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Scientific paper - Original scientific paper
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. & 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, no. 4, 2012, pp. 585-594. https://doi.org/10.5562/cca2179

Matić, Mirela, Bernard Denegri and Olga Kronja. "The reactivity of benzoates in mixtures of water and aprotic solvents." Croatica Chemica Acta 85, no. 4 (2012): 585-594. https://doi.org/10.5562/cca2179

Matić, M., Denegri, B. and Kronja, O. (2012) 'The reactivity of benzoates in mixtures of water and aprotic solvents', Croatica Chemica Acta, 85(4), pp. 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 [cited 2024 December 29];85(4):585-594. doi: 10.5562/cca2179

M. Matić, B. Denegri and O. Kronja, "The reactivity of benzoates in mixtures of water and aprotic solvents", Croatica Chemica Acta, vol. 85, no. 4, pp. 585-594, 2012. [Online]. Available at: https://urn.nsk.hr/urn:nbn:hr:163:434972. [Accessed: 29 December 2024]

Metadata
Title (english)The reactivity of benzoates in mixtures of water and aprotic solvents
AuthorMirela Matić
AuthorBernard Denegri
AuthorOlga Kronja
Author's institutionUniversity of Zagreb
Faculty of Pharmacy and Biochemistry
(Department of organic chemistry)
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract (english)
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)
Keywords (english)
Languageenglish
Publication typeScientific paper - Original scientific paper
Publication statusPublished
Peer reviewPeer review - international
Publication versionPublished version
Journal titleCroatica Chemica Acta
Numberingvol. 85, no. 4, pp. 585-594
p-ISSN0011-1643
e-ISSN1334-417X
DOIhttps://doi.org/10.5562/cca2179
URN:NBNurn:nbn:hr:163:434972
Publication2012
Document URLhttps://hrcak.srce.hr/94471
Type of resourceText
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2020-04-17 14:26:32