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Solvatochromism, prototropism and complexation of para-aminobenzoic acid

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Abstract

Effect of solvents, buffer solutions of different pH and β-cyclodextrin (β-CD) on the absorption and fluorescence spectra of p-aminobenzoic acid (pABA) have been investigated. The inclusion complex of pABA with β-CD is investigated by UV-visible, fluorimetry, semiempirical quantum calculations (AM1), 1H NMR and Scanning Electron Microscope (SEM). The thermodynamic parameters (ΔH, ΔG and ΔS) of the inclusion process are also determined. The experimental results indicated that the inclusion processes is an exothermic and spontaneous. The large Stokes shift emission in solvents with pABA are correlated with different solvent polarity scales. The increase in the excited dipole moment values suggest that pABA molecule is more polar in the S1 state. Solvent and β-CD studies indicates intramolecular charge transfer in pABA is less than ortho and meta isomers. Acidity constants for different prototropic equilibria of pABA in the S0 and S1 states are calculated. β-Cyclodextrin studies shows that pABA forms a 1:1 inclusion complex with β-CD. A mechanism is proposed to explain the inclusion process.

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Acknowledgements

One of the author (N.R) is thankful to the Department of Science and Technology, New Delhi, for the financial support to the Project under Fast Track Proposal –Young Scientist Scheme No. SR/FTP/CS−14/2005.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, Tamil Nadu, India

    T. Stalin & N. Rajendiran

  2. Department of Physics, Annamalai University, Annamalainagar, 608 002, Tamil Nadu, India

    B. Shanthi & P. Vasantha Rani

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  1. T. Stalin
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  2. B. Shanthi
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  3. P. Vasantha Rani
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  4. N. Rajendiran
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Correspondence to N. Rajendiran.

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Stalin, T., Shanthi, B., Rani, P.V. et al. Solvatochromism, prototropism and complexation of para-aminobenzoic acid. J Incl Phenom Macrocycl Chem 55, 21–29 (2006). https://doi.org/10.1007/s10847-005-9013-x

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  • DOI: https://doi.org/10.1007/s10847-005-9013-x

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