Influence of the inductive effect on the protolytic properties of some aliphatic amino acids

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Resumo

The protolytic propertiesof a number of aliphatic amino acids, viz. serine (Ser),cysteine (Cys), glycine (Gly), alanine (Ala), valine (Val), leucine (Leu),and isoleucine (Ile) in aqueous solutions atT = 298.2 K andI = 0.1 mol/L NaNO3are studiedby pH monitoring. Using the calculated ionization constants of aminoacids and the equation allowing one to quantify the inductiveeffect in the aliphatic series (the Taft equation), the substituentconstantσ*is calculated, with its values showing a positivecorrelation with the ionization constants of amino acids (рKi) (R2= 0.9561 andR2= 0.8542). Theresults show that the acidity of the studied amino acidsdecreases as follows Cys > Ser > Gly > Gly> Leu > Ala > Ile > Val. The acid-baseproperties of amino acids are found to change depending onthe inductive effect (the radical constantσ*). Among thestudied amino acids, Cys exhibits the highest acidity and isconsidered to be the weakest base.

Sobre autores

A. Samadov

Tajik National University

Email: s.rasul@mail.ru
Dushanbe, 734025 Tajikistan

Dzh. Khakimov

Tajik National University

Email: s.rasul@mail.ru
Dushanbe, 734025 Tajikistan

A. Stepnova

Peoples’ Friendship University of Russia

Email: s.rasul@mail.ru
Moscow, 117198 Russia

E. Faizullozoda

Tajik National University

Email: s.rasul@mail.ru
Dushanbe, 734025 Tajikistan

A. Kuzin

Moscow Pedagogical State University

Autor responsável pela correspondência
Email: s.rasul@mail.ru
Moscow, 129164 Russia

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