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

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 ? = 152°] may underlie the resistance of the title compound to oxidation into the corresponding nitroxide.

SUBMITTER: Rosen GM 

PROVIDER: S-EPMC3998280 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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

Rosen Gerald M GM   Muralidharan Sukumaran S   Zavalij Peter Y PY   Kao Joseph P Y JP  

Acta crystallographica. Section E, Structure reports online 20140104 Pt 2

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. ...[more]

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