297
Views
6
CrossRef citations to date
0
Altmetric
Research Article

Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one

, ORCID Icon, , , , , , , & show all
Pages 645-663 | Received 07 Feb 2021, Accepted 29 Jun 2021, Published online: 13 Jul 2021

References

  • Tomašić T, Peterlin Mašič L. Rhodanine as a scaffold in drug discovery: A critical review of its biological activities and mechanisms of target modulation. Expert Opin Drug Discov. 2012;7:549–560.
  • Tissaoui K, Raouafi N, Boujlel K. Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives. J Sulfur Chem. 2010;31:41–48.
  • Sabahi-Agabager L, Nasiri F. One-pot, solvent-free facile stereoselective synthesis of rhodanine–furan hybrids from renewable resources. J Sulfur Chem. 2020;41:170–181.
  • Brown FC. 4-Thiazolidinones. Chem Rev. 1961;61:463–521.
  • Singh SP, Parmar SS, Raman K, et al. Chemistry and biological activity of thiazolidinones. Chem Rev. 1981;81:175–203.
  • Andleeb H, Tehseen Y, Ali Shah SJ, et al. Identification of novel pyrazole-rhodanine hybrid scaffolds as potent inhibitors of aldose reductase: design, synthesis, biological evaluation and molecular docking analysis. RSC Adv. 2016;6:77688–77700.
  • Agrawal YP, Agrawal MY, Gupta AK. Design, synthesis and evaluation of rhodanine derivatives as aldose reductase inhibitors. Chem Biol Drug Des. 2015;85:172–180.
  • Chauhan K, Sharma M, Singh P, et al. Discovery of a new class of dithiocarbamates and rhodanine scaffolds as potent antifungal agents: synthesis, biology and molecular docking. MedChemComm. 2012;3:1104–1110.
  • Kumar G, Parasuraman P, Sharma SK, et al. Discovery of a rhodanine class of compounds as inhibitors of plasmodium falciparum enoyl-acyl carrier protein reductase. J Med Chem. 2007;50:2665–2675.
  • Muhammad SA, Ravi S, Thangamani A, et al. Synthesis, antiproliferative activity and docking study of novel rhodanine derivatives as Bcr-Abl T1351 inhibitors. Res Chem Intermed. 2017;43:5871–5887.
  • Sing WT, Lee CL, Yeo SL, et al. Arylalkylidene rhodanine with bulky and hydrophobic functional group as selective HCV NS3 protease inhibitor. Bioorganic Med Chem Lett. 2001;11:91–94.
  • El-Sayed S, Metwally K, El-Shanawani AA, et al. Synthesis and anticancer activity of novel quinazolinone-based rhodanines. Chem Cent J. 2017;11:102.
  • Krátký M, Vinšová J, Stolaříková J. Antimicrobial activity of rhodanine-3-acetic acid derivatives. Bioorganic Med Chem. 2017;25:1839–1845.
  • Wang L, Kong F, Kokoski CL, et al. Development of dimeric modulators for anti-apoptotic Bcl-2 proteins. Bioorganic Med Chem Lett. 2008;18:236–240.
  • Tejchman W, Korona-Glowniak I, Malm A, et al. Antibacterial properties of 5-substituted derivatives of rhodanine-3-carboxyalkyl acids. Med Chem Res. 2017;26:1316–1324.
  • Tintori C, Iovenitti G, Ceresola ER, et al. Rhodanine derivatives as potent anti-HIV and anti-HSV microbicides. Maga G, editor. PLoS One. 2018;13:e0198478.
  • Rajamaki S, Innitzer A, Falciani C, et al. Exploration of novel thiobarbituric acid-, rhodanine- and thiohydantoin-based HIV-1 integrase inhibitors. Bioorganic Med Chem Lett. 2009;19:3615–3618.
  • Sim MM, Ng SB, Buss AD, et al. Benzylidene rhodanines as novel inhibitors of UDP-N-acetylmuramate/L-alanine ligase. Bioorganic Med Chem Lett. 2002;12:697–699.
  • Ahn JH, Kim SJ, Park WS, et al. Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors. Bioorganic Med Chem Lett. 2006;16:2996–2999.
