Document Detail

Thermodynamics of the clusterization process of cis isomers of unsaturated fatty acids at the air/water interface.
MedLine Citation:
PMID:  19320525     Owner:  NLM     Status:  MEDLINE    
In the framework of the semiempirical PM3 method, the thermodynamic parameters of cis isomers of unsaturated carboxylic acids at the air/water interface are studied. The model systems used are unsaturated cis fatty acid of the composition Delta = 12-15 and omega = 6-11, where Delta and omega refer to the number of carbon atoms between the functional group and double bond, and that between the double bond and methyl group, respectively. For dimers, trimers, and tetramers of the four acid series, the thermodynamic parameters of clusterization are calculated. It is shown that the position of the double bond does not significantly affect the values of thermodynamic parameters of formation and clusterization of carboxylic acids for equal chain lengths (n = Delta + omega). The calculated results show that for cis unsaturated fatty acid with odd Delta values the spontaneous clusterization threshold corresponds to n = 17-18 carbon atoms in the alkyl chain, while for monounsaturated acids with even Delta values this threshold corresponds to n = 18-19 carbon atoms in the alkyl chain. These differences in the clusterization threshold between the acids with even and odd Delta values are attributed to the formation of additional intermolecular hydrogen bonds between the ketonic oxygen atom of one monomer and the hydrogen atom linked to the alpha-carbon atom of the second monomer for the acids with odd Delta values or between the hydroxyl oxygen atom of one monomer and hydrogen atom linked to the alpha-carbon atom of the second monomer for the acids with even Delta values. The results obtained in the study agree satisfactorily with our experimental data for cis unsaturated nervonic (Delta15, omega9) and erucic acids (Delta13, omega9), and published data for some fatty acids, namely cis-16-heptadecenoic (Delta16, omega1), cis-9-hexadecenoic (Delta7, omega9), cis-11-eicosenoic (Delta11, omega9) and cis-9-octadecenoic acid (Delta9, omega9).
Yu B Vysotsky; E A Belyaeva; V B Fainerman; D Vollhardt; E V Aksenenko; R Miller
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The journal of physical chemistry. B     Volume:  113     ISSN:  1520-6106     ISO Abbreviation:  J Phys Chem B     Publication Date:  2009 Apr 
Date Detail:
Created Date:  2009-03-26     Completed Date:  2009-06-01     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101157530     Medline TA:  J Phys Chem B     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4347-59     Citation Subset:  IM    
Donetsk National Technical University, Ukraine.
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MeSH Terms
Fatty Acids / chemistry*
Hydrogen Bonding
Models, Molecular
Molecular Conformation
Water / chemistry*
Reg. No./Substance:
0/Fatty Acids; 7732-18-5/Water

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