Novel route for the synthesis of azepine derivative using tin-based catalyst: Spectroscopic characterization and theoretical investigations

Kollur, Shiva Prasad and Costa, Renyer and Branches, Adjane D.S and Oliveira, Kelson M.T. (2018) Novel route for the synthesis of azepine derivative using tin-based catalyst: Spectroscopic characterization and theoretical investigations. Journal of Molecular Structure, 1178. pp. 491-499. ISSN 0022-2860

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Abstract

Synthesis of azepine-based compounds are of highly interest due to their vast applications in medicinal filed. In this work, is described the synthesis of a azepine-based derivative, 11-methoxy-6,6a-dihydro-5H-dibenzo[b,e]azepine (MDDA) by new route using dibutyltin dilaurate (DBTDL) as catalyst. The structural elucidation of MDDA was done by FT-IR, 1H NMR, and mass spectrometry techniques. Also is presented the experimental and theoretical DFT study of the vibrational, structural and quantum properties of MDDA using B3LYP exchange-correlation functional with 6-311G (2d, p) basis set. The theoretical DFT geometry optimization data was compared with the X-ray data in the associated literature promoting a good comprehension of the structural arrangement. In complementation, mapped molecular electrostatic potential surface (MEPS), HOMO-LUMO orbitals and NBO energy calculations were also performed using the same calculation approach. The calculated UV spectrum is in good agreement with the experimental one, making the bands assignments possible. The comparative IR studies clearly confirmed the intermolecular hydrogen bonds of the proposed dimeric form for MDDA and also showed several characteristic vibrations within the molecular structure.

Item Type: Article
Uncontrolled Keywords: Azepine, Spectroscopy, Electronic structure, HOMO-LUMO, DFT calculations.
Subjects: Departments at MU > Manipal Centre for Natural Sciences
Depositing User: MCNS Editor
Date Deposited: 29 Oct 2018 05:51
Last Modified: 29 Oct 2018 05:51
URI: http://eprints.manipal.edu/id/eprint/152187

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