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

Gerald M. Rosen; Sukumaran Muralidharan; Peter Y. Zavalij; Joseph P. Y. Kao

doi:10.1107/S1600536813034466

Acta Crystallographica Section E (Feb 2014)

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

Gerald M. Rosen,
Sukumaran Muralidharan,
Peter Y. Zavalij,
Joseph P. Y. Kao

Affiliations

Gerald M. Rosen: Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, Maryland 21201, USA
Sukumaran Muralidharan: Center for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA
Peter Y. Zavalij: Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA
Joseph P. Y. Kao: Center for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA

DOI: https://doi.org/10.1107/S1600536813034466
Journal volume & issue: Vol. 70, no. 2
pp. o110 – o111

Abstract

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The title compound, C11H13NO6, 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.

Published in Acta Crystallographica Section E

ISSN: 1600-5368 (Online)
Publisher: International Union of Crystallography
Country of publisher: United Kingdom
LCC subjects: Science: Chemistry: Crystallography
Website: https://journals.iucr.org/e/

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