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Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K
The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971979/ https://www.ncbi.nlm.nih.gov/pubmed/21578764 http://dx.doi.org/10.1107/S1600536809042512 |
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author | Sledz, Pawel Minor, Thomas Chruszcz, Maksymilian |
author_facet | Sledz, Pawel Minor, Thomas Chruszcz, Maksymilian |
author_sort | Sledz, Pawel |
collection | PubMed |
description | The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not previously reported [Gao, Yin, Yang, & Xue (2004). Acta Cryst. E60, o1328–o1329]. The change of protonation state of the nitrogen atom significantly affects the intermolecular interactions in the HEPES crystal. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds and ionic interactions, as the title compound in solid state is a zwitterion. HEPES molecules pack in layers that are held together by ionic and weak interactions, while a hydrogen-bonded network connects the layers. |
format | Text |
id | pubmed-2971979 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29719792010-12-30 Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K Sledz, Pawel Minor, Thomas Chruszcz, Maksymilian Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not previously reported [Gao, Yin, Yang, & Xue (2004). Acta Cryst. E60, o1328–o1329]. The change of protonation state of the nitrogen atom significantly affects the intermolecular interactions in the HEPES crystal. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds and ionic interactions, as the title compound in solid state is a zwitterion. HEPES molecules pack in layers that are held together by ionic and weak interactions, while a hydrogen-bonded network connects the layers. International Union of Crystallography 2009-11-07 /pmc/articles/PMC2971979/ /pubmed/21578764 http://dx.doi.org/10.1107/S1600536809042512 Text en © Sledz 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 Sledz, Pawel Minor, Thomas Chruszcz, Maksymilian Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title | Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title_full | Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title_fullStr | Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title_full_unstemmed | Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title_short | Redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 K |
title_sort | redetermination of 2-[4-(2-hydroxyethyl)piperazin-1-ium-1-yl]ethanesulfonate at 100 k |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971979/ https://www.ncbi.nlm.nih.gov/pubmed/21578764 http://dx.doi.org/10.1107/S1600536809042512 |
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