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Spectral Characteristics of Sulfa Drugs: Effect of Solvents, pH and β-Cyclodextrin

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Abstract

The absorption and fluorescence spectra of sulfamethoxazole (SMO), sulfisoxazole (SFO), sulfathiazole (STO) and sulfanilamide (SAM) in different solvents, pH and β-cyclodextrin (β-CD) have been analyzed. The inclusion complexes of the above sulfa drugs with β-CD were investigated by UV-visible spectroscopy, fluorometry, DFT, SEM, FT-IR and 1H NMR. The solvent study indicates that the position of the substituent (oxazole or thiazole group) in the SAM molecule (R–SO2–NH-group) is not the key factor to change the absorption and emission behavior of these sulpha drug molecules. In aqueous solution, a single fluorescence band (340 nm) was observed whereas in solutions of β-CD dual emission (430 nm) was noticed in sulpha drug compounds. Formation of the inclusion complex in SMO, SFO and STO should result dual emission which is due to a Twisted Intramolecular Charge Transfer band (TICT). The β-CD study indicates that (i) sulpha drugs form 1:1 inclusion complexes with β-CD and (ii) the red shift and the presence of TICT in the β-CD medium confirms heterocyclic ring encapsulated in the β-CD cavity with the aniline ring present on the out side of the β-CD cavity.

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  1. Department of Chemistry, Annamalai University, Annamalai nagar, 608 002, Tamilnadu, India

    A. Antony Muthu Prabhu, G. Venkatesh & N. Rajendiran

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  1. A. Antony Muthu Prabhu
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  2. G. Venkatesh
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  3. N. Rajendiran
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Muthu Prabhu, A.A., Venkatesh, G. & Rajendiran, N. Spectral Characteristics of Sulfa Drugs: Effect of Solvents, pH and β-Cyclodextrin. J Solution Chem 39, 1061–1086 (2010). https://doi.org/10.1007/s10953-010-9559-0

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