Synthesis and structural characterization of N-[4-(2-hydroxyethyl)-1,2,4- oxathiazinan-3-ylidene]-benzamide and its mercury(II) chloride adduct

Jorge Reinaldo Angulo Cornejo, Ketty Ayala-León, Gabriel García Herbosa, José V. Cuevas, Virginia Diez, Rainer Richter, Lothar Hennig, Lothar Beyer

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2 Scopus citations

Abstract

The synthesis of N-[4-(2-hydroxyethyl)-1,2,4-oxathiazinan-3-ylidene]- benzamide (2a) and N-[4-(2-hydroxyethyl)-1,2,4-oxathiazinan-3-ylidene]-2- fluorobenzamide (2b) by oxidation of the corresponding 1,1-bis(2-hydroxyethyl)- 3-aroylthioureas with potassium iodate in aqueous solution is reported. Variable temperature 1H NMR spectra of 2a prove that the heterocyclic 1,2,4-(O, S,N) six-membered ring is involved in a dynamic chair-boat conformational interconversion. Molecular mechanic calculations show that the chair conformation is more stable than the boat conformation by 3.0 kcal/mol. The synthesis of the adduct [(2a)·0.5 HgCl2] 3 as well as the X-ray structural characterization of 2a and 3 are also reported.

Original languageEnglish
Pages (from-to)945-950
Number of pages6
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume60
Issue number9
DOIs
StatePublished - Sep 2005
Externally publishedYes

Bibliographical note

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Keywords

  • Crystal Structure
  • Mercury(II) Chloride Adduct
  • NMR Data
  • Oxathiazinanes
  • Synthesis

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