Experimental and quantum chemical study on the IR, UV and electrode potential of 6-(2,3-dihydro-1,3-dioxo-2-phenyl-1H-inden-2-yl)-2,3-dihydroxybenzaldehyde.
Electrode potential of 6-(2,3-dihydro-1,3-dioxo-2-phenyl-1H-inden-2-yl)-2,3-dihydroxybenzaldehyde (DPDB) in methanol have been calculated theoretically. For the achievement of this task, the density functional theory (B3LYP/6-31G(d)) was employed with the inclusion of the entropic and thermochemical corrections to yield the free energies of the redox reactions. The electrode potential was also obtained experimentally by means of an electrochemical technique (cyclic voltammetry). The geometric parameters, the vibrational frequency values and the UV spectrum of DPDB and 2-(2,3-dihydro-1,3-dioxo-2-phenyl-1H-inden-2-yl)-5,6-dioxocyclohexa-1,3-dienecarbaldehyde (DPDD is the oxidized form of DPDB), were computed using the same methods. The calculated IR spectrum of DPDB, used for the assignment of the IR frequencies, was observed in the experimental FT-IR spectrum. The correlation between the theoretical and experimental DPDB vibrational frequencies was 0.996. This agreement mutually verified the accuracy of the experimental method and the validity of the applied mathematical model.
Institute of Petroleum Engineering, Faculty of Engineering, University of Tehran, P.O. Box 11365-4563 Tehran, Iran. riahisv@khayam.ut.ac.ir
Siavash
S
Riahi
Mohammad Reza
MR
Ganjali
Abdolmajid
A
Bayandori Moghaddam
Parviz
P
Norouzi
D001547:Benzaldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D004563:Electrochemistry / Q000379:methods; D004566:Electrodes; D005898:Glass; D007189:Indans / Q000737:chemistry*; D008956:Models, Chemical; D008962:Models, Theoretical; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods*; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics
C538815:6-(2,3-dihydro-1,3-dioxo-2-phenyl-1H-inden-2-yl)-2,3-dihydroxybenzaldehyde; D001547:Benzaldehydes; D007189:Indans; D002244:Carbon