Title
The molecular structure of N,N′-disulfinyl-3,4,5,6-tetrafluoro-1,2-diaminobenzene: A computational and X-ray diffraction study
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Amsterdam ,
Subject
Physics
Chemistry
Source (journal)
Journal of molecular structure. - Amsterdam
Volume/pages
978(2010) :1/3 , p. 158-162
ISSN
0022-2860
ISI
000281083300025
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
According to the results of quantum chemical calculations at various levels of theory, an isolated molecule of the title compound prefers a non-planar Z,Z configuration, which is very similar to the configuration observed in the crystal. This is in contrast to its previously studied hydrocarbon analogue which features a planar Z,Z configuration, both in the crystal and as a calculated structure. Thus, the gas-phase molecular structures of these flexible compounds are resistant to the numerous intermolecular interactions in the solid state. The results obtained for the different molecular configurations and conformations of these compounds are in line with the qualitative bonding model suggested earlier for the isoelectronic [RNSN]− anions, taking into account of the anomeric interactions and the electron-acceptor strength of R. A number of additional factors operating on the molecular conformations of the title compound and its hydrocarbon analogue, such as the van der Waals volume of the ortho-substituents X (X = H,F) and improper HO hydrogen bonds, are also discussed.
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