Intramolecular sulphur-oxygen interaction in organosulphur compounds with different sulphur valence state: an X-ray study of methyl-2-nitrobenzene-sulphenate, -sulphinate, -sulphonate and 2-nitrobenzenesulphenyl chloride

Á Kucsman, I. Kapovits, M. Czugler, L. Párkányí, A. Kálmán

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Abstract

Molecular structures of methyl-2-nitrobenzenesulphenate, methyl-2-nitrobenzenesulphinate, methyl-2-nitrobenzenesulphonate and 2-nitrobenzenesulphenyl chloride have been determined by X-ray diffraction. The remarkably short S⋯O (nitro) distances (2.458, 2.743, 2.956 and 2.379/2.408 Å) found in the almost linear XS⋯O sequences are controlled characteristically by both the valence state of sulphur and the electronegativity of the X counter-atom (X = OMe, O, OMe and Cl, respectively). The structure of the sulphonate is compared with that of the analogous sulphonyl chloride and conformations around the S(VI)Car bonds are discussed. In the crystal lattice of 2-nitrobenzenesulphenyl chloride, intermolecular S⋯Cl close contacts of two different types (3.447 and 3.452 Å) were observed. The differences in the geometries of adjacent molecules may be associated with these interactions.

Original languageEnglish
Pages (from-to)339-353
Number of pages15
JournalJournal of Molecular Structure
Volume198
Issue numberC
DOIs
Publication statusPublished - 1989

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Electronegativity
Nitrobenzene
nitrobenzenes
Chemical bonds
sulfonates
Sulfur
Crystal lattices
Molecular structure
Conformations
Chlorides
Railroad cars
sulfur
chlorides
X-Rays
Oxygen
valence
X ray diffraction
X rays
Atoms
Molecules

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

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title = "Intramolecular sulphur-oxygen interaction in organosulphur compounds with different sulphur valence state: an X-ray study of methyl-2-nitrobenzene-sulphenate, -sulphinate, -sulphonate and 2-nitrobenzenesulphenyl chloride",
abstract = "Molecular structures of methyl-2-nitrobenzenesulphenate, methyl-2-nitrobenzenesulphinate, methyl-2-nitrobenzenesulphonate and 2-nitrobenzenesulphenyl chloride have been determined by X-ray diffraction. The remarkably short S⋯O (nitro) distances (2.458, 2.743, 2.956 and 2.379/2.408 {\AA}) found in the almost linear XS⋯O sequences are controlled characteristically by both the valence state of sulphur and the electronegativity of the X counter-atom (X = OMe, O, OMe and Cl, respectively). The structure of the sulphonate is compared with that of the analogous sulphonyl chloride and conformations around the S(VI)Car bonds are discussed. In the crystal lattice of 2-nitrobenzenesulphenyl chloride, intermolecular S⋯Cl close contacts of two different types (3.447 and 3.452 {\AA}) were observed. The differences in the geometries of adjacent molecules may be associated with these interactions.",
author = "{\'A} Kucsman and I. Kapovits and M. Czugler and L. P{\'a}rk{\'a}ny{\'i} and A. K{\'a}lm{\'a}n",
year = "1989",
doi = "10.1016/0022-2860(89)80048-1",
language = "English",
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pages = "339--353",
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TY - JOUR

T1 - Intramolecular sulphur-oxygen interaction in organosulphur compounds with different sulphur valence state

T2 - an X-ray study of methyl-2-nitrobenzene-sulphenate, -sulphinate, -sulphonate and 2-nitrobenzenesulphenyl chloride

AU - Kucsman, Á

AU - Kapovits, I.

AU - Czugler, M.

AU - Párkányí, L.

AU - Kálmán, A.

PY - 1989

Y1 - 1989

N2 - Molecular structures of methyl-2-nitrobenzenesulphenate, methyl-2-nitrobenzenesulphinate, methyl-2-nitrobenzenesulphonate and 2-nitrobenzenesulphenyl chloride have been determined by X-ray diffraction. The remarkably short S⋯O (nitro) distances (2.458, 2.743, 2.956 and 2.379/2.408 Å) found in the almost linear XS⋯O sequences are controlled characteristically by both the valence state of sulphur and the electronegativity of the X counter-atom (X = OMe, O, OMe and Cl, respectively). The structure of the sulphonate is compared with that of the analogous sulphonyl chloride and conformations around the S(VI)Car bonds are discussed. In the crystal lattice of 2-nitrobenzenesulphenyl chloride, intermolecular S⋯Cl close contacts of two different types (3.447 and 3.452 Å) were observed. The differences in the geometries of adjacent molecules may be associated with these interactions.

AB - Molecular structures of methyl-2-nitrobenzenesulphenate, methyl-2-nitrobenzenesulphinate, methyl-2-nitrobenzenesulphonate and 2-nitrobenzenesulphenyl chloride have been determined by X-ray diffraction. The remarkably short S⋯O (nitro) distances (2.458, 2.743, 2.956 and 2.379/2.408 Å) found in the almost linear XS⋯O sequences are controlled characteristically by both the valence state of sulphur and the electronegativity of the X counter-atom (X = OMe, O, OMe and Cl, respectively). The structure of the sulphonate is compared with that of the analogous sulphonyl chloride and conformations around the S(VI)Car bonds are discussed. In the crystal lattice of 2-nitrobenzenesulphenyl chloride, intermolecular S⋯Cl close contacts of two different types (3.447 and 3.452 Å) were observed. The differences in the geometries of adjacent molecules may be associated with these interactions.

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