Dimethyl 5-acetyl-1-hy-droxy-4-methyl-1H-pyrrole-2,3-di-carboxyl-ate, an oxidation-resistant N-hy-droxy-pyrrole.
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.
Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, Maryland 21201, USA.
Gerald M
GM
Rosen
Center for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA.
Sukumaran
S
Muralidharan
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
Peter Y
PY
Zavalij
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.
Joseph P Y
JP
Kao