The stabilizing role of intramolecular hydrogen bonding in disubstituted hydroxy-quinones

A voltammetric and theoretical study of a series of quinone derivatives in the presence and absence of hydroxyl groups as substituents is presented. The results indicate that intramolecular hydrogen bonding results in stabilization of the anion radical structure, leading to a shift in potential valu...

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Bibliographic Details
Published inElectrochimica acta Vol. 110; pp. 628 - 633
Main Authors Armendáriz-Vidales, Georgina, Martínez-González, Eduardo, Cuevas-Fernández, Héctor Javier, Fernández-Campos, Didier Omar, Burgos-Castillo, Rutely C., Frontana, Carlos
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.11.2013
Subjects
Anions
BHandHLYP functional
Conformational analysis
Cyclic voltammetry
Density functional theory
Derivatives
Hydrogen bonding
Hydrogen bonds
Hydroxyquinone
Intramolecular hydrogen bond
Quinones
Radicals
Stabilization
Cyclic voltammetry
Hydroxyquinone
Intramolecular hydrogen bond
BHandHLYP functional
Conformational analysis
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Summary:A voltammetric and theoretical study of a series of quinone derivatives in the presence and absence of hydroxyl groups as substituents is presented. The results indicate that intramolecular hydrogen bonding results in stabilization of the anion radical structure, leading to a shift in potential values for these derivatives toward less negative potentials compared with the unsubstituted quinones. A detailed analysis of the experimental responses reveals that no more coupled chemical reactions must be considered to explain the obtained data. The role of the stabilization of the electrogenerated radical anion by delocalization of the added electron within the structure is discussed on the basis of theoretical results employing density functional theory and the Truhlar model for solvation; also, estimates of the intramolecular hydrogen bond energy are presented.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0013-4686
1873-3859
DOI:10.1016/j.electacta.2013.05.123