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Substituent effect on the proton-related phenomena and chelation behavior of hydroxypicolinic compounds: a DFT investigation

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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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Acknowledgments

N.Y. and K.T. are grateful to the Faculty of Science at Burapha University for partial financial support and laboratory facilities.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand

    Nuttawisit Yasarawan & Khajadpai Thipyapong

  2. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Vithaya Ruangpornvisuti

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  1. Nuttawisit Yasarawan
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  2. Khajadpai Thipyapong
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  3. Vithaya Ruangpornvisuti
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Correspondence to Nuttawisit Yasarawan.

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Yasarawan, N., Thipyapong, K. & Ruangpornvisuti, V. Substituent effect on the proton-related phenomena and chelation behavior of hydroxypicolinic compounds: a DFT investigation. Struct Chem 27, 505–524 (2016). https://doi.org/10.1007/s11224-015-0579-7

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