Dimethyl 5-acetyl-1-hy-droxy-4-methyl-1H-pyrrole-2,3-di-carboxyl-ate, an oxidation-resistant N-hy-droxy-pyrrole

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

doi:10.1107/S1600536813034466

Dimethyl 5-acetyl-1-hy-droxy-4-methyl-1H-pyrrole-2,3-di-carboxyl-ate, an oxidation-resistant N-hy-droxy-pyrrole

Acta Crystallogr Sect E Struct Rep Online. 2014 Jan 4;70(Pt 2):o110-1. doi: 10.1107/S1600536813034466. eCollection 2014 Feb 1.

Authors

Gerald M Rosen¹, Sukumaran Muralidharan², Peter Y Zavalij³, Joseph P Y Kao⁴

Affiliations

¹ Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, Maryland 21201, USA.
² Center for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA.
³ Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
⁴ Center for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA ; Department of Physiology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA.

Abstract

The title compound, C11H13NO6, exhibits an intra-molecular 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.

Grants and funding

R01 GM056481/GM/NIGMS NIH HHS/United States