  • Cutshall NS, O’Day C, Prezhdo M. Rhodanine derivatives as inhibitors of JSP-1. Bioorganic Med Chem Lett. 2005;15:3374–3379.
  • Smith TK, Young BL, Denton H, et al. First small molecular inhibitors of T. brucei dolicholphosphate mannose synthase (DPMS), a validated drug target in African sleeping sickness. Bioorganic Med Chem Lett. 2009;19:1749–1752.
  • Liu J, Wu F, Chen L, et al. Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors. Bioorganic Med Chem Lett. 2011;21:2376–2379.
  • Grant EB, Guiadeen D, Baum EZ, et al. The synthesis and SAR of rhodanines as novel class C β-lactamase inhibitors. Bioorganic Med Chem Lett. 2000;10:2179–2182.
  • Shafii N, Khoobi M, Amini M, et al. Synthesis and biological evaluation of 5-benzylidenerhodanine-3-acetic acid derivatives as AChE and 15-LOX inhibitors. J Enzyme Inhib Med Chem. 2015;30:389–395.
  • Tomašić T, Zidar N, Kovač A, et al. 5-benzylidenethiazolidin-4-ones as multitarget inhibitors of bacterial Mur ligases. ChemMedChem. 2010;5:286–295.
  • Furdas SD, Shekfeh S, Kannan S, et al. Rhodanine carboxylic acids as novel inhibitors of histone acetyltransferases. Medchemcomm. 2012;3:305–311.
  • Solmaz R, Mert ME, Kardaş G, et al. Adsorption and corrosion inhibition effect of 1,1′-thiocarbonyldiimidazole on mild steel in H2SO4 solution and synergistic effect of iodide ion. Acta Phys – Chim Sin. 2008;24:1185–1191.
  • Solmaza R, Altunbaş E, Kardaş G. Investigation of adsorption and corrosion inhibition effect of 1,1’-thiocarbonyldiimidazole on mild steel in hydrochloric acid solution. Prot Met Phys Chem Surfaces. 2011;47:264–271.
  • Solmaz R, Kardaš G, Yažiči B, et al. Inhibition effect of rhodanine for corrosion of mild steel in hydrochloric acid solution. Prot Met. 2005;41:581–585.
  • Solmaz R. Investigation of adsorption and corrosion inhibition of mild steel in hydrochloric acid solution by 5-(4-dimethylaminobenzylidene)rhodanine. Corros Sci. 2014;79:169–176.
  • Eldesoky AM, El-Bindary MA, El-Sonbati AZ, et al. New eco-friendly corrosion inhibitors based on azo rhodanine derivatives for protection copper corrosion. J Mater Environ Sci. 2015;6:2260–2276.
  • Abdallah M. Rhodanine azosulpha drugs as corrosion inhibitors for corrosion of 304 stainless steel in hydrochloric acid solution. Corros Sci. 2002;44:717–728.
  • Tomasic T, Masic L. Rhodanine as a privileged scaffold in drug discovery. Curr Med Chem. 2009;16:1596–1629.
  • Morgan SM, Diab MA, El-Sonbati AZ. Synthesis, spectroscopic, thermal properties, Calf thymus DNA binding and quantum chemical studies of M(II) complexes. Appl Organomet Chem. 2018;32:e4281.
  • Mazza MT C, De Cicco L, De Rosa G, et al. Preparation and activity of complexes of transition metals and thiolic heterocyclic ligands. Boll Soc Ital Biol Sper. 1996;72:79–86.
  • Kshirsagar V, Gandhe S, Gautam MD. Electrochemical studies on ρ-dimethylaminobenzylidine rhodanine and its application as amperometric reagent. Rasayan J Chem. 2010;3:772–776.
  • Akram D, Elhaty IA, AlNeyadi SS. Synthesis and antibacterial activity of rhodanine-based azo dyes and their use as spectrophotometric chemosensor for Fe3+ ions. Chemosensors. 2020;8:16.
  • Ceylan A, Baş S, Bayrakcı M, et al. Synthesis and spectroscopic studies of novel rhodanine Azo dyes: An excellent selective chemosensor for naked-eye detecting of Cu2+ ion. Acta Chim Slov. 2012;59:656–663.
