The molecular structures of divinyl sulfide and divinyl sulfoxide in the gas phase from electron diffraction

Béla Rozsondai, Zsolt E. Horváth

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The molecular geometries and conformations of divinyl sulfide (DVS), (CH2=CH)2S, and divinyl sulfoxide (DVSO), (CH 2=CH)2SO, have been determined by gas-phase electron diffraction and vibrational analysis. The C=C bonds tend to eclipse other bonds or a sulfur lone pair in the free molecules. The only conformer found in the vapours of DVS at room temperature has no symmetry and is characterized by dihedral angles C-S-C=C of 32(9)° and -148(7)°; both CH2 groups lie on the same side of the C-S-C plane. This form is very similar to the prevailing form of divinyl ether.8 DVSO is a mixture of conformers. The form present in 78(17)% at 82 °C has C-S-C=C of 121(4)° and -121(4)° and C, symmetry; both C=C bonds eclipse the S=O bonds. Intramolecular O ⋯ H(C) interactions of about 2.5 Å seem to stabilize existing conformers of DVSO. Important parameters are (rg with estimated total errors), for DVS: S-C 1.758(4), C=C 1.342(3), C-H 1.092(3), (C·H)mean (within a CH2=CH group) 2.108(6) Å, C-S-C 101.8(21)°, S-C=C 123.7(6)°; for DVSO: S=O 1.477(3), S-C 1.785(4), C=C 1.330(3), C-H 1.091(5), (C·H)mean 2.141(10) Å, C-S=O 107.5(14)°, C-S-C 99.2(18)°, S-C=C 118.5(8)°. Bond lengths do not indicate effects of conjugation in these molecules.

Original languageEnglish
Pages (from-to)1175-1180
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number6
DOIs
Publication statusPublished - Jan 1 1993
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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