Investigation of the Effects of Solvents on the Structural, Electronic and Thermodynamic Properties of Rosiglitazone Based on Density Functional Theory

Abstract

Rosiglitazone ( C18H19N3O3S ) is an anti-diabetic drug that reduces insulin resistance in patients with type 2 diabetes. The parameters (bond lengths and bond angles), HOMO, LUMO, HOMO-LUMO energy gap, dipole moment, thermodynamic properties, total energy and vibrational frequencies and intensities of the Rosiglitazone molecule in gas phase and in solvents (Water, Ethanol, DMSO and Acetonitrile) were calculated based on Density Functional Theory (DFT) using standard basis sets: B3LYP/6-31G(d,p), B3LYP/6-31+G(d,p) and B3LYP/6-31++G(d,p). Windows version of Gaussian 09 was used for all the calculations. From the results obtained, the solvents have little influence on the optimized parameters of the molecule. The highest HOMO value of -5.433 eV was found in gas phase showing that the molecule will best donate electron in the gas phase, followed by ethanol in comparison with other solvents. The values of the HOMO were observed to increase with the decrease in dielectric constants of the solvents across all the basis sets used. The lowest LUMO energy of -1.448 eV was found to be in ethanol which shows that the molecule will best accept electron in ethanol compared to the gas phase and other solvents. The largest HOMO-LUMO gap of 4.285 eV was found in water which shows its higher kinetic stability and less chemical reactivity compared to other solvents and in the gas phase. The chemical softness of the molecule was found to decrease as the dielectric constants of the solvents increased namely from ethanol to water. The chemical hardness was found to slightly increase with the increase in dielectric constants of the solvents. The highest value of the dipole moment of 4.6874 D was found in water indicating that the molecule will have the strongest intermolecular interactions in water compared to other solvents and in the gas phase. The total energy increased as the dielectric constants of the solvents decreased from water to ethanol. The vibrational frequencies and intensities increased as the dielectric constants of the solvents increased from ethanol to water. The results confirmed the effects of solvents on the structural, electronic and thermodynamic properties of the studied molecule and will be useful in the design and development of rosiglitazone as an anti-diabetic drug.

Molecular Structure and Electronic Properties of Some Phenylalanine Derivatives as Tryptophan Hydroxylas (Tph) Inhibitors

“…This reduction in turn led to a decrease in hardness from 2.11 eV to 2 eV and an increase in activity from 6.72 to 7.89 for compounds 1 and 2 respectively. This judgment is also supported by a prior report, which stated that higher HOMO-LUMO energy gap values corresponded to higher stability [7].…”

Density Functional Theory Investigation of the Doping Effects of Bromine and Fluorine on the Electronic and Optical Properties of Neutral and Ionic Perylene

“…The HOMO and LUMO energy gap values of the neutral and ionic forms of the isolated and mono-halogenated Perylene are presented in Table 2 for the two basis sets under study. Compounds with large HOMO-LUMO energy gap values are found to have low reactivity and high kinetic stability [5]. The lower the energy gap, of a molecule the easier it is for an electron to be emitted from the ground state [15].…”

“…This development is because of the strong optical absorption, mechanical flexibility, low cost and solubility these materials exhibit [4]. Perylene (C 20 H 12 ) and its derivatives such as Perylene bisimide, Perylene tetracarboxylic acid (PTDCA) and Perylene 3,4,9,10tetracarboxylic acid (PDA) have found vast application in organic photovoltaics, organic fieldeffect transistors (OFET), sensors and molecular spectroscopy because of their promising electronic, optical and charge transport properties [5].…”

“…The study of the effect of mono halogenation on the electron properties of Perylene diimides X-PDI (X= F, H, Br and Cl) showed an increase in the electron mobilities of the hybrids in order of F-PDI> H-PDI> Cl-PDI = Br-PD [11]. The solvent effects on structural, electronic and non-linear optical were investigated by [5]. They showed that the bond lengths, energy gap, anisotropic hyper-polarizability increase as the polarity increases while the bond angle and polarizability decrease as the polarity increases.…”

Theoretical Study for Chemical Reactivity Descriptors of Tetrathiafulvalene in gas phase and solvent phases based on Density Functional Theory

“…In the recent years, the Density Functional Theory (DFT), has been the most common quantum chemical method used for calculating different molecular properties such as physical, chemical and biological systems [9,10] . Chemical descriptors were described by DFT for studying and forecasting reactivity indices and selectivity [11][12][13][14][15][16][17][18] . The objective of this study is to analyze Frontier Molecular Orbitals (FMOs) energies and obtain global reactivity descriptors.…”