Document Detail


Energetics and structural properties, in the gas phase, of trans-hydroxycinnamic acids.
MedLine Citation:
PMID:  22316076     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
We have studied the energetics and structural properties of trans-cinnamic (CA), o-, m-, p-coumaric (2-, 3-, 4-hydroxycinnamic), caffeic (3,4-dihydroxycinnamic), ferulic (4-hydroxy-3-methoxycinnamic), iso-ferulic (3-hydroxy-4-methoxycinnamic) and sinapic (3,5-dimethoxy-4-hydroxycinnamic) acids. The experimental values of (g), determined (in kJ•mol-1) for CA (-229.8 ± 1.9), p-coumaric (-408.0 ± 4.4), caffeic (-580.0 ± 5.9) and ferulic (-566.4 ± 5.7) acids, allowed us to derive (g) of o-coumaric (-405.6 ± 4.4), m-coumaric (-406.4 ± 4.4), iso-ferulic (-565.2 ± 5.7) and sinapic (-698.8 ± 4.1) acids. From these values, and using isodesmic/homodesmotic reactions, we studied the energetic effects of Π-donor substituents (-OH and -OCH3) in cinnamic acid derivatives and in the respective benzene analogues. Our results indicate that the interaction between -OCH3 and/or -OH groups in hydroxycinnamic acids takes place without significant influence of the propenoic fragment.
Authors:
Juan Zenon Davalos; Antonio Chana; Andrés Guerrero; Rebeca Herrero
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-2-8
Journal Detail:
Title:  The journal of physical chemistry. A     Volume:  -     ISSN:  1520-5215     ISO Abbreviation:  -     Publication Date:  2012 Feb 
Date Detail:
Created Date:  2012-2-9     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9890903     Medline TA:  J Phys Chem A     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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