Synthesis, Structural Characterization and Theoretical NLO Activity of N-(4-Acetyl-5-(4-(Nitro) Phenyl)-4,5-Dihydro-1,3,4-Thiadiazol-2-yl)-N-Phenyl Acetamide

References

• A. Chouaih, F. Hamzaoui, and G. Vergoten, “Capability of X-Ray Diffraction to the Determination of the Macroscopic Linear Susceptibility in a Crystalline Envi- Ronment: The Case of 3-Methyl 4-Nitropyridine N-Oxide (POM),” Journal of Molecular Structure 738, no. 1–3 (2005): 33–8.
   Web of Science ®Google Scholar
• O. Kourat, A. Djafri, N. Benhalima, Y. Megrouss, N.E.H. Belkafouf, R. Rahmani, J.-C. Daran, A. Djafri, and A. Chouaih, “Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Spectral Characterization, Reduced Density Gradient and Nonlinear Optical Investigation on (E)-N’-(4-Nitrobenzylidene)-2-(Quinolin-8-Yloxy) Acetohydrazide Monohydrate: A Combined Experimental and DFT Approach,” Journal of Molecular Structure 1222 (2020): 128952.
   Web of Science ®Google Scholar
• M. Saidj, A. Djafri, R. Rahmani, N.E H. Belkafouf, N. Boukabcha, A. Djafri, and A. Chouaih, “Molecular Structure, Experimental and Theoretical Vibrational Spectroscopy, (HOMO-LUMO, NBO) Investigation, (RDG, AIM) Analysis, (MEP, NLO) Study and Molecular Docking of Ethyl-2-{[4-Ethyl-5-(Quinolin-8-yloxyMethyl)-4H-1,2,4-Triazol-3-yl] Sulfanyl} Acetate,” Polycyclic Aromatic Compounds (2022): 1–25.
   Web of Science ®Google Scholar
• B.A.D. Neto, A.A.M. Lapis, E.N. da Silva Júnior, and J. Dupont, “2,1,3-Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules,” European Journal of Organic Chemistry 2013, no. 2 (2013): 228–55.
   Web of Science ®Google Scholar
• C.H. Atchialefack Alongamo, N.K. Nkungli, and J.N. Ghogomu, “DFT-Based Study of the Impact of Transition Metal Coordination on the Charge Transport and Nonlinear Optical (NLO) Properties of 2-{[5-(4-Nitrophenyl)-1,3,4-Thiadiazol-2-Ylimino]Methyl}Phenol,” Molecular Physics 117, no. 18 (2019): 2577–92.
   Web of Science ®Google Scholar
• J.L. Brédas, “Molecular Geometry and Nonlinear Optics,” Science 263, no. 5146 (1994): 487–8.
   PubMed Web of Science ®Google Scholar
• L. Jensen, K.O. Sylvester-Hvid, K.V. Mikkelsen, and P.-O. Åstrand, “A Dipole Interaction Model for the Molecular Second Hyperpolarizability,” The Journal of Physical Chemistry A 107, no. 13 (2003): 2270–6.
   Web of Science ®Google Scholar
• P.N. Prasad and D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers (NewYork: Wiley, 1991).
   Google Scholar
• K. Yanagi, T. Kobayashi, and H. Hashimoto, “Origin of Transition Dipole-Moment Polarizability and Hyperpolarizability in Hydrazones,” Physical Review B 67, no. 11 (2003): 115–22.
   Web of Science ®Google Scholar
• E.M. Breitung, C.F. Shu, and R.J. Mc Mahon, “Thiazole and Thiophene Analogues of Donor-Acceptor Stilbenes: molecular Hyperpolarizabilities and Structure-Property Relationships,” Journal of the American Chemical Society 122, no. 6 (2000): 1154–60.
   Web of Science ®Google Scholar
• J.L. Hua, J. Li, and J.D. Luo, “Recent Progress in Molecular Design of Organic Second-Order Nonlinear Optical Chromophores with Both Large First-Order Molecular Hyperpolarizability and Good Transparency,” Chinese Journal of Organic Chemistry 23 (2003): 44–53.
