Open AccessQuantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives
Author(s) -
Rouillé Gaël,
Jäger Cornelia,
Huisken Friedrich,
Henning Thomas,
Czerwonka Regina,
Theumer Gabriele,
Börger Carsten,
Bauer Ingmar,
Knölker HansJoachim
Publication year - 2017
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201700115
Subject(s) - polarizability , polarity (international relations) , chemistry , density functional theory , dipole , kovats retention index , quantitative structure–activity relationship , partial charge , computational chemistry , topological index , aromaticity , electronic structure , isotropy , molecular descriptor , topology (electrical circuits) , chemical physics , molecule , organic chemistry , gas chromatography , stereochemistry , chromatography , physics , quantum mechanics , mathematics , biochemistry , combinatorics , cell
Reversed‐phase high‐performance liquid chromatography (RP‐HPLC) has been carried out for a series of unsubstituted polycyclic aromatic hydrocarbons (PAHs) and the corresponding ethynyl, 1,3‐butadiynyl, and 1,3,5‐hexatriynyl derivatives. Theoretical values of the isotropic polarizability and several polarity descriptors have been computed for each compound by using semiempirical models and density functional theory (DFT), with the aim of evaluating linear functions as quantitative structure–retention relationships (QSRRs). The polarity has been described by using either the permanent electric dipole moment, the subpolarity, or a topological electronic index. Three types of partial atomic charges have been used to calculate the subpolarity and a topological index. The choice of the theoretical model, of the polarity descriptor, and of the partial atomic charges is discussed and the resulting QSRRs are compared. Calculating the retention times from the polarizability and the topological electronic index (AM1, PM3, or DFT‐B3LYP/6–31+G(d,p)) gives the best agreement with the experimental values.