A theoretical study on bond dissociation energies and oxidation potentials of monolignols

被引：24

作者：

Wei, K ^{[1
]}

Luo, SW ^{[1
]}

Fu, Y ^{[1
]}

Liu, L ^{[1
]}

Guo, QX ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Anhua 230026, Peoples R China

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2004年 / 712卷 / 1-3期

基金：

中国国家自然科学基金;

关键词：

bond dissociation energy; ionization potential; oxidation potential; lignin; biosynthesis; monolignol;

D O I：

10.1016/j.theochem.2004.10.032

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：

Density functional theory methods were utilized to study the redox reactivities of a number of monolignols. A large number of bond dissociation energies, gas-phase ionization potentials, and aqueous oxidation potentials were obtained, which compared favorably with the available experimental data. The structure-activity relationships for these quantities were investigated. The implications of these data to the biosynthesis of lignins were also discussed. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：197 / 205

页数：9

共 43 条

[1] Theoretical calculation of accurate absolute and relative gas- and liquid-phase O-H bond dissociation enthalpies of 2-mono- and 2,6-disubstituted phenols, using DFT/B3LYP [J].

Bakalbassis, EG ;

Lithoxoidou, AT ;

Vafiadis, AP .

JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (41) :8594-8606

[2] A new definition of cavities for the computation of solvation free energies by the polarizable continuum model [J].

Barone, V ;

Cossi, M ;

Tomasi, J .

JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3210-3221

[3] Enantioselective synthesis of a benzofuranic neolignan by oxidative coupling [J].

Bolzacchini, E ;

Brunow, G ;

Meinardi, S ;

Orlandi, M ;

Rindone, B ;

Rummakko, P ;

Setala, H .

TETRAHEDRON LETTERS, 1998, 39 (20) :3291-3294

[4] Oxidative degradation of monomeric and dimeric phenylpropanoids: reactivity and mechanistic investigation [J].

Canevali, C ;

Orlandi, M ;

Pardi, L ;

Rindone, B ;

Scotti, R ;

Sipila, J ;

Morazzoni, F .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (15) :3007-3014

[5] The bleaching and photostabilization of high-yield pulp by sulfur compounds .1. Reaction of thioglycerol with model quinones [J].

Cole, BJW ;

Zhou, C ;

Fort, RC .

JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 1996, 16 (04) :381-403

[6] Poly methoxy phenols in solution: O-H bond dissociation enthalpies, structures, and hydrogen bonding [J].

de Heer, MI ;

Korth, HG ;

Mulder, P .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :6969-6975

[7] A density functional theory study of coniferyl alcohol intermonomeric cross linkages in lignin - Three-dimensional structures, stabilities and the thermodynamic control hypothesis [J].

Durbeej, B ;

Eriksson, LA .

HOLZFORSCHUNG, 2003, 57 (02) :150-164

[8] Formation of β-o-4 lignin models -: A theoretical study [J].

Durbeej, B ;

Eriksson, LA .

HOLZFORSCHUNG, 2003, 57 (05) :466-478

[9] Spin distribution in dehydrogenated coniferyl alcohol and associated dilignol radicals [J].

Durbeej, B ;

Eriksson, LA .

HOLZFORSCHUNG, 2003, 57 (01) :59-61

[10] Correlation of experimental and ab initio 13C-NMR chemical shifts for monomeric lignin model compounds [J].

Elder, T .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2000, 505 :257-267

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