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A thermodynamic study on the complexation between riboflavin and a diaminotriazine derivative mediated by triple hydrogen bonds at water/oil interfaces

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Abstract

The changes in Gibbs free energy (ΔG int), enthalpy (ΔH int) and entropy (TΔS int) upon complexation between riboflavin (RF) and N,N-dioctadecyl-[1,3,5]triazine-2,4,6-triamine (DTT), mediated by triple hydrogen bonds at water/carbon tetrachloride, trichloroethylene and chloroform interfaces, were determined via temperature-controlled interfacial tension measurements. It was shown that hydrogen bonding interactions between RF and DTT were best characterized by large and negative ΔH int values, unlike those predicted from either the polarity in each phase or the arithmetic average of the polarities in the two phases. Furthermore, the ΔH int values became more positive as the dielectric constant of the oil phase was increased. These results strongly indicate that ΔH int is governed by the dielectric properties of the oil phase. Adsorption of RF, DTT and the RF-DTT complex at the water/oil interface gave rise to restrictions on the translational and rotational motions of these species, as demonstrated by the ΔS int values observed, which is another characteristic of interfacial complexation. The thermodynamic parameters evaluated in the present study revealed the characteristic complexation behavior that occurs at a water/oil interface, as mediated by hydrogen bonding.

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Acknowledgements

The authors are grateful for a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of the Japanese Government, which supported the research (No. 15750061 and No. 13129201 (Priority Research Area on “Nano-Chemistry at Liquid-Liquid Interfaces”).

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Authors and Affiliations

  1. Division of Chemistry, Graduate School of Science, Hokkaido University, Kita-ku, Sapporo, 060-0810, Japan

    Shoji Ishizaka, Yoshiaki Nishijima & Noboru Kitamura

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  1. Shoji Ishizaka
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  2. Yoshiaki Nishijima
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  3. Noboru Kitamura
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Correspondence to Noboru Kitamura.

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Ishizaka, S., Nishijima, Y. & Kitamura, N. A thermodynamic study on the complexation between riboflavin and a diaminotriazine derivative mediated by triple hydrogen bonds at water/oil interfaces. Anal Bioanal Chem 386, 749–758 (2006). https://doi.org/10.1007/s00216-006-0573-4

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  • DOI: https://doi.org/10.1007/s00216-006-0573-4

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