Be̅rziņš, A;
Semjonova, A;
Actiņš, A;
Salvalaglio, M;
(2021)
Speciation of Substituted Benzoic Acids in Solution: Evaluation of Spectroscopic and Computational Methods for the Identification of Associates and Their Role in Crystallization.
Crystal Growth and Design
, 21
(9)
pp. 4823-4836.
10.1021/acs.cgd.0c01605.
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Abstract
Self-association of four benzoic acid derivatives 2-chloro-4-nitrobenzoic acid, 2-methyl-4-nitrobenzoic acid, 3-hydroxybenzoic acid, and 2,6-dimethoxybenzoic acid in solution was investigated using spectroscopic measurements (Fourier transform infrared and 1H and 13C NMR spectroscopy) and molecular simulation methods. Based on the formation of hydrogen bonds, solvents can be divided into two groups: apolar solvents or solvents with a low hydrogen bond acceptor propensity, in which the benzoic acid derivatives form hydrogen-bonded dimers, and solvents with hydrogen bond acceptor propensity β > 0.3, interacting with the carboxylic group of benzoic acid, thus screening its interaction in the formation of self-associates. The formation propensity and structure of self-associates stabilized by weak interactions, such as π···π stacking and CH3···π interactions, however, are determined by the substituents in the benzene ring. Despite all the studied compounds being polymorphic, in none of the cases, an unequivocal structural link between self-associates present in the solution and the crystal form was observed.
| Type: | Article |
|---|---|
| Title: | Speciation of Substituted Benzoic Acids in Solution: Evaluation of Spectroscopic and Computational Methods for the Identification of Associates and Their Role in Crystallization |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/acs.cgd.0c01605 |
| Publisher version: | https://doi.org/10.1021/acs.cgd.0c01605 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Chemical Engineering |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10135021 |
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