The molecular structure of N,N '-disulfinyl-3,4,5,6-tetrafluoro-1,2-diaminobenzene: A computational and X-ray diffraction study

The molecular structure of N,N '-disulfinyl-3,4,5,6-tetrafluoro-1,2-diaminobenzene: A computational and X-ray diffraction study Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

Output data

Year: 2010, Volume: 978, Number: 1-3, Pages: 158-162 Pages count : DOI: 10.1016/j.molstruc.2010.01.070

Tags

N-Sulfinylaminobenzene; Configuration; Conformation; X-ray diffraction; Quantum chemical calculations

Authors

Makarov Arkady G. ² , Bagryanskaya Irina Yu. ² , Gatilov Yuri V. ² , Makarov Alexander Yu. ² , Tersago Karla , Van Alsenoy Christian ¹ , Blockhuys Frank ¹ , Zibarev Andrey V. ^2,3

Affiliations

1	(Данные Web of science) Univ Antwerp, Dept Chem, BE-2610 Antwerp, Belgium
2	(Данные Web of science) Russian Acad Sci, Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Dept Phys, Novosibirsk 630090, Russia

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 H center dot center dot center dot O hydrogen bonds, are also discussed. (C) 2010 Elsevier B.V. All rights reserved.

Makarov A.G. , Bagryanskaya I.Y. , Gatilov Y.V. , Makarov A.Y. , Tersago K. , Van Alsenoy C. , Blockhuys F. , Zibarev A.V.
The molecular structure of N,N '-disulfinyl-3,4,5,6-tetrafluoro-1,2-diaminobenzene: A computational and X-ray diffraction study
Journal of Molecular Structure. 2010. V.978. N1-3. P.158-162. DOI: 10.1016/j.molstruc.2010.01.070 WOS Scopus

Published print:

Aug 1, 2010

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