The origin of the generalized anomeric effect: possibility of CH/n and CH/pi hydrogen bonds
Carbohydrate Research Volume 344 Issue 10
Page 1225-1229
published_at 2009
アクセス数 : 1108 件
ダウンロード数 : 262 件
今月のアクセス数 : 2 件
今月のダウンロード数 : 2 件
この文献の参照には次のURLをご利用ください : https://ir.lib.hiroshima-u.ac.jp/00027773
| File | |
| Title ( eng ) |
The origin of the generalized anomeric effect: possibility of CH/n and CH/pi hydrogen bonds
|
| Creator |
Kohno Yuji
Ueda Kazuyoshi
Suezawa Hiroko
Nishio Motohiro
|
| Source Title |
Carbohydrate Research
|
| Volume | 344 |
| Issue | 10 |
| Start Page | 1225 |
| End Page | 1229 |
| Abstract |
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.
|
| Keywords |
Ab initio calculation
CH/n hydrogen bond
CH/n hydrogen bond
Gauche conformation
Nonbonded distance
NBO charge
|
| NDC |
Chemistry [ 430 ]
|
| Language |
eng
|
| Resource Type | journal article |
| Publisher |
Elsevier Sci Ltd
|
| Date of Issued | 2009 |
| Rights |
Copyright (c) 2009 Elsevier Ltd
|
| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0008-6215
[DOI] 10.1016/j.carres.2009.04.011
[NCID] AA00598932
[DOI] http://dx.doi.org/10.1016/j.carres.2009.04.011
|
