Details zur Publikation

Kategorie Textpublikation
Referenztyp Zeitschriften
DOI 10.1021/ci034064f
Titel (primär) Multilinear regression and comparative molecular field analysis (CoMFA) of azo dye-fiber affinities. 2. Inclusion of solution-phase molecular orbital descriptors
Autor Schüürmann, G.; Funar-Timofei, S.
Quelle Journal of Chemical Information and Computer Sciences
Erscheinungsjahr 2003
Department OEC
Band/Volume 43
Heft 5
Seite von 1502
Seite bis 1512
Sprache englisch
Abstract For a data set with 30 direct azo dyes taken from literature, quantitative structure−activity relationship (QSAR) analyses have been performed to model the affinity of the dye molecules for the cellulose fiber. The electronic structure of the compounds was characterized using quantum chemical gas-phase (AM1) and continuum-solvation molecular orbital parameters. As regards the solution phase, COSMO appears to be better suited than SM2 in quantifying relative trends of the aqueous solvation energy. For the dye−fiber affinity, the leave-one-out prediction capability of multilinear regression equations is superior to CoMFA, with predictive squared correlation coefficients ranging from 0.63 (pure CoMFA) to 0.89. At the same time, solution-phase CoMFA is superior to previously derived AM1-based CoMFA models. As a general trend, the dye−fiber affinity increases with increasing electron donor capacity that corresponds to an increasing hydrogen bond acceptor strength of the azo dyes. The discussion includes the consideration of structural features that are likely to be involved in dye−fiber and dye−dye hydrogen bonding interactions, and possible links between CoMFA electrostatic results and the atomic charge distribution of the compounds.
dauerhafte UFZ-Verlinkung https://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=5206
Schüürmann, G., Funar-Timofei, S. (2003):
Multilinear regression and comparative molecular field analysis (CoMFA) of azo dye-fiber affinities. 2. Inclusion of solution-phase molecular orbital descriptors
J. Chem. Inf. Comp. Sci. 43 (5), 1502 - 1512 10.1021/ci034064f