2,2-Dimethyl-5-nitroso-1,3-dioxan-5-yl benzoate, 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate and 5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate

Acta Crystallogr C. 2007 Jun;63(Pt 6):o365-8. doi: 10.1107/S0108270107021804. Epub 2007 May 31.

Abstract

The crystal structures of 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl benzoate, C(13)H(15)NO(5), (I), 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate, C(13)H(14)ClNO(5), (II), and 5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate, C(11)H(11)NO(5), (III), have been determined in order to gain insight into the conformational preference of alpha-benzoyloxynitroso. Unfavourable 1,3-diaxial interactions force (I) and (II) to crystallize in the 2,5 twist-boat conformation, whereas compound (III), lacking this destabilizing interaction, crystallizes in the chair conformation.

MeSH terms

  • Benzoates / chemistry*
  • Chlorobenzoates / chemistry*
  • Crystallography, X-Ray
  • Dioxanes / chemistry*
  • Molecular Conformation

Substances

  • 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate
  • 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl benzoate
  • 5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate
  • Benzoates
  • Chlorobenzoates
  • Dioxanes