Correlations of Charges of Substituent Active Region in C-substituted Tetrazoles with Their Gas-phase Acidity, Hammett Constants, and Charge Distribution in Tetrazolic Rings

Sadlej-Sosnowska, N.; Murłowska, K.

Artykuł - szczegóły

Tytuł artykułu

Correlations of Charges of Substituent Active Region in C-substituted Tetrazoles with Their Gas-phase Acidity, Hammett Constants, and Charge Distribution in Tetrazolic Rings

Autorzy

Sadlej-Sosnowska N. , Murłowska K.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

Electron distribution was investigated in molecules of 5C-substituted tetrazoles by means of Natural Population Analysis. The analysis of the impact of substituents on the excess of p electrons in the ring and on the uniformity of their distribution produced similar results as were recently reported for derivatives of p-benzoic acid. The significant correlation coefficients of the two properties with the Hammett constants have been found. The more uniform the p electron distribution, measured by means of standard deviation of p electrons amounts localized on individual atoms in the ring, the more acidic is the molecule. On the other hand, an increase of the p electron number in the ring brings about an opposite effect. No correlation was found between the substituent charges and the Hammett constants. However, a new variable, namely charge of the substituent active region, composed of charge of a substituent added to charge of the ring Cipso atom, was highly correlated with the Hammett constants, as well as with charge of acidic hydrogen of the >N-H group. The results prove that the set of charges of the substituent active region may be perceived as a theoretical equivalent of the experimental set of Hammett constants and that it is closely related to properties of this group of compounds.

Słowa kluczowe

tetrazoles substituents Hammett constants gas-phase acidity charge distribution Natural Population Analysis substituent active region

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2008

Tom

Vol. 82, nr 4

Strony

935--945

Opis fizyczny

Bibliogr. 66 poz., rys.

Twórcy

autor

Sadlej-Sosnowska N.

autor

Murłowska K.

National Medicines Institute, 30/34 Chełmska Street, 00-725 Warsaw, Poland, sadlej@il.waw.pl

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ6-0024-0104