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The influence of the type of halogen substituent and its position on the molecular conformation, intermolecular interactions and crystal packing for a series of 1-benzoyl-3-(halogenophenyl)thioureas
Abstract
By the reaction of benzoyl chloride, potassium isothiocyanate and the appropriate halogenoaniline, i.e. 2/3/4-(bromo/iodo)aniline, we have obtained five new 1-benzoyl-3-(halogenophenyl)thioureas, namely, 1-benzoyl-3-(2-bromophenyl)- thiourea and 1-benzoyl-3-(3-bromophenyl)thiourea, C14H11BrN2OS, and 1-benzoyl-3-(2-iodophenyl)thiourea, 1-benzoyl-3-(3-iodophenyl)thiourea and 1-benzoyl-3-(4-iodophenyl)thiourea, C14H11IN2OS. Structural and conformational features of the compounds have been analyzed using X-ray diffraction and theoretical calculations. The novel compounds were characterized by solid-state IR and 1H/13C NMR spectroscopy. The conformations and intermolecular interactions, such as hydrogen bonds, pi–pi and S(6)... pi stacking, and X...O (X = Br or I) , I...S and I...pi, have been examined and rationalized, together with four analogous compounds described previously in the literature. The set of nine compounds was chosen to examine how a change of the halogen atom and its position on the phenyl ring affects the molecular and crystal structures.
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- Copyright (2021 International Union of Crystallography)
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- Category:
- Articles
- Type:
- artykuły w czasopismach
- Published in:
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Acta Crystallographica Section C-Structural Chemistry
no. 77,
pages 11 - 19,
ISSN: 2053-2296 - Language:
- English
- Publication year:
- 2021
- Bibliographic description:
- Rosiak D., Okuniewski A., Chojnacki J.: The influence of the type of halogen substituent and its position on the molecular conformation, intermolecular interactions and crystal packing for a series of 1-benzoyl-3-(halogenophenyl)thioureas// Acta Crystallographica Section C-Structural Chemistry -Vol. 77,iss. 1 (2021), s.11-19
- DOI:
- Digital Object Identifier (open in new tab) 10.1107/s2053229620015594
- Verified by:
- Gdańsk University of Technology
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