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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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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. |
format | Text |
id | pubmed-2968358 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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