Salts of barbituric and 2-thiobarbituric acids with imidazole: polymorphism, supramolecular structure, thermal stability and water solubility

Salts of barbituric and 2-thiobarbituric acids with imidazole: polymorphism, supramolecular structure, thermal stability and water solubility Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2023, Volume: 47, Pages: 21790–21803 Pages count : DOI: 10.1039/d3nj04516a

Authors

Lakeev Alexander P. ^1,2 , Sukhikh Taisiya S. ³ , Kurzina Irina A. ¹ , Korotchenko Natalia M. ¹ , Nikitin Dmitriy S. ⁴

Affiliations

1	Faculty of Chemistry, National Research Tomsk State University, 36, Lenin Ave., Tomsk 634050, Russia
2	Goldberg Research Institute of Pharmacology and Regenerative Medicine, Tomsk National Research Medical Center, Russian Academy of Sciences, 3, Lenin Ave., Tomsk 634028, Russia
3	Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3, Acad. Lavrentiev Ave., Novosibirsk 630090, Russia
4	National Research Tomsk Polytechnic University, 30, Lenin Ave., Tomsk 634050, Russia

Barbituric acids are a useful tool for the construction of various supramolecular compounds with intriguing physicochemical properties. Also, barbiturates play a significant role in biology and medicine. The same is true for imidazole derivatives. Herein, three novel salts of barbituric (H2BA) and 2-thiobarbituric (H2TBA) acids with imidazole (Im), namely imidazolium barbiturate in two polymorphic modifications, HIm(HBA) (1) (pale yellow) and (2) (pale orange), and imidazolium 2-thiobarbiturate, HIm(HTBA) (3), were synthesized and characterized by CHNS elemental analysis, single-crystal and powder X-ray diffraction, FT-IR and UV-Vis spectroscopy techniques. Crystal structure analysis revealed that the compounds feature three different supramolecular architectures with the formula unit count (Z0) varying from 1 for 3 to 4 for 1, which is governed by an unusual geometry of hydrogen bonding motifs. Intermolecular interactions in crystals 1–3 were analyzed using 2D-fingerprint plots derived from the Hirshfeld surfaces. According to the TG-DSC analysis, compounds 1–3 were thermally stable up to B100 1C in air. The solubility studies (solubility product constants and solubility at a fixed pH value were determined) showed that salts 2 and 3 were more soluble in water than H2(T)BA. To the best of our knowledge, this is one of the first reports on the phenomenon of polymorphism among organic salts with barbiturate moieties. Thus, the present findings broaden our understanding of the supramolecular organization of barbiturates, complement the systematic studies of the correlation between their crystal structure and physicochemical properties and lay the foundation for the further development of novel materials based on imidazolium (2-thio)barbiturates.

Lakeev A.P. , Sukhikh T.S. , Kurzina I.A. , Korotchenko N.M. , Nikitin D.S.
Salts of barbituric and 2-thiobarbituric acids with imidazole: polymorphism, supramolecular structure, thermal stability and water solubility
New Journal of Chemistry. 2023. V.47. P.21790–21803. DOI: 10.1039/d3nj04516a WOS Scopus РИНЦ OpenAlex

Submitted:	Sep 27, 2023
Accepted:	Oct 30, 2023
Published online:	Nov 17, 2023
Published print:	Dec 5, 2023

Web of science:	WOS:001103972000001
Scopus:	2-s2.0-85178311027
Elibrary:	64540437
OpenAlex:	W4388768963

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