  • Echeverry CA, Insuasty A, Herranz MÁ, et al. Organic dyes containing 2-(1,1-dicyanomethylene)rhodanine as an efficient electron acceptor and anchoring unit for dye-sensitized solar cells. Dye Pigment. 2014;107:9–14.
  • Kim Y, Song CE, Moon SJ, et al. Rhodanine dye-based small molecule acceptors for organic photovoltaic cells. Chem Commun. 2014;50:8235–8238.
  • Anbarasan R, Dhandapani A, Manivarman S, et al. Synthesis and spectroscopical study of rhodanine derivative using DFT approaches. Spectrochim Acta – Part A Mol Biomol Spectrosc. 2015;146:261–272.
  • Baroudi B, Argoub K, Hadji D, et al. Synthesis and DFT calculations of linear and nonlinear optical responses of novel 2-thioxo-3-N,(4-methylphenyl) thiazolidine-4 one. J Sulfur Chem. 2020;41:310–325.
  • Dolgonos A, Mason TO, Poeppelmeier KR. Direct optical band gap measurement in polycrystalline semiconductors: a critical look at the Tauc method. J Solid State Chem. 2016;240:43–48.
  • Viezbicke BD, Patel S, Davis BE, et al. Evaluation of the Tauc method for optical absorption edge determination: ZnO thin films as a model system. Phys Status Solidi Basic Res. 2015;252:1700–1710.
  • Bouzourâa MB, Battie Y, En Naciri A, et al. N2+ ion bombardment effect on the band gap of anatase TiO2 ultrathin films. Opt Mater (Amst). 2019;88:282–288.
  • Ibrahim A, Al-Ani SKJ. Models of optical absorption in amorphous semiconductors at the absorption edge – a review and re-evaluation. Czechoslov J Phys. 1994;44:785–797.
  • Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100.
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09. Wallingford (CT): Gaussian, Inc.; 2009.
  • Adamo C, Barone V. Toward reliable density functional methods without adjustable parameters: The PBE0 model. J Chem Phys. 1999;110:6158–6170.
  • Yanai T, Tew DP, Handy NC. A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett. 2004;393:51–57.
  • Chai J-D, Head-Gordon M. Systematic optimization of long-range corrected hybrid density functionals. J Chem Phys. 2008;128:084106.
  • Zhao Y, Truhlar DG. Density functional for spectroscopy: No long-range self-interaction error, good performance for Rydberg and charge-transfer states, and better performance on average than B3LYP for ground states. J Phys Chem A. 2006;110:13126–13130.
  • Bishop DM, Norman P. Calculations of dynamic hyperpolarizabilities for small and medium-sized molecules. In: Nalwa HS, editor. Handbook of advanced electronic and photonic materials and devices. Academic, San Diego, Vol. 9 Elsevier; 2001. p. 1–62.
  • Hadji D, Champagne B. First principles investigation of the polarizability and first hyperpolarizability of anhydride derivatives. Chem Africa. 2019;2:443–453.
  • Hadji D, Rahmouni A. Molecular structure, linear and nonlinear optical properties of some cyclic phosphazenes: a theoretical investigation. J Mol Struct. 2016;1106:343–351.
  • Abdel-Latif SA, Moustafa H. Synthesis, spectroscopic properties, density functional theory calculations and nonlinear optical properties of novel complexes of 5-hydroxy-4,7-dimethyl-6-(phenylazo)coumarin with Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) metal ions. Appl Organomet Chem. 2018;32:e4269.
  • Abdel-Latif SA, Mohamed AA. Novel Zn(II) complexes of 1,3-diphenyl-4-(arylazo)pyrazol-5-one derivatives: synthesis, spectroscopic properties, DFT calculations and first order nonlinear optical properties. J Mol Struct. 2018;1156:712–725.
  • Abdel-Kader NS, Abdel-Latif SA, El-Ansary AL, et al. Spectroscopic studies, density functional theory calculations, non-linear optical properties, biological activity of 1-hydroxy-4-((4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)diazenyl)-2-naphthoic acid and its chelates with nickel (II), copper (II), zinc (II) and palladium (II) metal ions. J Mol Struct. 2021;1223:129203.
