Features of sorption of alkyl derivatives of benzimidazole under gas chromatography conditions
Abstract
The article is devoted to the study of the chromatographic behaviour of benzimidazole derivatives. The purpose of the study was to investigate the patterns of sorption of alkyl derivatives of benzimidazole under gas chromatography conditions. Polymethylsiloxane HP 5ms was used as a sorbent. Based on the obtained values of logarithmic retention indices and differential molar free energy of sorption heterocycles for the selected analysis conditions, the influence of the structure of the molecules of the studied substances on the characteristics of their retention was analysed. It was found that the studied compounds generally elute in order of the enlargement of their molecules, as well as in accordance with the change in their polarizability and lipophilicity. The influence of the position of the substituent in the main benzimidazole ring and the features of the electronic structure of heterocycle molecules on their sorption under gas chromatography conditions was studied. It has been shown that not only electronic and physicochemical parameters (volume, polarizability, lipophilicity), but also the number and position of hydrocarbon radicals and substituents included in the molecule, their nature and relative arrangement, have a significant impact on sorption.
It was established that the absence of a strict linear relationship between the retention characteristics and the physicochemical parameters of the studied compounds is associated with the structural features of their molecules. The main fragment that determines chromatographic retention is the bulky benzimidazole core, involved in dispersion interactions with the stationary phase, while the presence of a heteroatom in the sorbate molecule is the most important factor determining the sorption characteristics of substituted heterocycles. At the same time, the increase in RI was facilitated by the elongation of the hydrocarbon radical in the substituent or the replacement of the alkyl radical by phenyl.
The results of the study can be useful both from a practical point of view, for the development of methods and optimization of the analysis of compounds with similar structures, and from a theoretical point of view, for the development of the theory of sorption of polyfunctional compounds from multicomponent solutions. In general, the accumulation of experimental data on the retention of this kind of sorbates brings us closer to the solution of the problem of establishing the relationship between the characteristics of sorption, other physicochemical parameters, and the structure of molecules.
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