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Theoretical study on the intramolecular hydrogen bond in chloro-substituted N,N-dimethylaminomethylphenols. I. Structural effects |
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| Authors: | A Koll V Parasuk W Parasuk A Karpfen P Wolschann |
| Institution: | a Department of Chemistry, University of Wroclaw, ul. Joliot-Curie 14, Wroclaw PL-50-383, Poland b Faculty of Science, Department of Chemistry, University of Chulalongkorn, Bangkok 10330, Thailand c Faculty of Science, Department of Chemistry, University of Kasetsart, Bangkok 10900, Thailand d Institute of Theoretical Chemistry and Structural Biology, University of Vienna, Währinger Straße 17, Vienna A-1090, Austria |
| Abstract: | Ab initio and density functional calculations are applied to study the influence of an increasing number of chlorine substituents on the properties of the intramolecular hydrogen bond in substituted Mannich bases. It is shown, that not only the acidity of the proton donor, which depends on the number of chlorine atoms at the aromatic ring, but also steric interactions modify the geometry of the hydrogen bond. Specific interactions of O–Cl H–O hydrogen-bonding in some derivatives are estimated by calculations on related chlorophenols. |
| Keywords: | Ab initio calculations DFT methods Mannich bases Intramolecular hydrogen bonding Substituent effects |
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