Synthesis and Structural Characterization of N-[4-(2-Hydroxyethyl)-1,2,4-oxathiazinan-3-ylidene]-benzamide and its Mercury(II) Chloride Adduct

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

doi:10.1515/znb-2005-0906

Open Access Published by De Gruyter June 2, 2014

Synthesis and Structural Characterization of N-[4-(2-Hydroxyethyl)-1,2,4-oxathiazinan-3-ylidene]-benzamide and its Mercury(II) Chloride Adduct

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

From the journal Zeitschrift für Naturforschung B

https://doi.org/10.1515/znb-2005-0906

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) sixmembered 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.

Keywords: Oxathiazinanes; Mercury(II) Chloride Adduct; Synthesis; Crystal Structure; NMR Data

Received: 2005-6-16

Published Online: 2014-6-2

Published in Print: 2005-9-1

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Synthesis and Structural Characterization of N-[4-(2-Hydroxyethyl)-1,2,4-oxathiazinan-3-ylidene]-benzamide and its Mercury(II) Chloride Adduct

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