A Database Study of the Bonding and Conformation of Bis-sulfonylamide/-imide Moieties

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Abstract

The bonding and conformational characteristics of bissulfonylamides and analogous imides are compared. Structures (44 altogether) containing R - SO2 -NQ - SO2 - R′ units were retrieved from the Cambridge Structural Database. They are either neutral (Q=H, alkyl or aryl groups, hereto atoms such as O and S) or charged (Q =e-) and bearing the functions R, R′=Me, Et or Ph, respectively. The principal conformations of the - SO2 - NQ - SO2 - bridge (open versus folded) are represented by sodium dibenzenesulfonamide (BSULFA) and dibenzenesulfonimide (NABSUF). In addition to the compounds possessing Q=alkyl or aryl functions, complexes with N-metal bonds could clearly be distinguished. The dominant forms of SVI - X (X=O, N C) bonds are characterized and correlated with the bond angles formed around the S atoms. The marked difference between the archetypes of the S - N bonds (i.e. nitrogen charged or neutral) indicated that the interdependence of the S -X bonds, i.e. the size and the shape of the SVI[O,O′,N,C] tetrahedra, are principally governed by the environment of the N atoms. The conformation symmetry and dissymmetry of the charged and neutral - SO2 - NQ - SO2 - moieties are described in terms of the internal rotations about the bonds in the R - S - N - S - R′ fragment.

Original languageEnglish
Pages (from-to)720-727
Number of pages8
JournalActa Crystallographica Section B: Structural Science
Volume52
Issue number4
DOIs
Publication statusPublished - Aug 1 1996

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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