Restricted accessResearch articleFirst published online 2017-11
Assessment of various density functionals and solvation models to describe acid-base,spectral and complexing properties of thiobarbituric and barbituric acids in aqueous solution
The current research deal with ab initio calculations of equilibrium constants of stability or dissociation and some spectral properties of 2-thiobarbituric and barbituric acids. 11 DFT functionals (revTPSS, TPSSh, PBE, revPBE, M06-L, M06, M06-2X, M05-2X, M06-HF, CAM-B3LYP, X3LYP) with cc-pVDZ basis set were used for calculations of and . For each of functionals the calculations were carried out for three solvation models – SMD, COSMO and C-PCM. It has been found that functionals containing 55% Hartree-Fock exchange (M06-2X and M05-2X) provide a better approach. The TD-DFT calculations show that revTPSS and TPSSh give accurate results for the description of the spectral characteristics. The revTPSS/CRNBL ECP/SMD level was tested for evaluating parameters of complex formation process these acids with La(III) for various computational models.
LaxmiS.RajithaG. and RajithaB., Photochemical synthesis and anticancer activity of barbituric acid, thiobarbituric acid, thiosemicarbazide, and isoniazid linked to 2-phenyl indole derivatives, J Chem Biol15 (2015), 1–7.
2.
GoutziomitrouaE.VenetisbC. and KolibianakisaE., Propofol versus thiopental sodium as anaesthetic agents for oocyte retrieval: A randomized controlled trial Reproductive, BioMedicine Online31 (2015), 752–759.
3.
XiongZ.SunD.-W.PuH.XieA.HanZ. and LuoM., Non-destructive prediction of thiobarbituric acid reactive substances (TBARS) value for freshness evaluation of chicken meat using hyperspectral imaging, Food Chemistry179 (2015), 175–181.
4.
MurphyJ. and SvehlaG., An analytical study of metal – thiobarbituric acid complexes, Analytica Chimica Acta99 (1978), 115–124.
5.
KhalidM.FazalR.KhanaA. and ShabeerbM., Synthesis and structure – activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease, Bioorganic & Medicinal Chemistry22 (2014), 4119–4123.
6.
TsaiM.-C. and HuangT.-L., Thiobarbituric acid reactive substances (TBARS) is a state biomarker of oxidative stress in bipolar patients in a manic phase, Journal of Affective Disorders173 (2015), 22–26.
7.
TürkelN. and Suat-AksoyM., Complex formation of Nickel(II) and Copper(II) with barbituric acid, Analytical Chemistry2014 (2014), 5.
8.
O’NeilI.A., Science of synthesis: Houben-Weyl Methods of Molecular Transformations. Organometallics. Compounds of group 12 and 11(Zn. Cd. Cu. Ag. Au), Ley. S.V., George Theme Verla, Stuttgart, 2004, 773.
9.
TabassumS.SiddiqiK.S. and KhanN.H., Studies on barbituric acid complexes of lanthanide ions, Indian J Chem26 (1987), 523.
10.
TabassumS.SiddiqiK.S.KhanN.H. and KureshyR.I., Studies on complexes of thiobarbituric and 5, 5-diethylbarbituric acid with Lanthanide ions, Indian J Chem26 (1987), 489.
11.
MasoudM.S. and El-DessoukyM.A., Transition metal (disubstitutedphenylazo)-barbituric and thiobarbituric acid complexes, Transition Metal Chemistry15 (1990), 443–448.
12.
LiX.WuD.GuY. and GanF., Synthesis, spectral and thermal properties of some transition metal(II) complexes with a novel ligand derived from thiobarbituric acid, Journal of Thermal Analysis and Calorimetry98 (2009), 387–394.
13.
LutoshkinM.A.PetrovA.I. and GolovnevN.N., Acid – Base, complexing and spectral properties of thiobarbituric acid and its 1, 3-derivatives in aqueous solutions: Spectrophotometric and quantum chemical approach, J Solution Chem45 (2016), 1453–1467.
14.
ZambrzyckaE. and Godlewska-ŻyłkiewiczB., A new ion imprinted polymer based on Ru(III)-thiobarbituric acid complex for solid phase extraction of ruthenium(III) prior to its determination by ETAAS, Mikrochim Acta1027 (2014), 181–1019.
15.
HosseinzadehaB.BeniaA.S.ChermahinibA.N.GhaharycR. and TeimouridA., Novel organic dyes with anchoring group of barbituric/thiobarbituric acid and their application in dye-sensitized solar cells, Synthetic Metals209 (2015), 1–10.
16.
ThapaB. and SchlegelH.B., Calculating free energy changes in continuum solvation models, J Phys Chem A120 (2016), 5726–5735.
17.
Rebollar-ZepedaA.M. and GalanoA., Quantum mechanical based approaches for predicting pKa values of carboxylic acids: Evaluating the performance of different strategies, RSC Adv6 (2016), 112057–112064.
18.
SeniorS.A. and NassarA.M., Determination of pKa for substituted benzoic acids in mixed solvent using density functional theory and QSPR, Int J Quantum Chem112 (2012), 683–694.
19.
MikkelsenK.V. and RatnerM.A., Specific solvation effects on electron transfer, Int J Quantum Chem34 (1988), 707–720.
20.
