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Kinetic and Mechanistic Elucidation of the Formation Reaction of 3,4,5-Substituted Furan-2(5H)-Ones in Formic Acid as the Solvent

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Abstract

For the first time, kinetics and mechanism of a one-pot multicomponent reaction between 4-methyl aniline 1 and diethyl acetylenedicarboxylate 2 with benzaldehyde 3 has been investigated spectroscopically in formic acid. The reaction followed second-order kinetics overall. Also, partial orders with respect to 4-methyl aniline 1, diethyl acetylenedicarboxylate 2 and benzaldehyde 3 are one, one and zero, respectively. Considering the kinetic results, a mechanism was proposed involving four steps. Furthermore, thermodynamic activation parameters and also kinetic values were obtained and examined at the various temperatures and solvents. The results show that the first step of the reaction mechanism is a rate-determining step.

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran

    Sayyed Mostafa Habibi-Khorassani, Mehdi Shahraki, Maryam Dehdab & Mohammad Ali Poorshamsoddin

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  1. Sayyed Mostafa Habibi-Khorassani
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  2. Mehdi Shahraki
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  3. Maryam Dehdab
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  4. Mohammad Ali Poorshamsoddin
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Correspondence to Sayyed Mostafa Habibi-Khorassani.

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Habibi-Khorassani, S.M., Shahraki, M., Dehdab, M. et al. Kinetic and Mechanistic Elucidation of the Formation Reaction of 3,4,5-Substituted Furan-2(5H)-Ones in Formic Acid as the Solvent. J Solution Chem 44, 2154–2166 (2015). https://doi.org/10.1007/s10953-015-0398-x

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