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Ultraviolet absorption characteristics and calculated semi‐empirical parameters as chemical descriptors in multivariate modelling of polychlorinated biphenyls
Author(s) -
Andersson P.,
Haglund P.,
Rappe C.,
Tysklind M.
Publication year - 1996
Publication title -
journal of chemometrics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.47
H-Index - 92
eISSN - 1099-128X
pISSN - 0886-9383
DOI - 10.1002/(sici)1099-128x(199603)10:2<171::aid-cem416>3.0.co;2-u
Subject(s) - chemistry , ionization energy , principal component analysis , absorption spectroscopy , multivariate statistics , dipole , ultraviolet , ionization , spectral line , quantitative structure–activity relationship , steric effects , analytical chemistry (journal) , organic chemistry , materials science , stereochemistry , mathematics , statistics , optoelectronics , ion , physics , quantum mechanics , astronomy
The structural variation within the polychlorinated biphenyls (PCBs) was characterized by using principal component analysis (PCA). A multivariate model was evolved from 52 physicochemical descriptors including measured ultraviolet (UV) absorption spectra, calculated semiempirical parameters (AM1) and properties captured from the literature. Parameters calculated by using the AM1‐Hamiltonian were e.g. heat of formation, dipole moments, ionization potential and the barrier of internal rotation. The UV spectra were measured and digitized in the range 200–300 nm. The multivariate model revealed that most of the information within the set of physicochemical parameters was related to molecular size. Descriptors depending on size were e.g. GC retention times, partition coefficients and a subset of semiempirically derived energy terms. Important also were parameters reflecting differences in substitution patterns and related to electronic and steric properties, such as UV absorption in the wavelength region 245–300 nm, the barrier of internal rotation and the ionization potential. The developed model describes the large variation in physicochemical characteristics within the PCBs. The importance of a broad chemical characterization is illustrated by a quantitative structure‐activity relationship (QSAR) for the potency of inhibition of intercellular communication for 27 structurally diverse tetra‐ to heptachlorinated PCBs.