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Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates
Two salts were prepared by methylation of the respective imidazoline-2-thione at the sulfur atom, using Meerwein’s salt (trimethyloxonium tetrafluoridoborate) in CH(2)Cl(2). 1,3-Dimethoxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (1), C(6)H(11)N(2)O(2)S(+)·BF(4) (−), displays a syn...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7133041/ https://www.ncbi.nlm.nih.gov/pubmed/32280502 http://dx.doi.org/10.1107/S2056989020003643 |
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author | Gelbrich, Thomas Lampl, Martin Laus, Gerhard Kahlenberg, Volker Huppertz, Hubert Schottenberger, Herwig |
author_facet | Gelbrich, Thomas Lampl, Martin Laus, Gerhard Kahlenberg, Volker Huppertz, Hubert Schottenberger, Herwig |
author_sort | Gelbrich, Thomas |
collection | PubMed |
description | Two salts were prepared by methylation of the respective imidazoline-2-thione at the sulfur atom, using Meerwein’s salt (trimethyloxonium tetrafluoridoborate) in CH(2)Cl(2). 1,3-Dimethoxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (1), C(6)H(11)N(2)O(2)S(+)·BF(4) (−), displays a syn conformation of its two methoxy groups relative to each other whereas the two benzyloxy groups present in 1,3-dibenzyloxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (2), C(18)H(19)N(2)O(2)S(+)·BF(4) (−), adopt an anti conformation. In the molecules of 1 and 2, the methylsulfanyl group is rotated out of the plane of the respective heterocyclic ring. In both crystal structures, intermolecular interactions are dominated by C—H⋯F—B contacts, leading to three-dimensional networks. The tetrafluoridoborate counter-ion of 2 is disordered over three orientations (occupancy ratio 0.42:0.34:0.24), which are related by rotation about one of the B—F bonds. |
format | Online Article Text |
id | pubmed-7133041 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-71330412020-04-10 Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates Gelbrich, Thomas Lampl, Martin Laus, Gerhard Kahlenberg, Volker Huppertz, Hubert Schottenberger, Herwig Acta Crystallogr E Crystallogr Commun Research Communications Two salts were prepared by methylation of the respective imidazoline-2-thione at the sulfur atom, using Meerwein’s salt (trimethyloxonium tetrafluoridoborate) in CH(2)Cl(2). 1,3-Dimethoxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (1), C(6)H(11)N(2)O(2)S(+)·BF(4) (−), displays a syn conformation of its two methoxy groups relative to each other whereas the two benzyloxy groups present in 1,3-dibenzyloxy-2-(methylsulfanyl)imidazolium tetrafluoridoborate (2), C(18)H(19)N(2)O(2)S(+)·BF(4) (−), adopt an anti conformation. In the molecules of 1 and 2, the methylsulfanyl group is rotated out of the plane of the respective heterocyclic ring. In both crystal structures, intermolecular interactions are dominated by C—H⋯F—B contacts, leading to three-dimensional networks. The tetrafluoridoborate counter-ion of 2 is disordered over three orientations (occupancy ratio 0.42:0.34:0.24), which are related by rotation about one of the B—F bonds. International Union of Crystallography 2020-03-17 /pmc/articles/PMC7133041/ /pubmed/32280502 http://dx.doi.org/10.1107/S2056989020003643 Text en © Gelbrich et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Gelbrich, Thomas Lampl, Martin Laus, Gerhard Kahlenberg, Volker Huppertz, Hubert Schottenberger, Herwig Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title | Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title_full | Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title_fullStr | Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title_full_unstemmed | Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title_short | Synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
title_sort | synthesis and crystal structures of two 1,3-di(alkyloxy)-2-(methylsulfanyl)imidazolium tetrafluoridoborates |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7133041/ https://www.ncbi.nlm.nih.gov/pubmed/32280502 http://dx.doi.org/10.1107/S2056989020003643 |
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