Intramolecular sulphur(II)-oxygen interaction in acyl chlorides: an X-ray study of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride

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

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6 Citations (Scopus)

Abstract

The molecular structures of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride have been determined by X-ray diffraction and compared with those of analogous methyl esters. No essential change in conformation and structural data occurs when o-COOMe is replaced by o-COCl. The sulphide/disulphide models preserve the skew/equatorial conformation with S(II)⋯O (carbonyl) distances of 2.721, 2.945/2.653 and 2.664 Å, and with θ(Car/SS⋯O) angles of 173.0, 77.4/171.8 and 174.0° characterizing the S(II)⋯O (carbonyl) type interaction with X = Car or S as the counter-atom. Intermolecular S(II)⋯Cl close contacts controlling the molecular structures in the crystal lattice were not observed.

Original languageEnglish
Pages (from-to)355-364
Number of pages10
JournalJournal of Molecular Structure
Volume198
Issue numberC
DOIs
Publication statusPublished - 1989

Fingerprint

Molecular Structure
Sulfur
Molecular structure
Conformations
Chlorides
molecular structure
Railroad cars
sulfur
chlorides
X-Rays
Oxygen
X rays
disulfides
Sulfides
oxygen
crystal lattices
X-Ray Diffraction
Crystal lattices
Disulfides
sulfides

ASJC Scopus subject areas

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

Cite this

@article{012a631b87124800bb8190ef1e0165f4,
title = "Intramolecular sulphur(II)-oxygen interaction in acyl chlorides: an X-ray study of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride",
abstract = "The molecular structures of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride have been determined by X-ray diffraction and compared with those of analogous methyl esters. No essential change in conformation and structural data occurs when o-COOMe is replaced by o-COCl. The sulphide/disulphide models preserve the skew/equatorial conformation with S(II)⋯O (carbonyl) distances of 2.721, 2.945/2.653 and 2.664 {\AA}, and with θ(Car/SS⋯O) angles of 173.0, 77.4/171.8 and 174.0° characterizing the S(II)⋯O (carbonyl) type interaction with X = Car or S as the counter-atom. Intermolecular S(II)⋯Cl close contacts controlling the molecular structures in the crystal lattice were not observed.",
author = "L. P{\'a}rk{\'a}ny{\'i} and A. K{\'a}lm{\'a}n and {\'A} Kucsman and I. Kapovits",
year = "1989",
doi = "10.1016/0022-2860(89)80049-3",
language = "English",
volume = "198",
pages = "355--364",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "C",

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TY - JOUR

T1 - Intramolecular sulphur(II)-oxygen interaction in acyl chlorides

T2 - an X-ray study of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride

AU - Párkányí, L.

AU - Kálmán, A.

AU - Kucsman, Á

AU - Kapovits, I.

PY - 1989

Y1 - 1989

N2 - The molecular structures of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride have been determined by X-ray diffraction and compared with those of analogous methyl esters. No essential change in conformation and structural data occurs when o-COOMe is replaced by o-COCl. The sulphide/disulphide models preserve the skew/equatorial conformation with S(II)⋯O (carbonyl) distances of 2.721, 2.945/2.653 and 2.664 Å, and with θ(Car/SS⋯O) angles of 173.0, 77.4/171.8 and 174.0° characterizing the S(II)⋯O (carbonyl) type interaction with X = Car or S as the counter-atom. Intermolecular S(II)⋯Cl close contacts controlling the molecular structures in the crystal lattice were not observed.

AB - The molecular structures of 2,2′-thiodibenzoyl chloride and 2,2′-dithiodibenzoyl chloride have been determined by X-ray diffraction and compared with those of analogous methyl esters. No essential change in conformation and structural data occurs when o-COOMe is replaced by o-COCl. The sulphide/disulphide models preserve the skew/equatorial conformation with S(II)⋯O (carbonyl) distances of 2.721, 2.945/2.653 and 2.664 Å, and with θ(Car/SS⋯O) angles of 173.0, 77.4/171.8 and 174.0° characterizing the S(II)⋯O (carbonyl) type interaction with X = Car or S as the counter-atom. Intermolecular S(II)⋯Cl close contacts controlling the molecular structures in the crystal lattice were not observed.

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U2 - 10.1016/0022-2860(89)80049-3

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JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

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