   Web of Science ®Google Scholar
• M. Gür, H. Muğlu, M.S. Çavuş, A. Güder, H.S. Sayıner, and F. Kandemirli, “Synthesis, Characterization, Quantum Chemical Calculations and Evaluation of Antioxidant Properties of 1, 3, 4-Thiadiazole Derivatives Including 2-and 3-Methoxy Cinnamic Acids,” Journal of Molecular Structure 1134 (2017): 40–50.
   Web of Science ®Google Scholar
• N. Polkam, P. Rayam, J.S. Anireddy, S. Yennam, H.S. Anantaraju, S. Dharmarajan, Y. Perumal, S.S. Kotapalli, R. Ummanni, and S. Balasubramanian, “Synthesis, in Vitro Anticancer and Antimycobacterial Evaluation of New 5-(2, 5-Dimethoxyphenyl)-1, 3, 4-Thiadiazole-2-Amino Derivatives,” Bioorganic & Medicinal Chemistry Letters 25, no. 7 (2015): 1398–402.
   PubMed Web of Science ®Google Scholar
• A. Kumar Pandey, D. Vikram Shukla, V. Singh, and V. Narayan, “Structural, IR Spectra NBO, TDDFT, AIM Calculation, Biological Activity and Docking Property of [1,2,4]-Triazolo[3,4-b][1,3,4] Thiadiazole,” Egyptian Journal of Basic and Applied Sciences 5, no. 4 (2018): 280–8.
   Google Scholar
• A.K. Pandey, V. Baboo, V. Narayan Mishra, V.K. Singh, and A. Dwivedi, “Comparative Study of Molecular Docking, Structural, Electronic, Vibrational Spectra and Fukui Function Studies of Thiadiazole Containing Schiff Base – A Complete Density Functional Study,” Polycyclic Aromatic Compounds 42, no. 1 (2022): 13–39.
   Web of Science ®Google Scholar
• S. Lahmidi, Y. Sert, F. Şen, M. El Hafi, W. Ettahiri, H. Gökce, E.M. Essassi, J.T. Mague, and F. Ucun, “Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Spectral Characterizations and Quantum Computational Assessments of 1-Hydroxy-3-Methyl-11H-Pyrido[2,1-b] Quinazolin-11-One,” Journal of Molecular Structure 1249 (2022): 131592.
   Web of Science ®Google Scholar
• N. Dege, H. Gökce, O. E. Doğan, G. Alpaslan, T. Ağar, S. Muthu, and Y. Sert, “Quantum computational, spectroscopic investigations on N-(2-((2-chloro-4,5-dicyanophenyl)amino)ethyl)-4-methylbenzenesulfonamide by DFT/TD-DFT with different solvents, molecular docking and drug-likeness researches,” Colloids and Surfaces A: Physicochemical and Engineering Aspects 638 (2022): 128311.
   Web of Science ®Google Scholar
• A.A. Abdulridha, M.A. Albo Hay Allah, S.Q. Makki, Y. Sert, H. Edan Salman, and A.A. Balakit, “Corrosion inhibition of carbon steel in 1 M H2SO4 using new Azo Schiff compound: Electrochemical, gravimetric, adsorption, surface and DFT studies,” Journal of Molecular Liquids 315 (2020): 113690.
   Web of Science ®Google Scholar
• M.A. Albo Hay Allah, A.A. Balakit, H. Idan Salman, A.A. Abdulridha, and Y. Sert, “New Heterocyclic Compound as Carbon Steel Corrosion Inhibitor in 1 M H2SO4, High Efficiency at Low Concentration: Experimental and Theoretical Studies”, Journal of Adhesion Science and Technology (2022). doi:10.1080/01694243.2022.2034588.
