Synthesis and piezoelectric properties of N-phthaloylglutamic acid derivatives


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Abstract

The (S,S)- and (R,R)-enantiomers of dimethyl 2,4-diphthalimidoglutarate were synthesized by nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloyl-glutamate upon treatment with potassium phthalimide, followed by separation. The crystal structure of the obtained compounds was studied by X-ray diffraction. Crystals of enantiomerically pure dimethyl 4-hydroxy- and 4-phthalimido-N-phthaloylglutamates were found to possess a noticeable piezoelectric activity.

About the authors

V. O. Ustinova

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

A. Yu. Vigorov

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

D. A. Gruzdev

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

A. S. Nuraeva

Institute of Natural Sciences and Mathematics, Ural Federal University

Email: gruzdev-da@ios.uran.ru
Russian Federation, 19 ul. Mira, Ekaterinburg, 620002

I. A. Nizova

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

E. N. Chulakov

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

L. Sh. Sadretdinova

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

P. A. Slepukhin

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Institute of Chemical Engineering, Ural Federal University

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990; 19 ul. Mira, Ekaterinburg, 620002

P. S. Zelenovsky

Institute of Natural Sciences and Mathematics, Ural Federal University

Email: gruzdev-da@ios.uran.ru
Russian Federation, 19 ul. Mira, Ekaterinburg, 620002

V. Ya. Shur

Institute of Natural Sciences and Mathematics, Ural Federal University

Email: gruzdev-da@ios.uran.ru
Russian Federation, 19 ul. Mira, Ekaterinburg, 620002

V. P. Krasnov

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gruzdev-da@ios.uran.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620990

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