Substituent effect on the proton-related phenomena and chelation behavior of hydroxypicolinic compounds: a DFT investigation |
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Authors: | Nuttawisit Yasarawan Khajadpai Thipyapong Vithaya Ruangpornvisuti |
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Affiliation: | 1.Department of Chemistry, Faculty of Science,Burapha University,Chonburi,Thailand;2.Department of Chemistry, Faculty of Science,Chulalongkorn University,Bangkok,Thailand |
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Abstract: | Comparative study on kinetics and thermodynamics of proton-related reactions of hydroxypicolinic acids has been carried out using density functional theory associated with polarizable continuum model of solvation. Mechanisms for such reactions have been established. Both 3- and 4-hydroxypicolinic acid prefer zwitterionic forms to normal forms. For 6-hydroxypicolinic acid, keto forms are highly preferred. The pK a values and UV/Vis bands predicted for some picolinic compounds agree with the experiment. 5-Hydroxypicolinate shows the highest preference for complexation with copper(II) but 6-hydroxypolinate gives rise to the most stable complex. Kinetic stability of the trans-isomer relative to the cis-isomer of the complexes has been evaluated. UV/Vis spectral data predicted for some picolinate complexes are also in agreement with the previous experiment. |
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