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Supramolecular Organization in Salts of Riluzole with Dihydroxybenzoic Acids—The Key Role of the Mutual Arrangement of OH Groupsстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Voronin Alexander P., Surov Artem O., Churakov Andrei V., Vener Mikhail V.
- Журнал: Pharmaceutics
- Том: 15
- Номер: 3
- Год издания: 2023
- Издательство: MDPI
- Местоположение издательства: Basel, Switzerland
- Первая страница: 878
- DOI: 10.3390/pharmaceutics15030878
- Аннотация: Intermolecular interactions, in particular hydrogen bonds, play a key role in crystal engineering. The ability to form hydrogen bonds of various types and strengths causes competitionbetween supramolecular synthons in pharmaceutical multicomponent crystals. In this work, we investigate the influence of positional isomerism on the packing arrangements and the networkof hydrogen bonds in multicomponent crystals of the drug riluzole with hydroxyl derivatives ofsalicylic acid. The supramolecular organization of the riluzole salt containing 2,6-dihydroxybenzoicacid differs from that of the solid forms with 2,4- and 2,5-dihydroxybenzoic acids. Because thesecond OH group is not at position 6 in the latter crystals, intermolecular charge-assisted hydrogenbonds are formed. According to periodic DFT calculations, the enthalpy of these H-bonds exceeds 30 kJ/mol. The positional isomerism appears to have little effect on the enthalpy of the primary supramolecular synthon (65–70 kJ/mol), but it does result in the formation of a two-dimensional network of hydrogen bonds and an increase in the overall lattice energy. According to the results of the present study, 2,6-dihydroxybenzoic acid can be treated as a promising counterion for the design of pharmaceutical multicomponent crystals.
- Добавил в систему: Венер Михаил Владимирович