Document Detail

Similarity based on atomic electrostatic potential in heterocyclic molecules: acidity of tetrazoles.
MedLine Citation:
PMID:  18785699     Owner:  NLM     Status:  MEDLINE    
The multidimensional similarity measure, operating in the space spanned by potential values, and introduced recently for benzoic acids and monosubstituted benzenes, was applied to tetrazoles, hydrogenated tetrazoles, and phenyltetrazoles. High correlation of potentials at individual atoms constituting five-membered ring in tetrazoles was also found in hydrogenated tetrazoles despite the loss of aromatic character of the latter. Quality of the similarity measure was estimated by correlating it with Hammett constants and with free energy of dissociation for tetrazoles and phenyltetrazoles and methylation reactions for tetrazoles in gas phase. The correlations with the similarity measure were likened to correlations with the potentials at corresponding single atoms in the molecules. As the latter correlations were as good as (or even better than) the correlations with the multidimensional similarity introduced previously, we propose that potentials at the nuclei of congener molecules can be used as the simplest similarity measures. In addition to other systems where potentials at single atoms (sites of binding) were proven to be good reactivity descriptors, this investigation expands their applicability over some heterocyclic systems. Particularly, when similarity of acidic molecules is quantified by the potential at the dissociating hydrogen, it is a good measure of the acid strength both in gas phase as well as in water.
Nina Sadlej-Sosnowska; Kamila Murłowska
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-09-11
Journal Detail:
Title:  The journal of physical chemistry. A     Volume:  112     ISSN:  1520-5215     ISO Abbreviation:  J Phys Chem A     Publication Date:  2008 Oct 
Date Detail:
Created Date:  2008-10-03     Completed Date:  2008-12-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9890903     Medline TA:  J Phys Chem A     Country:  United States    
Other Details:
Languages:  eng     Pagination:  10017-22     Citation Subset:  IM    
National Medicines Institute, 30/34 Chełmska Street, 00-725 Warsaw, Poland.
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MeSH Terms
Benzene / chemistry
Heterocyclic Compounds / chemistry*
Hydrogen / chemistry
Static Electricity
Tetrazoles / chemistry*
Reg. No./Substance:
0/Heterocyclic Compounds; 0/Tetrazoles; 1333-74-0/Hydrogen; 71-43-2/Benzene

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