Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole

The title compound, C(11)H(13)NO(6), exhibits an intra­molecular O–H⋯O=C hydrogen bond between the N-hydroxyl H atom and carbonyl O atom of the neighboring acetyl group. This finding contradicts a previously published model in which the hydrogen bond was postulated to occur with the neighboring carb...

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Autores principales: Rosen, Gerald M., Muralidharan, Sukumaran, Zavalij, Peter Y., Kao, Joseph P. Y.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998280/
https://www.ncbi.nlm.nih.gov/pubmed/24764841
http://dx.doi.org/10.1107/S1600536813034466
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author Rosen, Gerald M.
Muralidharan, Sukumaran
Zavalij, Peter Y.
Kao, Joseph P. Y.
author_facet Rosen, Gerald M.
Muralidharan, Sukumaran
Zavalij, Peter Y.
Kao, Joseph P. Y.
author_sort Rosen, Gerald M.
collection PubMed
description The title compound, C(11)H(13)NO(6), exhibits an intra­molecular O–H⋯O=C hydrogen bond between the N-hydroxyl H atom and carbonyl O atom of the neighboring acetyl group. This finding contradicts a previously published model in which the hydrogen bond was postulated to occur with the neighboring carbomethoxy group. This relatively strong hydrogen bond [O—H⋯O: D = 2.5583 (11) Å and θ = 152°] may underlie the resistance of the title compound to oxidation into the corresponding nitroxide.
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spelling pubmed-39982802014-04-24 Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole Rosen, Gerald M. Muralidharan, Sukumaran Zavalij, Peter Y. Kao, Joseph P. Y. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(13)NO(6), exhibits an intra­molecular O–H⋯O=C hydrogen bond between the N-hydroxyl H atom and carbonyl O atom of the neighboring acetyl group. This finding contradicts a previously published model in which the hydrogen bond was postulated to occur with the neighboring carbomethoxy group. This relatively strong hydrogen bond [O—H⋯O: D = 2.5583 (11) Å and θ = 152°] may underlie the resistance of the title compound to oxidation into the corresponding nitroxide. International Union of Crystallography 2014-01-04 /pmc/articles/PMC3998280/ /pubmed/24764841 http://dx.doi.org/10.1107/S1600536813034466 Text en © Rosen et al. 2014 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
Rosen, Gerald M.
Muralidharan, Sukumaran
Zavalij, Peter Y.
Kao, Joseph P. Y.
Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title_full Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title_fullStr Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title_full_unstemmed Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title_short Dimethyl 5-acetyl-1-hy­droxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­droxy­pyrrole
title_sort dimethyl 5-acetyl-1-hy­droxy-4-methyl-1h-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant n-hy­droxy­pyrrole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998280/
https://www.ncbi.nlm.nih.gov/pubmed/24764841
http://dx.doi.org/10.1107/S1600536813034466
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