Abstract
Crystal structure of a series of 1-alkylimidazole-4,5-dicarboxylic acids has been determined. It is shown that an increase in the length of the alkyl group leads to drastic changes in the crystal and molecular structures. 1-Methyl and 1-ethylimidazole-4,5-dicarboxylic acid crystallize in zwitterionic form, but 1-propyl- and 1-butylimidazole-4,5-dicarboxylic acid crystallize as rare equimolar mixture of neutral and zwitterionic tautomeric forms. The observed changes in the crystal and molecular structures are apparently associated with the steric factor, which determines both the packing method and the tautomeric composition of the unit cell.
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Research ethics: Not applicable.
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Author contributions: All the authors have accepted responsibility for the entire content of submitted manuscript and approved its submission.
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Competing interests: The authors declare no conflict of interest regarding this article.
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Research funding: Research was carried out under support of the Ministry of Education and Science of Russian Federation in the sphere of research activity (project no. FGWG-2022-0004 2022-2025).
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Data availability: The raw data can be obtained on request from the corresponding author.
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Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/zkri-2023-0022).
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