   Google Scholar
• W. Al Garadi, Y. Sert, M. El Hafi, B. El Ibrahimi, Y. Ramli, J.T. Mague, L. El Ghayati, N.K. Sebbar, and E.M. Essassi, “One‐Step Synthesis of Novel N1‐Substituted Benzimidazole Derivatives: Experimental and Theoretical Investigations”, Journal of Heterocyclic Chemistry 59, no. 7 (2022): 1213-1229. doi:10.1002/jhet.4461
   Google Scholar
• G.M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica. Section A, Foundations of Crystallography 64, no. Pt 1 (2008): 112–22.
   PubMedGoogle Scholar
• G.M. Sheldrick, SHELXL2014, a program for crystal structure refinement (Germany: University of Gottingen, 2015).
   Google Scholar
• L.J. Farrugia, “WinGX Suite for Small-Molecule Single-Crystal Crystallography,” Journal of Applied Crystallography 32, no. 4 (1999): 837–8.
   Google Scholar
• P.J. Brown, A.G. Fox, E.N. Maslen, M.A. O'Keefe, and B.T.M. Willis, “International Tables for-ray Crystallography,” in edited by A.J.C. Wilson and E. Prince, Vol. C (Dordrecht: Kluwer Academic Publishers, 1999), 548–589.
   Google Scholar
• R.F. Stewart, E.R. Davidson, and W.T. Simpson, “Coherent X-Ray Scattering for the Hydrogen Atom in the Hydrogen Molecule,” The Journal of Chemical Physics 42, no. 9 (1965): 3175–87.
   Web of Science ®Google Scholar
• M.J. Frisch, J.A. Pople, and J.S. Binkley, “Self‐Consistent Molecular Orbital Methods 25. Supplementary Functions for Gaussian Basis Sets,” The Journal of Chemical Physics 80, no. 7 (1984): 3265–9.
   Web of Science ®Google Scholar
• M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, et al, Gaussian 09 (Wallingford, CT: Gaussian Inc., 2009).
   Google Scholar
• R. Dennington, T. Keith, and J. Millam, GaussView, Version 5 (Shawnee Mission, KS: SemichemInc., 2009).
   Google Scholar
• M.H. Jamróz, “Vibrational Energy Distribution Analysis (VEDA): Scopes and Limitations,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 114 (2013): 220–30.
   PubMed Web of Science ®Google Scholar
• J.B. Foresman and A. Frisch, “Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian”, 2nd ed (Pittsburgh: Gaussian, 1996).
   Google Scholar
• D. Avcı, and Y. Atalay, “Effects of Different GIAO and CSGT Models and Basis Sets on 2-Aryl-1,3,4-Oxadiazole Derivatives,” Structural Chemistry 20, no. 2 (2009): 185–201.
   Web of Science ®Google Scholar
• N. Boukabcha, A. Djafri, Y. Megrouss, Ö. Tamer, D. Avcı, M. Tuna, N. Dege, A. Chouaih, Y. Atalay, A. Djafri, et al, “Synthesis, Crystal Structure, Spectroscopic Characterization and Nonlinear Optical Properties of (Z)-N’-(2,4- Dinitrobenzylidene)-2-(Quinolin-8-Yloxy) Acetohydrazide,” Journal of Molecular Structure 1194 (2019): 112–23.
   Web of Science ®Google Scholar
• S. Yahiaoui, A. Moliterni, N. Corriero, C. Cuocci, K. Toubal, A. Chouaih, A. Djafri, and F. Hamzaoui, “2-thioxo- 3N-(2-Methoxyphenyl) −5 [4′-Methyl -3′N -(2′-Methoxyphenyl) Thiazol-2′(3′H)-Ylidene] Thiazolidin-4-One: Synthesis, Characterization, X-Ray Single Crystal Structure Investigation and Quantum Chemical Calculations,” Journal of Molecular Structure 1177 (2019): 186–92.
