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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...

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Autores principales: Gelbrich, Thomas, Lampl, Martin, Laus, Gerhard, Kahlenberg, Volker, Huppertz, Hubert, Schottenberger, Herwig
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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