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ID 27773
file
creator
Kohno, Yuji
Ueda, Kazuyoshi
Suezawa, Hiroko
Nishio, Motohiro
subject
Ab initio calculation
CH/n hydrogen bond
CH/n hydrogen bond
Gauche conformation
Nonbonded distance
NBO charge
NDC
Chemistry
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.
journal title
Carbohydrate Research
volume
Volume 344
issue
Issue 10
start page
1225
end page
1229
date of issued
2009
publisher
Elsevier Sci Ltd
issn
0008-6215
ncid
publisher doi
language
eng
nii type
Journal Article
HU type
Journal Articles
DCMI type
text
format
application/pdf
text version
author
rights
Copyright (c) 2009 Elsevier Ltd
relation url
department
Graduate School of Science