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The reactivity of benzoates in mixtures of water and aprotic solvents
Croatica Chemica Acta, 85 (2012), 4; 585-594. https://doi.org/10.5562/cca2179
Matić, Mirela; Denegri, Bernard; Kronja, Olga

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Matić, M., Denegri, B. i Kronja, O. (2012). The reactivity of benzoates in mixtures of water and aprotic solvents. Croatica Chemica Acta, 85. (4), 585-594. doi: 10.5562/cca2179

Matić, Mirela, et al. "The reactivity of benzoates in mixtures of water and aprotic solvents." Croatica Chemica Acta, vol. 85, br. 4, 2012, str. 585-594. https://doi.org/10.5562/cca2179

Matić, Mirela, Bernard Denegri i Olga Kronja. "The reactivity of benzoates in mixtures of water and aprotic solvents." Croatica Chemica Acta 85, br. 4 (2012): 585-594. https://doi.org/10.5562/cca2179

Matić, M., Denegri, B. i Kronja, O. (2012) 'The reactivity of benzoates in mixtures of water and aprotic solvents', Croatica Chemica Acta, 85(4), str. 585-594. doi: 10.5562/cca2179

Matić M, Denegri B, Kronja O. The reactivity of benzoates in mixtures of water and aprotic solvents. Croatica Chemica Acta [Internet]. 2012. [pristupljeno 15.04.2024.];85(4):585-594. doi: 10.5562/cca2179

M. Matić, B. Denegri i O. Kronja, "The reactivity of benzoates in mixtures of water and aprotic solvents", Croatica Chemica Acta, vol. 85, br. 4, str. 585-594, 2012. [Online]. Dostupno na: https://urn.nsk.hr/urn:nbn:hr:163:434972. [Citirano: 15.04.2024.]

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Podaci o radu
Naslov (engleski)The reactivity of benzoates in mixtures of water and aprotic solvents
AutorMirela Matić
AutorBernard Denegri
AutorOlga Kronja
Autorova ustanovaSveučilište u Zagrebu
Farmaceutsko-biokemijski fakultet
(Zavod za organsku kemiju)
Znanstveno / umjetničko
područje, polje i grana		PRIRODNE ZNANOSTI
Kemija
Organska kemija
Sažetak (engleski)
Nucleofugalities of pentafluorobenzoate (PFB), 2,4,6-trifluorobenzoate (TFB), 2-nitrobenzoate, and 3,5-dinitrobenzoate (DNB) leaving groups have been derived from the solvolysis rate constants of the corresponding X,Y-substituted Z-benzhydryl benzoates in 60 % and 80 % aqueous acetonitrile and 60 % aqueous acetone, by applying the LFER equation: log k = f s (Ef + Nf). The experimental barriers (ΔG‡ exp) for solvolyses of 13 dianisylmethyl Z-substituted benzoates in these solvents correlate very well with the ΔH‡ calc of the model epoxy ring formation (calculated earlier by the B3LYP-PCM quantum-chemical method). Using the ΔG‡ exp vs. ΔH‡ calc correlation, and taking f s based on similarity, the nucleofugality parameters for about 70 benzoates have been determined in 60 % and 80 % aqueous acetonitrile and 60 % aqueous acetone. Z-Substituents on the phenyl ring have larger impact on the solvolytic reactivity in the less polar solvent than in the more polar solvent due to the more carbocation-like transition state. (doi: 10.5562/cca2179)
Ključne riječi (engleski)
Jezikengleski
Vrsta publikacijeZnanstveni rad - Izvorni znanstveni rad
Status objaveObjavljen
Vrsta recenzijeRecenziran - međunarodna recenzija
Verzija publikacijeObjavljena verzija rada (izdavačev PDF)
Naslov časopisaCroatica Chemica Acta
Brojčani podacivol. 85, br. 4, str. 585-594
p-ISSN0011-1643
e-ISSN1334-417X
DOIhttps://doi.org/10.5562/cca2179
URN:NBNurn:nbn:hr:163:434972
Datum objave publikacije2012
URL dokumentahttps://hrcak.srce.hr/94471
Vrsta resursaTekst
Prava pristupaOtvoreni pristup
Uvjeti korištenjaIkona licence Zaštićeno autorskim pravom.
Datum i vrijeme pohrane2020-04-17 14:26:32