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, G. Argay, M. Czugler, V. Fülöp, A. Kálmán, T. Koritsánsky, L. Párkányí

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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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sulfoxide
zwitterions
Molecular Structure
Molecular structure
molecular structure
Salts
Ions
salts
Bond length
Sulfides
Sulfur
X-Ray Diffraction
Methanol
Conformations
sulfides
Railroad cars
sulfur
methyl alcohol
intervals
X ray diffraction

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

@article{c295cc6e203e4e20a27a3243544eb079,
title = "Spirosulfuranes with different heteroatoms in axial positions A comparison of NS(IV)O and NS+(IV){triple dot, diagonal SW-NE}O systems",
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 {\AA} and from 2.13 to 2.225 {\AA}, respectively (1.69 and 2.60 {\AA} 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 {\AA}). 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.",
author = "D. Szab{\'o} and I. Kapovits and {\'A} Kucsman and P. Huszthy and G. Argay and M. Czugler and V. F{\"u}l{\"o}p and A. K{\'a}lm{\'a}n and T. Korits{\'a}nsky and L. P{\'a}rk{\'a}ny{\'i}",
year = "1993",
month = "12",
day = "3",
doi = "10.1016/0022-2860(93)87004-S",
language = "English",
volume = "300",
pages = "23--46",
journal = "Journal of Molecular Structure",
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TY - JOUR

T1 - Spirosulfuranes with different heteroatoms in axial positions A comparison of NS(IV)O and NS+(IV){triple dot, diagonal SW-NE}O systems

AU - Szabó, D.

AU - Kapovits, I.

AU - Kucsman, Á

AU - Huszthy, P.

AU - Argay, G.

AU - Czugler, M.

AU - Fülöp, V.

AU - Kálmán, A.

AU - Koritsánsky, T.

AU - Párkányí, L.

PY - 1993/12/3

Y1 - 1993/12/3

N2 - 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.

AB - 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.

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