Mechanism and Thermodynamic Parameters of Paternὸ-Büchi Reaction of Benzene and Furan: DFT Study

The Paternὸ-Büchi reaction of benzene with benzaldehyde and furan with furfural were studied theoretically. The mechanism was investigated using Density Functional Theory (DFT). It was found that the final product of the benzene reaction is oxetane 3, while in the case of furan the oxetane 6 is unst...

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Bibliographic Details
Published in2018 International Conference on Advanced Science and Engineering (ICOASE) pp. 415 - 419
Main Authors Salim, Haydar Mohammad, Abdallah, Hassan H., Ramasami, P.
Format Conference Proceeding
LanguageEnglish
Published IEEE 01.10.2018
Subjects
benzene
Biology
Chemistry
Compounds
DFT
Discrete Fourier transforms
furan
mechanism
Orbits
Oxetane
Paternὸ-Büchi
thermodynamic parameters
Thermodynamics
Vibrations
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Summary:The Paternὸ-Büchi reaction of benzene with benzaldehyde and furan with furfural were studied theoretically. The mechanism was investigated using Density Functional Theory (DFT). It was found that the final product of the benzene reaction is oxetane 3, while in the case of furan the oxetane 6 is unstable and goes through oxetane ring opening. The target of this article was to study the reaction mechanism and calculate the thermodynamic parameters of the reactions. The oxetane 3 formed was found to be stable with reaction energy of -120 kcal/mol. However, the oxetane 6 was found to be less stable with reaction energy 21 kcal/mol which tends to produce more stable product 7 through the oxetane ring opening. In addition, the molecular orbitals were calculated and analyzed for all the intermediates, oxetanes and final products.
DOI:10.1109/ICOASE.2018.8548917