Rate-Product Correlations for the Solvolysis of 5-Nitro-2-Furoyl Chloride 


Vol. 33,  No. 10, pp. 3293-3297, Oct.  2012
10.5012/bkcs.2012.33.10.3293


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  Abstract

The solvolysis rate constants of 5-nitro-2-furoyl chloride (5-NO2(C4H2O)-2-COCl, 1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale and YCl solvent ionizing scale, with sensitivity values of 1.20 ± 0.05 and 0.37 ± 0.02 for l and m, respectively. The activation enthalpies (ΔH≠) were 5.63 to 13.0 kcal·mol−1 and the activation entropies (ΔS≠) were −25.9 to −43.4 cal·mol−1·K−1, which is consistent with the proposed bimolecular reaction mechanism. The solvent kinetic isotope effect (SKIE, kMeOH/kMeOD) of 2.65 was also in accord with the SN2 mechanism and was possibly assisted using a general-base catalysis. The product selectivity (S) for solvolysis of 1 in alcohol/water mixtures was 1.2 to 11, which is also consistent with the proposed bimolecular reaction mechanism.

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  Cite this article

[IEEE Style]

H. Choi, H. J. Koh, D. Ali, K. Yang,  . S. Koo, "Rate-Product Correlations for the Solvolysis of 5-Nitro-2-Furoyl Chloride," Bulletin of the Korean Chemical Society, vol. 33, no. 10, pp. 3293-3297, 2012. DOI: 10.5012/bkcs.2012.33.10.3293.

[ACM Style]

Hojune Choi, Han Joong Koh, Dildar Ali, Kiyull Yang, and  In Sun Koo. 2012. Rate-Product Correlations for the Solvolysis of 5-Nitro-2-Furoyl Chloride. Bulletin of the Korean Chemical Society, 33, 10, (2012), 3293-3297. DOI: 10.5012/bkcs.2012.33.10.3293.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949