   Web of Science ®Google Scholar
• N. Benhalima, K. Toubal, A. Chouaih, G. Chita, S. Maggi, A. Djafri, and F. Hamzaoui, “Synthesis and Molecular Structure Investigation by DFT and x-Ray Diffraction of ARNO,” Journal of Chemical Crystallography 41, no. 11 (2011): 1729–36.
   Web of Science ®Google Scholar
• N. Khelloul, K. Toubal, N. Benhalima, R. Rahmani, A. Chouaih, A. Djafri, and F. Hamzaoui, “Crystal Structure, Hirshfeld Surface Analysis and Computational Studies of Thiazolidin-4-One Derivative: (Z)-5-(4-Chlorobenzylidene)-3-(2-Ethoxyphenyl) -2-Thioxothiazolidin-4-One,” Acta Chimica Slovenica 63, no. 3 (2016): 619–26.
   PubMed Web of Science ®Google Scholar
• M. Boulakoud, K. Toubal, S. Yahiaoui, A. Chouaih, G. Chita, A. Djafri, and F. Hamzaoui, “Molecular Structure Investigation of z-3n(2-Ethoxyphenyl)-2-n′(2-Ethoxyphenyl)-Imino-Thiazolidin-4-One by ab Initio, DFT and x-Ray Diffraction Methods,” Journal of Structural Chemistry 56, no. 7 (2015): 1373–8.
   Web of Science ®Google Scholar
• F.L. Hirshfeld, “Synthesis, Crystal Structure, and Hirshfeld Surface Analysis of a New Mixed Ligand Copper(II) Complex,” Theoretica Chimica Acta 44, no. 2 (1977): 129–38.
   Google Scholar
• H.F. Clausen, M.S. Chevallier, M.A. Spackman, and B.B. Iversen, “Three New co-Crystals of Hydroquinone: crystal Structures and Hirshfeld Surface Analysis of Intermolecular Interactions,” New Journal of Chemistry 34, no. 2 (2010): 193–9.
   Web of Science ®Google Scholar
• M.A. Spackman and J.J. McKinnon, “Fingerprinting Intermolecular Interactions in Molecular Crystals,” CrystEngComm 4, no. 66 (2002): 378–92.
   Google Scholar
• A.L. Rohl, M. Moret, W. Kaminsky, K. Claborn, J.J. McKinnon, and B. Kahr, “Hirshfeld Surfaces Identify Inadequacies in Computation of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone,” Crystal Growth & Design 8, no. 12 (2008): 4517–25.
   Web of Science ®Google Scholar
• M.A. Spackman and D. Jayatilaka, “Hirshfeld Surface Analysis,” CrystEngComm 11, no. 1 (2009): 19–32.
   Web of Science ®Google Scholar
• N. Boukabcha, A. Direm, M. Drissi, Y. Megrouss, N. Khelloul, N. Dege, M. Tuna, and A. Chouaih, “Synthesis, Structural Determination, Hirshfeld Surface Analysis, 3D Energy Frameworks, Electronic and (Static, Dynamic) NLO Properties of o-Nitroacetanilide (o-NAA): a Combined Experimental and Quantum Chemical Study,” Inorganic Chemistry Communications 133 (2021): 108884.
   Web of Science ®Google Scholar
• V.K. Kumar, S. Dheivamalar, R.J. Xavier, and V. Balachandran, “Analysis of Vibrational Spectra of 4-Amino-2,6-Dichloropyridine and 2-Chloro-3,5-Dinitropyridine Based on Density Functional Theory Calculations,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 65, no. 1 (2006): 147–54.
   PubMed Web of Science ®Google Scholar
• M. Ramalingam, V. Sethuraman, and N. Sundaraganesan, “Molecular Structure, Vibrational Spectroscopic, First Order Hyperpolarizability and HOMO-LUMO Studies of 7-Amino-8-Oxo-3-Vinyl-5-Thia-1-Azabicyclo[4.2.0,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 78, no. 2 (2011): 660–9.
