DOI: https://doi.org/10.24959/ophcj.19.968

The reactivity of propyl esters of 2-(benzoylamino)(1-R-2-oxoindoline-3-ylidene) acetic acids

O. M. Svechnikova, S. V. Kolisnyk, O. F. Vynnyk, O. O. Altukhov, T. A. Kostina

Abstract


Aim. To study the reactivity of esters of 2-(benzoylamino)(1-R-2-oxoindoline-3-ylidene) acetic acids.
Results and discussion. The reaction rate constants of alkaline hydrolysis of esters of 2-(benzoylamino) (1-R-2-oxoindoline-3-ylidene) acetic acids depend on the structure and the length of the hydrocarbon chain at the heterocyclic nitrogen atom. Introduction of hydrocarbon radicals to the structure of the heterocycle slows down the reaction, while the chain extension accelerates it. The effect of the electronic nature of the substituents on the reactivity of propyl esters was quantitatively assessed by Hammett equation. The data obtained suggest that the values of the reaction parameter ρ are positive in the temperature range studied; it is additionally confirmed by the ВАС2 mechanism of this reaction.
Experimental part. The concentration of NaOH in the solution was determined by potentiometric titration on an EV-74 ionomer using the standard aqueous HCl solution. The reaction kinetics was performed in triplicates, the experiments contained 6-8 measurements (the depth of the change was not less than 80 %). The accuracy of the results obtained was assessed by the methods of mathematical statistics of small samples with statistical significance of 0.95.
Conclusions. The reaction kinetics of alkaline hydrolysis of biologically active propyl esters of 2-(benzoylamino)(1-R-2-oxoindoline-3-ylidene) acetic acids has been studied in a wide temperature range; its ВАС2 mechanism has been proven with formation of a highly symmetrical intermediate. The effect of the substituents at the heterocyclic nitrogen atom on the numerous kinetic and activation parameters of the reaction has been analyzed; isokineticity and synchronicity of the reaction have been proven using independent tests.

 


Keywords


reactivity; alkaline hydrolysis; derivatives of 2-(benzoylamino)(1-R-2-oxoindoline-3-ylidene) acetic acids

References


Zamorskii, І. І., Bukataru, Y. S., Lenga, E. L., Kolisnyk, S. V., Altukhov, O. O. (2016). Screening of derivatives of 2–(benzoylamino)(1–R–2–oxoindolin–3–ylidene)acetic acid under the conditions of acute hypobaric hypoxia. Vìsnik Farmacìï, 1 (85), 67–70. https://doi.org/10.24959/nphj.16.2104

Kolesnik, S. V., Altukhov, A. A., Akhmedov, E. Yu., Torianik, E. L. (2014). Azerbaidzhanskii farmatcevticheskii i farmakoterapevticheskii zhurnal, 1, 14–18.

Gaidukevich, A. N., Svechnikova, E. N., Kazakov, G. P., Kostina, T. A. (1986). Reactivity of Derivatives of Phenilanthranilic Acid. I. Reaction kinetics of Alkaline Hydrolysis of 4’–Derivatives of β–Dimethylaminoethyl Esters of 4–Chloro–N–phenylanthranilic acids in Binary Dioxane–Water Solvent. Organic Reactivity, 4 (84), 440–449.

Kolisnyk S. V., Svechnikova O. M., Vinnyk О. F., Kolisnyk О. V., Altukhov O. O. (2018). The reactivity of ethyl esters of 2–(benzoylamino)(1–R–2–oxoindoline–3–ylidene) acetic acids. Vìsnik Farmacìï, 2 (94), 3–7. https://doi.org/10.24959/nphj.18.2209

Streltsov, O. A., Melnychuk, D. O., Snitynskyi, V. V., Fedkevych, Ye. V. (2002). Fizychna ta koloidna khimiia. Lviv : Liha–Pres, 92–94.

Bolotov, V. V., Sviechnikova, О. M., Kolisnyk, S. V. (2004). Analitychna khimiia. Kharkiv : NUPh, Oryhinal, 427–433.


GOST Style Citations


1.Screening of derivatives of 2–(benzoylamino)(1–R–2–oxoindolin–3–ylidene)acetic acid under the conditions of acute hypobaric hypoxia / I. I. Zamorskii, Yu. S. Bukataru, E. L. Lenga et al. // Вісник фармації. – 2016. – № 1 (85). – С. 67–70. https://doi.org/10.24959/nphj.16.2104

 

2. Синтез, свойства и биологическая активность амидированных производных 2–(бензоиламино)(2–оксоиндолин–3–илиден)уксусной кислоты / С. В. Колесник, А. А. Алтухов, Э. Ю. Ахмедов, Э. Л. Торяник // Азербайджанский фармацевтический и фармакотерапевтический журн. – 2014. – № 1. – С. 14–18.

 

3. Reactivity of Derivatives of Phenilanthranilic Acid. I. Reaction kinetics of Alkaline Hydrolysis of 4’–Derivatives of β–Dimethylaminoethyl Esters of 4–Chloro–N–phenylanthranilic acids in Binary Dioxane–Water Solvent / A. N. Gaidukevich, E. N. Svechnikova, G. P. Kazakov, T. A. Kostina // Organic Reactivity. – 1986. – Vol. 4, Issue 84. – P. 440–449.


4. The reactivity of ethyl esters of 2–(benzoylamino)(1–R–2–oxoindoline–3–ylidene) acetic acids / S. V. Kolisnyk, O. M. Svechnikova, О. F. Vinnyk et al. // Вісник фармації. – 2018. – № 2 (94). – С. 3–7. https://doi.org/10.24959/nphj.18.2209

 

 5. Фізична та колоїдна хімія / О. А. Стрельцов, Д. О. Мельничук, В. В. Снітинський та ін. – Л. : Ліга–Прес, 2002. – С. 92–94.

 

6. Аналітична хімія / В. В. Болотов, О. М. Свєчнікова, С. В. Колісник та ін. – Х. : НФаУ; Оригінал, 2004. – C. 427–433.





Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Abbreviated key title: J. Org. Pharm. Chem.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)