Izvorni znanstveni članak

https://doi.org/10.5562/cca2767

Molecular Structure of Phenytoin: NMR, UV-Vis and Quantum Chemical Calculations

Raluca Luchian ; Babeş-Bolyai University, Faculty of Physics, 1 Kogălniceanu, RO-400084 Cluj-Napoca, Romania
Emil Vinţeler ; Babeş-Bolyai University, Faculty of Physics, 1 Kogălniceanu, RO-400084 Cluj-Napoca, Romania
Cosmina Chiş ; Iuliu Haţieganu University of Medicine and Pharmacy, 8 Victor Babeş, RO-400012 Cluj-Napoca, Romania
Mihai Vasilescu ; Babeş-Bolyai University, Faculty of Physics, 1 Kogălniceanu, RO-400084 Cluj-Napoca, Romania
Nicolae Leopold ; Babeş-Bolyai University, Faculty of Physics, 1 Kogălniceanu, RO-400084 Cluj-Napoca, Romania
Vasile Chiş orcid.org/0000-0002-0935-4134 ; Babeş-Bolyai University, Faculty of Physics, 1 Kogălniceanu, RO-400084 Cluj-Napoca, Romania

Sažetak

Due to the presence of the carbonyl and imide groups in the structure of 5,5-diphenylhydantoin (DPH), the possibility for this compound to be involved in hydrogen bonding intermolecular interactions is obvious. Even though such interactions are presumably responsible for the mechanism of action of this drug, however, to the best of our knowledge, the self-hydrogen bonding interactions between the DPH monomers have not been addressed till now. Furthermore, studies reporting on the spectroscopic characteristics of this molecule are scarcely reported in the literature.
Here we report on the possible dimers of DPH, investigated by quantum chemical calculations at B3LYP/6-31+G(2d,2p) level of theory. Twelve unique DPH dimers were structurally optimized in gas-phase, as well as in ethanol and DMSO and then were used to compute the population-averaged UV-Vis and NMR spectra using Boltzmann statistics. UV-Vis and NMR techniques were employed to assess experimentally the spectroscopical response of this compound. DFT calculations are also used to investigate the structural transformations between the solid and liquid phase, as well as for describing the electronic transitions and for the assignment of NMR spectra of DPH.

Ključne riječi

5,5-diphenylhydantoin; hydrogen-bonded dimers; electronic transition; NMR

Hrčak ID:

154169

URI

https://hrcak.srce.hr/154169

Datum izdavanja:

31.12.2015.

Posjeta: 3.982 *