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Protonation of γ‐Butyrolactone and γ‐Butyrolactam

Abstract: γ‐Butyrolactone and γ‐butyrolactam were reacted in the superacidic systems XF/MF(5) (X=H, D; M=As, Sb). Salts of the monoprotonated species of γ‐butyrolactone were obtained in terms of [(CH(2))(3)OCOH](+)[AsF(6)](−), [(CH(2))(3)OCOH](+)[SbF(6)](−) and [(CH(2))(3)OCOD](+)[AsF(6)](−) and the...

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Autores principales: Beck, Stefanie, Feller, Michael, Spies, Laura, Dietrich, Kai J., Jessen, Christoph, Stierstorfer, Karin, Kornath, Andreas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7780814/
https://www.ncbi.nlm.nih.gov/pubmed/33332769
http://dx.doi.org/10.1002/open.202000220
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author Beck, Stefanie
Feller, Michael
Spies, Laura
Dietrich, Kai J.
Jessen, Christoph
Stierstorfer, Karin
Kornath, Andreas J.
author_facet Beck, Stefanie
Feller, Michael
Spies, Laura
Dietrich, Kai J.
Jessen, Christoph
Stierstorfer, Karin
Kornath, Andreas J.
author_sort Beck, Stefanie
collection PubMed
description Abstract: γ‐Butyrolactone and γ‐butyrolactam were reacted in the superacidic systems XF/MF(5) (X=H, D; M=As, Sb). Salts of the monoprotonated species of γ‐butyrolactone were obtained in terms of [(CH(2))(3)OCOH](+)[AsF(6)](−), [(CH(2))(3)OCOH](+)[SbF(6)](−) and [(CH(2))(3)OCOD](+)[AsF(6)](−) and the analogous lactam salts in terms of [(CH(2))(3)NHCOH](+)[AsF(6)](−), [(CH(2))(3)NHCOH](+)[SbF(6)](−) and [(CH(2))(3)NDCOD](+)[AsF(6)](−). The salts were characterized by low temperature Raman and infrared spectroscopy and for both protonated hexafluoridoarsenates, [(CH(2))(3)OCOH](+)[AsF(6)](−) and [(CH(2))(3)NHCOH](+)[AsF(6)](−), single‐crystal X‐ray structure analyses were conducted. In addition to the experimental results, quantum chemical calculations were performed on the B3LYP/aug‐cc‐pVTZ level of theory. As in both crystal structures C⋅⋅⋅F contacts were observed, the nature of these contacts is discussed with Mapped Electrostatic Potential as a rate of strength.
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spelling pubmed-77808142021-01-08 Protonation of γ‐Butyrolactone and γ‐Butyrolactam Beck, Stefanie Feller, Michael Spies, Laura Dietrich, Kai J. Jessen, Christoph Stierstorfer, Karin Kornath, Andreas J. ChemistryOpen Full Papers Abstract: γ‐Butyrolactone and γ‐butyrolactam were reacted in the superacidic systems XF/MF(5) (X=H, D; M=As, Sb). Salts of the monoprotonated species of γ‐butyrolactone were obtained in terms of [(CH(2))(3)OCOH](+)[AsF(6)](−), [(CH(2))(3)OCOH](+)[SbF(6)](−) and [(CH(2))(3)OCOD](+)[AsF(6)](−) and the analogous lactam salts in terms of [(CH(2))(3)NHCOH](+)[AsF(6)](−), [(CH(2))(3)NHCOH](+)[SbF(6)](−) and [(CH(2))(3)NDCOD](+)[AsF(6)](−). The salts were characterized by low temperature Raman and infrared spectroscopy and for both protonated hexafluoridoarsenates, [(CH(2))(3)OCOH](+)[AsF(6)](−) and [(CH(2))(3)NHCOH](+)[AsF(6)](−), single‐crystal X‐ray structure analyses were conducted. In addition to the experimental results, quantum chemical calculations were performed on the B3LYP/aug‐cc‐pVTZ level of theory. As in both crystal structures C⋅⋅⋅F contacts were observed, the nature of these contacts is discussed with Mapped Electrostatic Potential as a rate of strength. John Wiley and Sons Inc. 2020-12-17 /pmc/articles/PMC7780814/ /pubmed/33332769 http://dx.doi.org/10.1002/open.202000220 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Beck, Stefanie
Feller, Michael
Spies, Laura
Dietrich, Kai J.
Jessen, Christoph
Stierstorfer, Karin
Kornath, Andreas J.
Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title_full Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title_fullStr Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title_full_unstemmed Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title_short Protonation of γ‐Butyrolactone and γ‐Butyrolactam
title_sort protonation of γ‐butyrolactone and γ‐butyrolactam
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7780814/
https://www.ncbi.nlm.nih.gov/pubmed/33332769
http://dx.doi.org/10.1002/open.202000220
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