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Synthesis, hydrogen bond interactions and crystal structure elucidation of some stable 2H-imidazolium salts

Synthesis, hydrogen bond interactions and crystal structure elucidation of some stable... AbstractReaction of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (1) with phthalimide, quinazolinedione, thiophenole and 4-pyridinethiole led to the formation of the hydrogen-bonded salts, imidazolium phthalimide (2), imidazolium quinazolinedione (3), imidazolium thiophenolate (4) and imidazolium 4-pyridinethiolate (5), respectively, in good yield. In crystals of 2, the anion is linked to the imidazolium cation by a C–H···O hydrogen bond, while in 3 and 5 C–H···N hydrogen bonds are observed. In 4, the imidazolium ion is linked to the anion by C–H···S hydrogen bonds. In compounds 2, 3 and 5, the interionic hydrogen bonds are close to linearity, while the interionic hydrogen bond angle in 4 is 148.5(9)°. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Synthesis, hydrogen bond interactions and crystal structure elucidation of some stable 2H-imidazolium salts

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Publisher
de Gruyter
Copyright
© 2021 Walter de Gruyter GmbH, Berlin/Boston
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2021-0132
Publisher site
See Article on Publisher Site

Abstract

AbstractReaction of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (1) with phthalimide, quinazolinedione, thiophenole and 4-pyridinethiole led to the formation of the hydrogen-bonded salts, imidazolium phthalimide (2), imidazolium quinazolinedione (3), imidazolium thiophenolate (4) and imidazolium 4-pyridinethiolate (5), respectively, in good yield. In crystals of 2, the anion is linked to the imidazolium cation by a C–H···O hydrogen bond, while in 3 and 5 C–H···N hydrogen bonds are observed. In 4, the imidazolium ion is linked to the anion by C–H···S hydrogen bonds. In compounds 2, 3 and 5, the interionic hydrogen bonds are close to linearity, while the interionic hydrogen bond angle in 4 is 148.5(9)°.

Journal

Zeitschrift für Naturforschung Bde Gruyter

Published: Jan 27, 2022

Keywords: crystal structures; heterocycles; hydrogen bonds; imidazolium salts

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