The origin of the generalized anomeric effect: possibility of CH/n and CH/π hydrogen bonds

被引：33

作者：

Takahashi, Osamu ^{[1
]}

Yamasaki, Katsuyoshi ^{[1
]}

Kohno, Yuji ^{[2
]}

Ueda, Kazuyoshi ^{[2
]}

Suezawa, Hiroko ^{[3
]}

Nishio, Motohiro ^{[4
]}

机构：

[1] Hiroshima Univ, Dept Chem, Grad Sch Sci, Higashihiroshima 7398526, Japan

[2] Yokohama Natl Univ, Dept Mat Sci, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

[3] Minist Educ Culture Sports Sci & Technol, Chiyoda Ku, Tokyo 1008959, Japan

[4] CHPI Inst, Machida, Tokyo 1940031, Japan

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 10期

关键词：

Ab initio calculation; CH/n hydrogen bond; CH/pi hydrogen bond; Gauche conformation; Nonbonded distance; NBO charge; AB-INITIO CALCULATIONS; MOLECULAR-ORBITAL THEORY; NUCLEAR-QUADRUPOLE RESONANCE; CONFORMATIONAL STABILITY; STRUCTURAL MOIETIES; INTERNAL-ROTATION; MO CALCULATIONS; VIBRATIONAL ASSIGNMENT; INFRARED-SPECTROSCOPY; ELECTRONIC-STRUCTURE;

D O I：

10.1016/j.carres.2009.04.011

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Ab initio MO calculations were carried out at the MP4/6-311++G(3df,3pd)//MP2/6-311++G(3df,3pd) level to investigate the conformational Gibbs energy of a series of methyl ethers CH3O-CH2-X (X = OH, OCH3, F, Cl, Br, CN, C CH, C6H5, CHO). It was found that the Gibbs energy of the gauche conformers is lower in every case than that of the corresponding anti conformers. In the more stable gauche conformers, the interatomic distance between X and the hydrogen atom was shorter than the sum of the van der Waals radii. The natural bonding orbital (NBO) charges of group X were more negative in the gauche conformers than in the anti conformers. We suggest that the CH/n and CH/pi hydrogen bonds play an important role in stabilizing the gauche conformation of these compounds. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1225 / 1229

页数：5

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