Effect of different substituents on the one-pot formation of 3,4,5-substituted furan-2(5H)-ones: a kinetics and mechanism studyElectronic supplementary information (ESI) available. See DOI: 10.1039/c5ra09717g

• Main Authors: Shahraki, Mehdi, Habibi-Khorassani, Sayyed Mostafa, Dehdab, Maryam
• Format: Journal Article
• Language: English
• Published: 16.06.2015
• ISSN: 2046-2069
• DOI: 10.1039/c5ra09717g

The kinetics of reactions between benzaldehyde and diethyl acetylenedicarboxylate with para -substituted anilines for the one-pot formation of 3,4,5-substituted furan-2(5 H )-ones have been studied spectrally at different temperatures in formic acid. For all substituents at the para position of the aniline ring, the reaction followed second-order kinetics. The partial orders with respect to substituted aniline and diethyl acetylenedicarboxylate were one and one, and the reactions also revealed zero-order kinetics in relation to benzaldehyde. Para -electron donating substituents on the aniline ring increased the rate of reaction. On the basis of experimental data, a three step mechanism has been proposed. Kinetic values ( k and E a ) and associated activation parameters (Δ H ≠ , Δ G ≠ and Δ S ≠ ) of the reactions were determined. This work focused on the effects of temperature and different para -substituted anilines on the activation parameters and kinetics of the synthesis reaction of 3,4,5-substituted furan-2(5 H )-ones which were studied spectrally at different temperatures in formic acid.