LutoshkinM.A. and GolovnevN.N., Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1, 3-diethyl-2-thiobarbituric acid, Heterocycl Commun22 (2016), 111–116.
21.
SchmidtM.W. et al., General atomic and molecular electronic structure system, S ComputChem14 (1993), 1347–1363.
22.
DunningT.H., Jr., Gaussian basis sets for use in correlated molecular calculations, I, The atoms boron through neon and hydrogen, J Chem Phys90 (1989), 1007–1023.
23.
RossR.B. et al., Erratum: Ab initio relativistic effective potentials with spin – orbit operators, IV Cs through, J Chem Phys93 (1990), 6654–6668.
24.
MarenichA.V.CramerC.J. and TruhlarD.G., Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions, J Phys Chem113 (2009), 6378–6396.
25.
KlamtA., Conductor-like screening model for real solvents: A new approach to the quantitative calculation of solvation phenomena, J Phys Chem99 (1995), 2224–2235.
26.
TakanoY. and HoukK.N., Benchmarking the conductor-like polarizable continuum model (CPCM) for aqueous solvation free energies of neutral and ionic organic molecules, J Chem Theory Comput1 (2005), 70–77.
27.
YangK.ZhengJ.ZhaoY. and TruhlarD.G., Tests of the RPBE, revPBE, t-HCTHhyb, wB97X-D, and MOHLYP density functional approximations and 29 others against representative databases for diverse bond energies and barrier heights in catalysis, J Phys Chem132 (2010), 164117.
28.
PerdewJ.P.RuzsinszkyA.CsonkaG.I. and ConstantinL.A., Workhorse semilocal density functional for condensed matter physics and quantum chemistry, Phys Rev Lett106 (2011), 179902.
29.
TaoJ.PerdewJ.P.StaroverovV.N. and ScuseriaG.E., Climbing the density functional ladder: Nonempirical meta – generalized gradient approximation designed for molecules and solids, Phys Rev Lett91 (2003), 146401.
30.
PerdewJ.P.BurkeK. and ErnzerhofM., Generalized gradient approximation made simple, Phys Rev Lett77 (1996), 3865.
31.
ZhaoY. and TruhlarD.G., A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions, J Chem Phys125 (2006), 194101.
32.
ZhaoY. and TruhlarD.G., The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals, TheorChem Account120 (2008), 215–241.
33.
ZhaoY.SchultzN.E. and TruhlarD.G., Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions, J Chem Theory Comput2 (2005), 364–382.
34.
WalkerM.HarveyA.A. and SenA., Performance of M06, M06-2X, and M06-HF density functionals for conformationally flexible anionic clusters: M06 functionals perform better than B3LYP for a model system with dispersion and ionic hydrogen-bonding interactions, J Phys Chem A117 (2013), 12590–12600.
35.
ZhangY. and YangW., Comment on “generalized gradient approximation made simple”, Phys Rev Lett80 (1998), 890.
36.
YanaiT.TewD.P. and HandybN.C., A new hybrid exchange – correlation functional using the Coulomb-attenuating method (CAM-B3LYP), Chemical Physics Letters393 (2004), 51–57.
37.
XuX. and GoddardW.A., The X3LYP extended density functional for accurate descriptions of non bond interactions, spin states, and thermochemical properties, Proceedings of the National Academy of Sciences of the United States of America101 (2003), 2673–2677.
38.
CrugeirasJ.RíosA. and MaskillH.J., DFT and AIM study of the protonation of nitrous acid and the pKa of nitrous acidium ion, Phys Chem115 (2011), 12357–12363.
39.
BryantsevV.S.MamadouS.D. and GoddardW.A., Calculation of solvation free energies of charged solutes using mixed cluster/continuum models, J Phys Chem B112 (2008), 9709–9719.
40.
VukovicS.HayB.P. and BryantsevV.S., Predicting stability constants for uranyl complexes using density functional theory, Theory Inorg Chem54 (2015), 3995–4001.
41.
Tellez-SotoC.A.RamosJ.M. and JuniorA.C., Surface enhancement Raman scattering of tautomeric thiobarbituric acid. Natural bond orbitals and B3LYP/6311+G(d, p) assignments of the fourier infrared and fourier raman spectra, Spectrochim Acta A: Molec Biomolec Spectr114 (2013), 475–485.
42.
IzquierdoA.BeltranJ.L. and GuiterasJ., Thermodynamic properties of the dissociation of 2-mercaptopyridine, 2-mercaptopyrimidine and 2-thiobarbituric acid, Thermochimica Acta127 (1988), 81–88.
43.
BlaisM.S.EneaO. and BerthonG., Relations structure-réactivité grandeurs thermodynamiques de protonation d’h’et’erocyclessaturés et non saturés, Thermochim Acta20 (1977), 335.
44.
ZuccarelloF.BuemiG.GandolfoC. and ContinoA., Barbituric and thiobarbituric acids: A conformational and spectroscopic study, SpectrochimicaActa59 (2003), 139–151.
45.
PetrovA.I.LutoshkinM.A. and TaydakovI.V., Aqueous complexation of Y(III), La(III), Nd(III), Sm(III), Eu(III), and Yb(III) with some heterocyclic substituted β-Diketones, Eur J Inorg Chem6 (2015), 1074–1082.
