Reactivity of Inorganic α-Nucleophiles in Acyl Transfer in Aqueous and Micellar Media. IV. Peroxyhydrolysis of Acylcontaining Compounds in Organized Microheterogenic Systems

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Resumo

Micellar effects in perhydrolysis and base catalyzed hydrolysis of 4-nitrophenyl esters of phosphoric, phosphonic and toluolsulphonic acids in organized microheterogeneous systems based on dicationic (Gemini surfactant, GS – AlkIm+–(CH2)3–Im+Alk ∙ 2Br–, Alk = C12H25 or C14H29) and monocationic (AlkIm+CH3 ∙ Br– , Alk = C12H25 or C14H29) surfactants have been analyzed. The effect of concentration of reagents is the main factor responsible for micellar catalysis. Hydroperoxide α-effect described as second order rate constants ratio for perhydrolysis and base catalyzed hydrolysis remains in organized media, and, depending on surfactant/substrate nature, may amount to ~ 100.

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Sobre autores

Maria Turovskaya

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
ORCID ID: 0000-0003-4129-0270
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Irina Belousova

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
ORCID ID: 0000-0003-1534-5506
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Nina Razumova

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Tatiana Gaidash

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Tatiana Prokopyeva

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
ORCID ID: 0000-0003-0867-7449
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Alla Kotenko

Litvinenko Institute of Physical Organic and Coal Chemistry

Autor responsável pela correspondência
Email: alla.a.kotenko@yandex.ru
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

Vasily Mikhailov

Litvinenko Institute of Physical Organic and Coal Chemistry

Email: alla.a.kotenko@yandex.ru
ORCID ID: 0000-0002-4184-1805
Rússia, 70, Rosa Luxemburg St., Donetsk, 283048

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2. Fig. 1. Brønsted dependence for the NPDEP and NPDEPN reactions with inorganic α-nucleophiles; water; 25°C.

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3. Scheme 1

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4. Scheme 2

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5. Scheme 3

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6. Fig. 2. Dependence of k2,each values (k2,each = kobserved / [HOO–]) on GS 1b concentration for peroxyhydrolysis of acyl-containing substrates; pH 11.0; water; 25°C.

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7. Fig. 3. Dependence of k2 values on GS concentration for peroxyhydrolysis: (a) NPDEPN (compound 2a – o; compound 2b – ♦); (b) NPDEP (compound GS 1a – o; compound GS 1b – ♦); pH 11.0; water; 25°C.

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8. Fig. 4. Dependence of k2 values on GS concentration with varying methylene spacer length (m) for NPOTos peroxyhydrolysis; pH 11.0; water; 25°C.

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