Intramolecular S···S and S···O close contacts in 1,8-bis(phenylsulfanyl)naphthalene derivatives of different sulfur valence state: An X-ray study

Péter Nagy, Dénes Szabó, István Kapovits, Árpád Kucsman, Gyula Argay, Alajos Kálmán

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30 Citations (Scopus)

Abstract

Four peri-substituted naphthalene derivatives, 1,8-bis(phenylsulfanyl)naphthalene (1), 1,8-bis[(2-methoxycarbonylphenyl)sulfanyl]naphthalene (2), bis[(2-methoxycarbonyl-phenyl)-sulfinyl]naphthalene (3) and bis[(2-methoxycarbonylphenyl)sulfonyl]naphthalene (4) with different valence states of sulfur were prepared and their molecular structures determined by X-ray diffraction. Data were collected on CAD-4 diffractometers with monochromated MoKα and CuKα radiations. Naphthalene ring torsions, aromatic ring orientations, S···S and S···O close contacts were analyzed and the controlling factors established. In both halves of the molecules, the naphthyl and phenyl rings assume axial-equatorial positions in bis-sulfides 1 and 2, and twist-axial positions in bis-sulfoxide 3 and bis-sulfone 4. The S···S distance was found to be 3.01, 3.18; 3.01 and 3.53 Å, for 1, 2, 3 and 4, respectively. The equatorial S-phenyl rings in 2 and the steric crowd in 4 are unfavorable factors for S···S contacts. As expected, S(II)···O and S(IV)···O close contacts are formed in the equatorial and axial S-phenyl rings of 2 and 3, respectively, with 2.72, 2.73 and 2.77, 2.83 Å distances. Steric repulsion in bis-sulfone 4 is moderated by two C(ar)-S(VI)···O(sulfonyl) type close contacts (2.89 and 3.02 Å), which join the two halves of the molecule.

Original languageEnglish
Pages (from-to)61-76
Number of pages16
JournalJournal of Molecular Structure
Volume606
Issue number1-3
DOIs
Publication statusPublished - Mar 27 2002

Keywords

  • Conformation
  • Crystal structures
  • S···S and S···O nonbonded interaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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