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Open AccessArticle

A DFT Study of the Photochemical Dimerization of Methyl 3-(2-Furyl)acrylate and Allyl Urocanate

Dipartimento di Scienze, Università della Basilicata, Viale dell'Ateneo Lucano 10, 85100 Potenza, Italy
Molecules 2014, 19(12), 20482-20497; https://doi.org/10.3390/molecules191220482
Received: 12 September 2014 / Revised: 20 November 2014 / Accepted: 1 December 2014 / Published: 8 December 2014
(This article belongs to the Section Organic Chemistry)
A DFT study of the photochemical dimerization of methyl 3-(2-furyl)acrylate is reported. The photochemical reaction gave a mixture of two dimers with high regioselectivity and good stereoselectivity. Calculations showed that benzophenone was able to act as a photosensitizer of the reaction. This compound populated the first excited triplet state of the substrate. The frontier orbitals interaction between LSOMO of the triplet state and HOMO of the ground state accounted for the observed high regioselectivity. Furthermore, the energy of all the possible triplet biradicals has been calculated, showing that the precursor of the main product was the triplet biradical with the lowest energy. The coupling of the atomic coefficients on the radical centres in the biradical intermediates allowed to justify the observed products. The same behavior was observed in the case of the photochemical dimerization of an urocanate ester and in the dimerization of liquid methyl cinnamate. View Full-Text
Keywords: photochemical dimerization; 3-(2-furyl)acrylates; urocanates; cinnamates; DFT photochemical dimerization; 3-(2-furyl)acrylates; urocanates; cinnamates; DFT
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MDPI and ACS Style

D'Auria, M. A DFT Study of the Photochemical Dimerization of Methyl 3-(2-Furyl)acrylate and Allyl Urocanate. Molecules 2014, 19, 20482-20497.

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