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

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	945-950
Number of pages	6
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	60
Issue number	9
DOIs	https://doi.org/10.1515/znb-2005-0906
State	Published - Sep 2005
Externally published	Yes

Bibliographical note

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

Keywords

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

Access to Document

10.1515/znb-2005-0906

Cite this

Angulo-Cornejo, J. R., Ayala-León, K., Herbosa, G. G., Cuevas, J. V., Diez, V., Richter, R., Hennig, L., & Beyer, L. (2005). Synthesis and structural characterization of N-[4-(2-hydroxyethyl)-1,2,4- oxathiazinan-3-ylidene]-benzamide and its mercury(II) chloride adduct. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 60(9), 945-950. https://doi.org/10.1515/znb-2005-0906

@article{7f01079e8b724b5f9e6694182f405291,

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

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.",

keywords = "Crystal Structure, Mercury(II) Chloride Adduct, NMR Data, Oxathiazinanes, Synthesis",

author = "Angulo-Cornejo, {Jorge R.} and Ketty Ayala-Le{\'o}n and Herbosa, {Gabriel Garc{\'i}a} and Cuevas, {Jos{\'e} V.} and Virginia Diez and Rainer Richter and Lothar Hennig and Lothar Beyer",

year = "2005",

month = sep,

doi = "10.1515/znb-2005-0906",

language = "Ingl{\'e}s",

volume = "60",

pages = "945--950",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

issn = "0932-0776",

publisher = "Walter de Gruyter GmbH",

number = "9",

}

Angulo-Cornejo, JR, Ayala-León, K, Herbosa, GG, Cuevas, JV, Diez, V, Richter, R, Hennig, L & Beyer, L 2005, 'Synthesis and structural characterization of N-[4-(2-hydroxyethyl)-1,2,4- oxathiazinan-3-ylidene]-benzamide and its mercury(II) chloride adduct', Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, vol. 60, no. 9, pp. 945-950. https://doi.org/10.1515/znb-2005-0906

Synthesis and structural characterization of N-[4-(2-hydroxyethyl)-1,2,4- oxathiazinan-3-ylidene]-benzamide and its mercury(II) chloride adduct. / Angulo-Cornejo, Jorge R.; Ayala-León, Ketty; Herbosa, Gabriel García et al.
In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 60, No. 9, 09.2005, p. 945-950.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and structural characterization of N-[4-(2-hydroxyethyl)-1,2,4- oxathiazinan-3-ylidene]-benzamide and its mercury(II) chloride adduct

AU - Angulo-Cornejo, Jorge R.

AU - Ayala-León, Ketty

AU - Herbosa, Gabriel García

AU - Cuevas, José V.

AU - Diez, Virginia

AU - Richter, Rainer

AU - Hennig, Lothar

AU - Beyer, Lothar

PY - 2005/9

Y1 - 2005/9

N2 - 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.

AB - 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.

KW - Crystal Structure

KW - Mercury(II) Chloride Adduct

KW - NMR Data

KW - Oxathiazinanes

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=27544433116&partnerID=8YFLogxK

U2 - 10.1515/znb-2005-0906

DO - 10.1515/znb-2005-0906

M3 - Artículo

AN - SCOPUS:27544433116

SN - 0932-0776

VL - 60

SP - 945

EP - 950

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 9

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this