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4-Bromo-N-(diethyl­carbamothio­yl)­benzamide

The synthesis of the title compound, C(12)H(15)BrN(2)OS, involves the reaction of 4-bromo­benzoyl chloride with potassium thio­cyanate in dry acetone, followed by condensation of 4-bromo­benzoyl isothio­cyanate with diethyl­amine. The carbonyl and thio­carbonyl bond lengths indicate that these corre...

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Detalles Bibliográficos
Autores principales: Binzet, Gün, Flörke, Ulrich, Külcü, Nevzat, Arslan, Hakan
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968358/
https://www.ncbi.nlm.nih.gov/pubmed/21582014
http://dx.doi.org/10.1107/S1600536809003183
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author Binzet, Gün
Flörke, Ulrich
Külcü, Nevzat
Arslan, Hakan
author_facet Binzet, Gün
Flörke, Ulrich
Külcü, Nevzat
Arslan, Hakan
author_sort Binzet, Gün
collection PubMed
description The synthesis of the title compound, C(12)H(15)BrN(2)OS, involves the reaction of 4-bromo­benzoyl chloride with potassium thio­cyanate in dry acetone, followed by condensation of 4-bromo­benzoyl isothio­cyanate with diethyl­amine. The carbonyl and thio­carbonyl bond lengths indicate that these correspond to double bonds. The short C—N bond lengths reveal the effects of resonance in this part of the mol­ecule. The conformation of the mol­ecule with respect to the thio­carbonyl and carbonyl units is twisted, with torsion angles of −5.7 (3) and 87.2 (2)°. The N atom of the diethyl­amine group is sp (2)-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and − anti­periplanar conformations with angles of −179.89 and 179.92°. In the crystal structure, the mol­ecules form infinite chains via an inter­molecular N—H⋯O inter­action.
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spelling pubmed-29683582010-12-30 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide Binzet, Gün Flörke, Ulrich Külcü, Nevzat Arslan, Hakan Acta Crystallogr Sect E Struct Rep Online Organic Papers The synthesis of the title compound, C(12)H(15)BrN(2)OS, involves the reaction of 4-bromo­benzoyl chloride with potassium thio­cyanate in dry acetone, followed by condensation of 4-bromo­benzoyl isothio­cyanate with diethyl­amine. The carbonyl and thio­carbonyl bond lengths indicate that these correspond to double bonds. The short C—N bond lengths reveal the effects of resonance in this part of the mol­ecule. The conformation of the mol­ecule with respect to the thio­carbonyl and carbonyl units is twisted, with torsion angles of −5.7 (3) and 87.2 (2)°. The N atom of the diethyl­amine group is sp (2)-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and − anti­periplanar conformations with angles of −179.89 and 179.92°. In the crystal structure, the mol­ecules form infinite chains via an inter­molecular N—H⋯O inter­action. International Union of Crystallography 2009-01-31 /pmc/articles/PMC2968358/ /pubmed/21582014 http://dx.doi.org/10.1107/S1600536809003183 Text en © Binzet et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Binzet, Gün
Flörke, Ulrich
Külcü, Nevzat
Arslan, Hakan
4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title_full 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title_fullStr 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title_full_unstemmed 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title_short 4-Bromo-N-(diethyl­carbamothio­yl)­benzamide
title_sort 4-bromo-n-(diethyl­carbamothio­yl)­benzamide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968358/
https://www.ncbi.nlm.nih.gov/pubmed/21582014
http://dx.doi.org/10.1107/S1600536809003183
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