The structural analysis and modelling of ring substituent effect for the ortho-derivatives of 1-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides
| Autor: | Vladimír Lukeš, Martin Michalík, Peter Škorňa, Erik Klein |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Organic Chemistry Substituent 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Computational chemistry Amide Intramolecular force Molecule Moiety Conformational isomerism Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1144:473-481 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2017.05.069 |
| Popis: | The quantum chemical DFT study of 1-hydroxynaphthalene-2-carboxanilide ( A–H ) and 2-hydroxynaphthalene-1-carboxanilide ( B–H ) and their selected ortho -derivatives ( A–R, B–R ) is presented. The structural analysis showed that the energetically preferred conformation is stabilized via the intramolecular hydrogen bonds occurring between the C O⋯H–O1 of A–H molecule and C O⋯H–O2 groups of B–H molecule. The A–R derivatives are practically planar, while the B–R derivatives are slightly distorted due to the spatial repulsion of hydrogen atoms. The conformation analysis of molecules with deprotonated hydroxyl group supports the concept of existence of two conformer types with respect to the NH CO bridge orientation. Stabilization of the naphtholate moiety by a hydrogen bond to the amide NH group may allow the compound to cross the membrane to the extracellular space. The ortho substitution effect on the selected calculated properties was analyzed and the theoretical data were correlated with the substituent constants. For the B–R derivatives, the antitubercular activity concentrations were correlated and predicted by the calculated quantities. |
| Databáze: | OpenAIRE |
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