The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates
The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates
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DOI：
10.1039/c1cp20404a
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发表时间：
2011-01-01
影响因子：
3.3
通讯作者：
Nishio, Motohiro
中科院分区：
文献类型：
--
作者：
Nishio, Motohiro
CH/π氢键是发生在软酸和软碱之间的吸引分子力。在涉及脂肪族或芳香族CH基团的典型情况下，分散能的贡献很重要。与其他弱氢键相比，库仑能是次要的。然而，这种力的氢键性质已被AIM分析证实。CH/π氢键的双重特性是这种力在化学的各个领域普遍存在的基础。一个显著的特征是CH/π氢键协同工作。另一个重要的点是，它在非极性以及极性质子溶剂如水中工作。相互作用能取决于分子片段、CH以及π-基团的性质：CH基团的质子供给能力越强，稳定作用越大。这一观点的重点是在有机化合物和超分子化学的构象这种分子力的后果。CH/π氢键的含义延伸到有机反应、聚合物科学、表面现象和涉及蛋白质的相互作用中的分子识别或选择性的特异性。许多至今尚未解决的问题，将在CH/pi范式的光照下变得更加清晰。
The CH/pi hydrogen bond is an attractive molecular force occurring between a soft acid and a soft base. Contribution from the dispersion energy is important in typical cases where aliphatic or aromatic CH groups are involved. Coulombic energy is of minor importance as compared to the other weak hydrogen bonds. The hydrogen bond nature of this force, however, has been confirmed by AIM analyses. The dual characteristic of the CH/pi hydrogen bond is the basis for ubiquitous existence of this force in various fields of chemistry. A salient feature is that the CH/pi hydrogen bond works cooperatively. Another significant point is that it works in nonpolar as well as polar, protic solvents such as water. The interaction energy depends on the nature of the molecular fragments, CH as well as pi-groups: the stronger the proton donating ability of the CH group, the larger the stabilizing effect. This Perspective focuses on the consequence of this molecular force in the conformation of organic compounds and supramolecular chemistry. Implication of the CH/pi hydrogen bond extends to the specificity of molecular recognition or selectivity in organic reactions, polymer science, surface phenomena and interactions involving proteins. Many problems, unsettled to date, will become clearer in the light of the CH/pi paradigm.