Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules

被引：702

作者：

Bouchy, A ^{[1
]}

Rinaldi, D ^{[1
]}

Rivail, JL ^{[1
]}

机构：

[1] Univ Nancy 1, CNRS, UMR 7565, Equipe Chim & Biochim Theor, F-54506 Vandoeuvre Les Nancy, France

来源：

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY | 2004年 / 96卷 / 03期

关键词：

density functional theory; intramolecular hydrogen bonds; push-pull conjugated molecules; solvent effect;

D O I：

10.1002/qua.10569

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：

A series of molecules leading to resonance-assisted hydrogen bonding has been investigated by means of Becke's three-parameter functional and the gradient-corrected functional of Lee, Yang, and Parr/6-311G(d,p) computations. The solvent (carbon tetrachloride) is simulated by the self-consistent reaction field model. The influence of the molecular structure on the intramolecular proton transfer is analyzed. The effect of the solvent on the geometry of the hydrogen bonds and on the frequency of the stretching modes of the groups involved in these bonds is noticeable. A linear relationship between the vibrational frequency and the bond length is found. (C) 2003 Wiley Periodicals, Inc.

引用

页码：273 / 281

页数：9

共 27 条

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

BECKE, AD .

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

[2] Ab initio study of 2,4-dihalosubstituted malonaldehyde and 2-halo-phenols in gas phase and solution [J].

Buemi, G .

CHEMICAL PHYSICS, 2002, 277 (03) :241-256

[3] Ab initio study of tautomerism and hydrogen bonding of β-carbonylamine in the gas phase and in water solution [J].

Buemi, G ;

Zuccarello, F ;

Venuvanalingam, P ;

Ramalingam, M .

THEORETICAL CHEMISTRY ACCOUNTS, 2000, 104 (3-4) :226-234

[4] LIQUID-STATE QUANTUM-CHEMISTRY - AN IMPROVED CAVITY MODEL [J].

DILLET, V ;

RINALDI, D ;

RIVAIL, JL .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (19) :5034-5039

[5] Analytical energy derivatives for a realistic continuum model of solvation: Application to the analysis of solvent effects on reaction paths [J].

Dillet, V ;

Rinaldi, D ;

Bertran, J ;

Rivail, JL .

JOURNAL OF CHEMICAL PHYSICS, 1996, 104 (23) :9437-9444

[6] REACTION FIELD FACTORS FOR A MULTIPOLE DISTRIBUTION IN A CAVITY SURROUNDED BY A CONTINUUM [J].

DILLET, V ;

RINALDI, D ;

ANGYAN, JG ;

RIVAIL, JL .

CHEMICAL PHYSICS LETTERS, 1993, 202 (1-2) :18-22

[7]

FRISCH MJ, 2002, GAUSSIAN 98 REVISION, V4

[8] EVIDENCE FOR RESONANCE-ASSISTED HYDROGEN-BONDING FROM CRYSTAL-STRUCTURE CORRELATIONS ON THE ENOL FORM OF THE BETA-DIKETONE FRAGMENT [J].

GILLI, G ;

BELLUCCI, F ;

FERRETTI, V ;

BERTOLASI, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1023-1028

[9] Evidence for intramolecular N-H•••O resonance-assisted hydrogen bonding in β-enaminones and related heterodienes.: A combined crystal-structural, IR and NMR spectroscopic, and quantum-mechanical investigation [J].

Gilli, P ;

Bertolasi, V ;

Ferretti, V ;

Gilli, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10405-10417

[10] COVALENT NATURE OF THE STRONG HOMONUCLEAR HYDROGEN-BOND - STUDY OF THE O-H---O SYSTEM BY CRYSTAL-STRUCTURE CORRELATION METHODS [J].

GILLI, P ;

BERTOLASI, V ;

FERRETTI, V ;

GILLI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :909-915

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