and sometimes contradictory literature on the subject, I have developed an approach that treats theoretical ideas and experimental observations about intermolecular interactions in the gas phase, the solid state, and solution from a single simplistic viewpoint. The key features are outlined here, and although many of the ideas will be familiar, the aim is to provide a semiquantitative thermodynamic ranking of these effects in solution at room temperature.
引用
收藏
页码:5310 / 5324
页数:15
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