Carboxylic acid to amide hydrogen bonding. 10-Oxo-semirubins |
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Authors: | Nicholas T Salzameda David A Lightner |
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Institution: | a Department of Chemistry, University of Nevada, Reno, NV 89557-0020, United States b Department of Chemistry, University of West Florida, Pensacola, FL 32514, United States |
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Abstract: | Using their amide (and pyrrole) groups, dipyrrinones act as hydrogen bonding receptors for carboxylic acids, as found in a large number of 10-oxo-semirubins (1-6). The latter can be synthesized readily by Friedel-Crafts coupling of 9-H dipyrrinones with half-ester acid chlorides or diacid dichlorides of α,ω-dicarboxylic acids, ranging from C2 to C10. With ω-oxo-alkanoic acid chains of C5 or ≥C5, intramolecular hydrogen bonding is observed. With acid chains <C5 hydrogen bonding is not observed. Uncharacteristically (for dipyrrinones), 10-oxo-dipyrrinone acids (1-6) and their corresponding esters (1e-6e) remain monomeric in hydrogen bond promoting solvents. |
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Keywords: | Dipyrrinone Hydrogen bonds Nuclear Overhauser effect |
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