  • Abdel-Kader NS, Abdel-Latif SA, El-Ansary AL, et al. Combined experimental, DFT theoretical calculations and biological activity of sulfaclozine azo dye with 1-hydroxy-2-naphthoic acid and its complexes with some metal ions. New J Chem. 2019;43:17466–17485.
  • Bersohn R, Yoh-Han PAO, Frisch HL. Double-quantum light scattering by molecules. J Chem Phys. 1966;45:3184–3198.
  • Toubal K, Boukabcha N, Tamer Ö, et al. Spectroscopic (FT-IR, 1H and 13C NMR) characterization and density functional theory calculations for (Z)-5-(4-nitrobenzyliden)-3-N (2-ethoxyphenyl)-2-thioxo-thiazolidin-4-one (ARNO). J Mol Struct. 2017;1147:569–581.
  • Pegu D. Solvent effects on nonlinear optical properties of novel para-nitroaniline derivatives: a density functional approach. Int J Sci Res. 2014;3:469–474.
  • Al-Sehemi AG, EL-Gogary TM. Geometry and thermodynamic stabilities of rhodanine tautomers and rotamers: quantum chemical study. J Mol Struct Theochem. 2009;907:66–73.
  • Fernandes SSM, Herbivo C, Aires-de-Sousa J, et al. Theoretical and experimental studies of aryl-bithiophene based push-pull π-conjugated heterocyclic systems bearing cyanoacetic or rhodanine-3-acetic acid acceptors for SHG nonlinear optical applications. Dye Pigment. 2018;149:566–573.
  • Adamo C, Cossi M, Scalmani G, et al. Accurate static polarizabilities by density functional theory: assessment of the PBE0 model. Chem Phys Lett. 1999;307:265–271.
  • Sabirov DS. Polarizability of C60 fullerene dimer and oligomers: The unexpected enhancement and its use for rational design of fullerene-based nanostructures with adjustable properties. RSC Adv. 2013;3:19430–19439.
  • Hadji D, Rahmouni A, Hammoutène D, et al. First theoretical study of linear and nonlinear optical properties of diphenyl ferrocenyl butene derivatives. J Mol Liq. 2019;286:110939.
  • Yang Y, Wang F-H, Zhou Y-S, et al. Density functional calculations of the polarizability and second-order hyperpolarizability of C50Cl10. Phys Rev A. 2005;71:13202.
  • Gopi V, Subbiahraj S, Chemmanghattu K, et al. 2,3-di(2-furyl) quinoxaline bearing 3 -ethyl rhodanine and 1,3 indandione based heteroaromatic conjugated T-shaped push -pull chromophores: design, synthesis, photophysical and non-linear optical investigations. Dye Pigment. 2020;173:107887.
  • Aihara JI. Reduced HOMO-LUMO gap as an index of kinetic stability for polycyclic aromatic hydrocarbons. J Phys Chem A. 1999;103:7487–7495.
  • Hadji D, Haddad B, Brandán SA, et al. Synthesis, NMR, Raman, thermal and nonlinear optical properties of dicationic ionic liquids from experimental and theoretical studies. J Mol Struct. 2020;1220:128713.
  • Hadji D, Brahim H. Structural, optical and nonlinear optical properties and TD-DFT analysis of heteroleptic bis-cyclometalated iridium(III) complex containing 2-phenylpyridine and picolinate ligands. Theor Chem Acc. 2018;137:180.
  • Boukabene M, Brahim H, Hadji D, et al. Theoretical study of geometric, optical, nonlinear optical, UV–Vis spectra and phosphorescence properties of iridium(III) complexes based on 5-nitro-2-(2′,4′-difluorophenyl)pyridyl. Theor Chem Acc. 2020;139:47.
  • Merouane A, Mostefai A, Hadji D, et al. Theoretical insights into the static chemical reactivity and NLO properties of some conjugated carbonyl compounds: case of 5-aminopenta-2, 4-dienal derivatives. Monatshefte für Chemie-Chemical Mon. 2020;151:1095–1109.
  • Hadji D, Rahmouni A. Theoretical study of nonlinear optical properties of some azoic dyes. Mediterr J Chem. 2015;4:185–192.
  • Hadji D. Phosphates branching effect on the structure, linear and NLO properties of linear phosphazenes. Mater Chem Phys. 2021;262:124280.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.