Conformational stabilities of 1-methoxy-2-(methylthio)ethane and relevant intramolecular CH•••O interaction studied by matrix-isolation infrared spectroscopy and density functional calculations

被引：39

作者：

Harada, T ^{[1
]}

Yoshida, H ^{[1
]}

Ohno, K ^{[1
]}

Matsuura, H ^{[1
]}

机构：

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

来源：

CHEMICAL PHYSICS LETTERS | 2002年 / 362卷 / 5-6期

关键词：

D O I：

10.1016/S0009-2614(02)01139-9

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Conformational stabilities of 1-methoxy-2-(methylthio)ethane were studied by matrix-isolation infrared spectroscopy, and the relevant intramolecular 1,5-CH...O interaction was examined by density functional calculations. The conformer with trans-trans-gauche(+/-) around the CH3O-CH2-CH2-SCH3 bonds is the most stable in an argon matrix and the conformer with trans-gauche(+/-)-gauche(+/-) is the second most stable. The energy difference between the two conformers was determined to be 0.7 +/- 0.4 kJ mol(-1) using thermal effusive sources. The 1,5-CH...O interaction is responsible for the high stability of the trans-gauche(+/-)-gauche(+/-) conformer, since the nonbonded (C)H...O distance associated with this interaction is shorter than the corresponding van der Waals separation by 0.15 Angstrom. The energy of the 1,5-CH...O interaction was evaluated to be 4.0 kJ mol(-1). (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：453 / 460

页数：8

共 31 条

[1] INVESTIGATION OF THE MOLECULAR-STRUCTURE AND CONFORMATION OF 1,2-DIMETHOXYETHANE, CH3-O-CH2-CH2-O-CH3, IN THE GAS-PHASE [J].

ASTRUP, EE .

ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1979, 33 (09) :655-664

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Hydrogen bond versus anti-hydrogen bond: A comparative analysis based on the electron density topology [J].

Cubero, E ;

Orozco, M ;

Hobza, P ;

Luque, FJ .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (32) :6394-6401

[4]

Desiraju G., 1999, WEAK HYDROGEN BOND S, P29

[5] INVESTIGATION OF 1,2-DICHLOROETHANE CONFORMER EQUILIBRIA BY EFFUSIVE BEAM-MATRIX-1R SPECTROSCOPY [J].

FELDER, P .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1980, 36 (02) :223-224

[6]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V16, P01

[7] Fundamental properties of the CH•••O interaction:: Is it a true hydrogen bond? [J].

Gu, YL ;

Kar, T ;

Scheiner, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9411-9422

[8] Implications of intramolecular OH•••Se hydrogen bonding and CH•••O interaction in the conformational stabilization of 2-(methylseleno)ethanol studied by vibrational spectroscopy and density functional theory [J].

Harada, T ;

Yoshida, H ;

Ohno, K ;

Matsuura, H ;

Zhang, J ;

Iwaoka, M ;

Tomoda, S .

JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (18) :4517-4523

[9] The fluoroform•••ethylene oxide complex exhibits a C-H•••O anti-hydrogen bond [J].

Hobza, P ;

Havlas, Z .

CHEMICAL PHYSICS LETTERS, 1999, 303 (3-4) :447-452

[10] Anti-hydrogen bond between chloroform and fluorobenzene [J].

Hobza, P ;

Spirko, V ;

Havlas, Z ;

Buchhold, K ;

Reimann, B ;

Barth, HD ;

Brutschy, B .

CHEMICAL PHYSICS LETTERS, 1999, 299 (02) :180-186

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