Intramolecular Hydrogen Bond Strength and pK a Determination of N,N‘-Disubstituted Imidazole-4,5-dicarboxamides

N,N ‘-Disubstituted imidazole-4,5-dicarboxamides (I45DCs) form an intramolecular hydrogen bond worth an estimated 14 ± 1 kcal/mol, as measured with a model structure in DMSO-d 6 at 3 mM, thereby predisposing the molecular conformation to a folded rather than extended form. The I45DCs also show evide...

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Published inOrganic letters Vol. 7; no. 1; pp. 135 - 138
Main Authors Rush, Jeremy R, Sandstrom, Stacey L, Yang, Jianqing, Davis, Rebecca, Prakash, Om, Baures, Paul W
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.01.2005
Subjects
Hydrogen Bonding
Imidazoles - chemistry
Magnetic Resonance Spectroscopy
Thermodynamics
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Summary:N,N ‘-Disubstituted imidazole-4,5-dicarboxamides (I45DCs) form an intramolecular hydrogen bond worth an estimated 14 ± 1 kcal/mol, as measured with a model structure in DMSO-d 6 at 3 mM, thereby predisposing the molecular conformation to a folded rather than extended form. The I45DCs also show evidence of aggregation in both CDCl3 (>1 mM) and DMSO-d 6 (>10 mM) solutions. These compounds are uncharacteristically weak bases in comparison with imidazoles bearing similar electron-withdrawing groups.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol047812a