Evolution of Quantum Similarity Measures: How They Perform in Modeling Hammett Constants

Sadlej-Sosnowska, N.

Artykuł - szczegóły

Tytuł artykułu

Evolution of Quantum Similarity Measures: How They Perform in Modeling Hammett Constants

Autorzy

Sadlej-Sosnowska N.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

This study was aimed at comparing a few measures of similarity of carboxylic acids’ molecules, based on the electronic descriptors derived from molecular wave functions. Five series of molecules were investigated: benzoic acids, thiophene-2-carboxylic acids, furane-2-carboxylic acids, trans-cinnamic acids, and 3-phenylpropionic acids. It has been previously found that in stead of comparing densities or other electronic properties of the entire molecules, it is sufficient to use the properties within a molecular fragment, active towards a given reaction. In this vein, three measures have been compared: the one pertaining to the properties of bond critical points, the one derived from atomic potentials, and that based on Fermi-hole densities, confined to the COOH group. Never the less, it appeared that other ways of defining a similarity measure may also be practical, namely that based on charges of the COOH group and that based on the properties of another molecular fragment, i.e. the substituent and the ring carbon atom connected to the so-called substituent active region. The calculations were carried out at the B3LYP/cc-pVDZ level.

Słowa kluczowe

similarity substituent active region atomic electrostatic potential bond critical point Fermi hole carboxylic acids

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2009

Tom

Vol. 83, nr 12

Strony

2215--2224

Opis fizyczny

Bibliogr. 54 poz., rys.

Twórcy

autor

Sadlej-Sosnowska N.

National Medicines Institute, 30/34 Chełmska Street, 00-725 Warsaw, Poland phone: +48 22 841 94 35 ext.348, sadlej@il.waw.pl

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Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ7-0016-0031