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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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. |
format | Online Article Text |
id | pubmed-7780814 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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