Structure of aminonitrones and electronic effect of substituents on their acid-base properties


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Abstract

A series of para-substituted aromatic aminonitrones p-RC6H4C(NH2)=N+(Me)O (R = NMe2, H, Br, Cl, CF3) have been prepared. Acidity constants of the conjugate acids RC6H4C(NH2)N+(Me)OH at 25°C in a EtOH–H2O mixture (5: 95) have been determined by potentiometric titration. A linear correlation between log (kR/kH) and σpara values has been revealed, and a ρ298para) parameter has been determined as of 0.635.

About the authors

M. V. Il’in

St. Petersburg State University

Email: dmitriy.s.bolotin@gmail.com
Russian Federation, Universitetskaya nab. 7–9, St. Petersburg, 199034

D. S. Bolotin

St. Petersburg State University

Author for correspondence.
Email: dmitriy.s.bolotin@gmail.com
Russian Federation, Universitetskaya nab. 7–9, St. Petersburg, 199034

M. Ya. Demakova

St. Petersburg State University

Email: dmitriy.s.bolotin@gmail.com
Russian Federation, Universitetskaya nab. 7–9, St. Petersburg, 199034

M. S. Avdontseva

St. Petersburg State University

Email: dmitriy.s.bolotin@gmail.com
Russian Federation, Universitetskaya nab. 7–9, St. Petersburg, 199034


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