The reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids
Keywords:reactivity, N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids
The study of the reactivity of substances allows optimizing the conditions of their synthesis and creating mathematical models of the “structure-biological activity” relationship that enable to carry out the targeted search of compounds with a specified high level of the biological action.
Aim. To study the reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids.
Materials and methods. The reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids was studied in reversible conditions on the model of acid-base equilibria by the method of potentiometric titration.
Results and discussion. The ionization constants of 9 propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids indicate that these compounds are weak acids. Elongation of the methylene fragments in the amino acid groups of molecules decreases their acidity. In contrast to the length of the methylene fragments their branching and the presence of the substituents do not affect acidity of the esters studied. In the framework of the principle of linearity of free energies the effect of the length of the methylene chain in the amino acid fragment of the molecules of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids was quantitatively assessed by Hammett equation.
Conclusions. It has been found that propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids have the functions of weak monobasic acids. Elongation of the polymethylene chain weakens ionization. The low sensitivity of the reaction center to elongation of the methylene chain has been identified.
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