Electrophilicity of quinones and its relationship with hydride affinity

被引：23

作者：

Campodonico, Paola R. ^{[1
]}

Aizman, Arie ^{[3
]}

Contreras, Renato ^{[2
]}

机构：

[1] Univ Desarrollo, Clin Alemana, Fac Med, Inst Ciencias, Santiago, Chile

[2] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

[3] Univ Fed Santa Maria, Dept Quim, Valparaiso, Chile

来源：

CHEMICAL PHYSICS LETTERS | 2009年 / 471卷 / 1-3期

关键词：

PERSPECTIVES; PREDICTION; HARDNESS; ORIGIN;

D O I：

10.1016/j.cplett.2009.02.015

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：

In this Letter we show that the electrophilicity index assesses well the hydride affinity ( HA) order of quinones established for a limited number of cases experimentally observed. Further comparisons with predicted HA values for a larger data base suggest that both the electrophilicity index and HA are tightly related quantities. Furthermore, electrophilic activation/deactivation patterns induced by electron-withdrawing and electron-donating groups may be consistently accounted for by the model. These results open the possibility of predicting HA for quinones not evaluated experimentally up to date. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：168 / 173

页数：6

共 34 条

[1] The physical basis of the hard/soft acid/base principle [J].

Ayers, Paul W. .

FARADAY DISCUSSIONS, 2007, 135 :161-190

[2] Perturbative perspectives on the chemical reaction prediction problem [J].

Ayers, PW ;

Anderson, JSM ;

Bartolotti, LJ .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2005, 101 (05) :520-534

[3] Glutamyl substrate-induced exposure of a free cysteine residue in the vitamin K-dependent γ-glutamyl carboxylase is critical for vitamin K epoxidation [J].

Bouchard, BA ;

Furie, B ;

Furie, BC .

BIOCHEMISTRY, 1999, 38 (29) :9517-9523

[4] Structure-reactivity relationships for electrophilic sugars in interaction with nucleophilic biological targets [J].

Campodonico, Paola R. ;

Contreras, Renato .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) :3184-3190

[5] Energetics of multistep versus one-step hydride transfer reactions of reduced nicotinamide adenine dinucleotide (NADH) models with organic cations and p-quinones [J].

Cheng, JP ;

Lu, Y ;

Zhu, XQ ;

Mu, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6108-6114

[6] FREE-ENERGY HYDRIDE AFFINITIES OF QUINONES IN DIMETHYL-SULFOXIDE SOLUTION [J].

CHENG, JP ;

HANDOO, KL ;

XUE, JY ;

PARKER, VD .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5050-5054

[7]

Chermette H, 1999, J COMPUT CHEM, V20, P129, DOI 10.1002/(SICI)1096-987X(19990115)20:1<129::AID-JCC13>3.0.CO

[8]

2-A

[9] ALPHA-EFFECT .5. KINETIC AND THERMODYNAMIC NATURE OF ALPHA-EFFECT FOR AMINE NUCLEOPHILES [J].

DIXON, JE ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) :2052-&

[10] A defect in coenzyme Q biosynthesis is responsible for the respiratory deficiency in Saccharomyces cerevisiae abc1 mutants [J].

Do, TQ ;

Hsu, AY ;

Jonassen, T ;

Lee, PT ;

Clarke, CF .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (21) :18161-18168

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