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α-Ketoacid Intermolecular Hydrogen Bonding. Supramolecular Ribbons and Stacking in α-Pyrroleglyoxylic Acids

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Summary.

Rarely-seen carboxylic acid to ketone intermolecular hydrogen bonding is found in crystal structures of α-pyrroleglyoxylic acids. 3,4-Diethyl-1H-pyrrole-2-glyoxylic acid, prepared by saponfication of the reaction product between 3,4-diethylpyrrole and ethyl oxalyl chloride formed crystals that showed the uncommon carboxyl to ketone intermolecular hydrogen bonding, with the hydrogen-bonded α-pyrroleglyoxylic acids stacked neatly in layers. This α-ketoacid hydrogen-bonding pattern was repeated in (Z)-2,3,7,8-tetraethyl-10H-dipyrrin-1-one-9-glyoxylic acid, which also engaged in dipyrrinone-to-dipyrrinone intermolecular hydrogen bonding to form supramolecular ribbons in the crystal.

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Authors and Affiliations

  1. Department of Chemistry, University of Nevada, Reno, Nevada, USA

    Nicholas T. Salzameda & David A. Lightner

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  1. Nicholas T. Salzameda
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  2. David A. Lightner
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Correspondence to David A. Lightner.

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Salzameda, N., Lightner, D. α-Ketoacid Intermolecular Hydrogen Bonding. Supramolecular Ribbons and Stacking in α-Pyrroleglyoxylic Acids. Monatsh. Chem. 137, 1453–1462 (2006). https://doi.org/10.1007/s00706-006-0538-5

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  • DOI: https://doi.org/10.1007/s00706-006-0538-5

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