Spectrophotometric study of the protonation processes of some indole derivatives in sulfuric acid

• Main Authors: Andonovski Blagoja S., Stojković Goran M.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 1999-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: 3-methylindole; d-tryptophan; 3-formylindole; 3-acetylindole; indolyl-2-carboxylic acid; protonation; dissociation constants; solvent parameter; hammett acidity function method; excess acidity method
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/1999/0352-51399912775A.pdf

The protonation of 3-methylindole, D-tryptophan, 3-formylindole, 3-acetylindole and indolyl-2-carboxylic acid in sulfuric acid media was studied by UV spectroscopy. The measurement of the absorbance at four selected wavelengths enabled the calculation of the corresponding molar absorptivities. The results were used to calculate the pKa value of the protonated form of the indole derivatives by the Hammett Method. The Hammett postulate (the slope of the plot log [c(BH+)/c(B)]vs. H should be equal to 1) was tested. The dissociation constants and solvent parameter m* were also obtained by applying the Excess Acidity Method. The position of the additional protons in the protonated compounds is discussed.