Spirosulfuranes with different heteroatoms in axial positions A comparison of NS(IV)O and NS+(IV){triple dot, diagonal SW-NE}O systems

D. Szabó, I. Kapovits, Á Kucsman, P. Huszthy, Gy Argay, M. Czugler, V. Fülöp, A. Kálmán, T. Koritsánsky, L. Párkányi

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Abstract

Three novel spirosulfuranes with N and O heteroatoms in axial positions and with five- and six-membered spirorings (4-6), as well as the molecular complex of the dipolar ion 7 with methanol, have been prepared and their molecular structures determined by X-ray diffraction. The molecular structures of the spirosulfuranes 4-6 show slightly distorted geometries, while that of the dipolar ion 7 is considerably distorted about the central sulfur. The axial interatomic distances for SN and SO in 4-6 range from 1.71 to 1.74 Å and from 2.13 to 2.225 Å, respectively (1.69 and 2.60 Å for 7). The axial NSO and the equatorial CarSCar angles lie in the intervals 174-179° and 104-105°, respectively, for the spirosulfuranes 4-6 (157 and 104° for 7). The SCr bond lengths in all of the compounds investigated are similar to those given for typical S(IV)Car bonds (1.76-1.82 Å). A comparison is also presented between the structural parameters of the spirosulfurances 4-6 and those of the cyclic sulfonium salts 1a-3 and of the molecular complex 7 with analogous structures to the spirosulfuranes studied. The conformations for all of the model compounds as well as for the sulfoxide 8 and sulfide 9 related to the spirosulfuranes and sulfonium salts investigated are also discussed.

Original languageEnglish
Pages (from-to)23-46
Number of pages24
JournalJournal of Molecular Structure
Volume300
Issue numberC
DOIs
Publication statusPublished - Dec 3 1993

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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