| Antioxidant activity of phenolic and related compounds: a density functional theory study on the O-H bond dissociation enthalpy. | |
| | |
MedLine Citation:
|
PMID: 15606979 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
We report here on calculations at the hybrid DFT/HF (B3-LYP/6-31G(d, p)) level of the O-H bond dissociation enthalpy (O-H BDE) of phenylpropenoic acids (caffeic, ferulic, p-coumaric and cinnamic) and phenolic acids and related compounds (gallic, methylgallate, vanillic and gentisic) in order to gain insight into the understanding of structure-antioxidant activity relationships. The results were correlated and discussed mainly on the basis of experimental data in a companion work (Galato D, Giacomelli C, Ckless K, Susin MF, Vale RMR, Spinelli A. Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity. Redox Report 2001; 6: 243-250). The O-H BDE values showed remarkable dependence on the hydroxyl position in the benzene ring and the existence of additional interaction due to hydrogen bonding. For parent molecules, the experimental antioxidant activity (AA) order was properly obeyed only when intramolecular hydrogen bonding was present in the radicalized structures of o-dihydroxyl moieties. In structurally related compounds, excellent correlation with experimental data was in general observed (0.64 < rho < 0.99). However, it is shown that excellent correlation can also be obtained for this series of compounds considering p-radicalized structures which were not stabilized by intramolecular hydrogen bonding, but this had no physical meaning. These findings suggested that the antioxidant activity evaluation of phenolic and related compounds must take into consideration the characteristics of each particular compound. |
| | |
Authors:
|
Cristiano Giacomelli; Fabio da Silva Miranda; Norberto Sanches Gonçalves; Almir Spinelli |
Related Documents
:
|
12532299 - Substituent effects on o--h bond dissociation enthalpies and ionization potentials of c... 8281579 - Design and syntheses of a series of novel serotonin3 antagonists. 9459009 - Quantitative structure-activity studies of octopaminergic 2-(arylimino)thiazolidines an... 16563449 - Synthesis of 7alpha-substituted derivatives of 17beta-estradiol. 23681489 - Complete photochromic structural changes in ruthenium(ii)diimine complexes, based on... 17002889 - Three-dimensional quantitative structure: activity relationship studies on diverse stru... 21345719 - In situ ftir spectroscopic study of the effect of co(2) sorption on h-bonding in peg-pv... 21899319 - Crystallographic snapshots of tyrosine phenol-lyase show that substrate strain plays a ... 17002359 - Synthesis and solution- and solid-state characterization of gold(i) rings with short au... |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: Redox report : communications in free radical research Volume: 9 ISSN: 1351-0002 ISO Abbreviation: Redox Rep. Publication Date: 2004 |
Date Detail:
|
Created Date: 2004-12-20 Completed Date: 2005-05-12 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 9511366 Medline TA: Redox Rep Country: England |
Other Details:
|
Languages: eng Pagination: 263-9 Citation Subset: IM |
Affiliation:
|
Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Antioxidants
/
chemistry*,
pharmacology Caffeic Acids / chemistry Chromans / pharmacology Cinnamates / chemistry Coumaric Acids / chemistry Electrochemistry Gallic Acid / analogs & derivatives*, chemistry Gentisates / chemistry Hydrogen Bonding Hydroxybenzoic Acids / chemistry*, pharmacology* Models, Chemical Oxygen / chemistry Phenol Software Structure-Activity Relationship Thermodynamics Vanillic Acid / chemistry |
| Chemical | |
Reg. No./Substance:
|
0/Antioxidants; 0/Caffeic Acids; 0/Chromans; 0/Cinnamates; 0/Coumaric Acids; 0/Gentisates; 0/Hydroxybenzoic Acids; 108-95-2/Phenol; 121-34-6/Vanillic Acid; 149-91-7/Gallic Acid; 29656-58-4/phenolic acid; 331-39-5/caffeic acid; 3934-84-7/3-O-methylgallic acid; 490-79-9/2,5-dihydroxybenzoic acid; 56305-04-5/6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; 621-82-9/cinnamic acid; 7400-08-0/4-coumaric acid; 7782-44-7/Oxygen |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Carnivorous pitcher plant uses free radicals in the digestion of prey.
Next Document: Modulation of NADP(+)-dependent isocitrate dehydrogenase in aging.