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Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings

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Abstract

1-[2′-(N-methylcarbamoyl)phenyl]-3H-2,1-naphto-(1,8-d,e)-oxathiin-1-ium chloride (2), 1-[2′-(N-methylcarbamoyl)-phenyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (3), 1-[8′-(N-methylcarbamoyl)naphtyl]-2-methyl-3-oxo-3H-1, 2-naphto-(1,8-d,e)-thiazin-1-ium chloride (4) and 1-(8′-carboxylatonaphtyl)-2-methyl-3-oxo-3H-1,2-naphto-(1,8-d,e)-thiazin-1-ium dipolar ion (5) cyclic sulfonium salts were prepared and their chemical properties investigated (spirosulfurane-formation, hydrolysis). The molecular structures obtained from x-ray diffraction can be described with a considerably distorted trigonal bipyramidal arrangement of the ligands about the sulfonium center, with O/N—S ... O=apical angles of 173.9, 164.9, 156.6, and 159.0°, as well as with S—O/N apical bond lengths of 1.648, 1.671, 1.664, and 1.682 Å. The structures exhibit relatively short S ... O close contacts with interatomic distances of 2.253, 2.448, 2.795, and 2.619 Å.

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Correspondence to István Kapovits or Alajos Kálmán.

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Szabó, D., Kapovits, I., Kucsman, Á. et al. Cyclic sulfonium salts with S ... O interactions 2. Molecular structures with six-membered rings. Struct Chem 2, 529–535 (1991). https://doi.org/10.1007/BF00672886

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Keywords

  • Chloride
  • Hydrolysis
  • Sulfonium
  • Phenyl
  • Molecular Structure