   PubMed Web of Science ®Google Scholar
• R.M. Silverstein and F.X. Webster, Spectrometric Identification of Organic Compounds (New York: Jon Wiley Sons Inc., 1963), 72.
   Google Scholar
• J.B. Lambert, H.F. Shurvell, L. Verbit, R.G. Cooker, and G.H. Stout, Organic Structural Analysis (New York: Macmillan, 1976).
   Google Scholar
• R.N. Singh, A. Kumar, P. Rawat, R.K. Tiwari, and A.K. Singh, “Studies on Molecular Structure. Spectral Analysis. Chemical Reactivity and First Hyperpolarizability of a Newly Synthesized 1,9-Bis[(4-Isonicotinoyl)-Hydrazonomethyl]-5-Phenyl-Dipyrromethane Using Experimental and Theoretical Approaches,” Journal of Molecular Structure 1052 (2013): 67–75.
   Web of Science ®Google Scholar
• G. Socrates, Infrared Characteristic Group Frequencies (Chichester: Wiley-Interscience, 1980).
   Google Scholar
• G. Varsányi, Vibrational Spectra of Benzene Derivatives (Burlington: Elsevier, 2012).
   Google Scholar
• N. Subramanian, N. Sundaraganesan, and J. Jayabharathi, “Molecular Structure, Spectroscopic (FT-IR, FT-Raman, NMR, UV) Studies and First-Order Molecular Hyperpolarizabilities of 1, 2-Bis (3-Methoxy-4-Hydroxybenzylidene) Hydrazine by Density Functional Method,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 76, no. 2 (2010): 259–69.
   PubMed Web of Science ®Google Scholar
• E. Scrocco and J. Tomasi, “Electronic Molecular Structure, Reactivity and Intermolecular Forces: An Euristic Interpretation by Means of Electrostatic Molecular Potentials,” Advances in Quantum Chemistry 11 (1979): 115–193. doi: 10.1016/S0065-3276(08)60236-1
   Google Scholar
• F.J. Luque, J.M. Lopez, and M. Orozco, “Perspective on Electrostatic Interactions of a Solute with a Continuum. A Direct Utilization of ab Initio Molecular Potentials for the Prevision of Solvent Effects,” Theoretical Chemistry Accounts 103, no. 3–4 (2000): 343–5.
   Web of Science ®Google Scholar
• T. Yanai, D.P. Tew, and N.C. Handy, “A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP),” Chemical Physics Letters. 393, no. 1–3 (2004): 51–7.
   Web of Science ®Google Scholar
• S. Armaković and S.J. Armaković, “Atomistica.online – Web Application for Generating Input Files for ORCA Molecular Modelling Package Made with the Anvil Platform,” Molecular Simulation (2022): 1–7.
   Web of Science ®Google Scholar
• Y. Megrouss, F. Triki-Baara, N. Boukabcha, A. Chouaih, A. Hatzidimitriou, A. Djafri, and F. Hamzaoui, “Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method,” Acta Chimica Slovenica 66, no. 2 (2019): 490–500.
   PubMed Web of Science ®Google Scholar
• N.E.H. Belkafouf, F. Triki-Baara, A. Altomare, R. Rizzi, A. Chouaih, A. Djafri, and F. Hamzaoui, “Synthesis, PXRD Structural Determination, Hirshfeld Surface Analysis, and DFT/TD-DFT Investigation of 3N-Ethyl-2N’-(2-Ethylphenylimino) Thiazolidin-4-One,” Journal of Molecular Structure 1189 (2019): 8–20.
   Web of Science ®Google Scholar
• H.P. Gümü, S.Ö. Tamer, D. Avcı, and Y. Atalay, “Quantum Chemical Calculations on the Geometrical, Conformational, Spectroscopic and Nonlinear Optical Parameters of 5-(2-Chloroethyl)-2,4-Dichloro-6-Methylpyrimidine,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 129 (2014): 219–26.
   PubMed Web of Science ®Google Scholar
• H. Bennaissi, M. Drissi, S. Yahiaoui, Y. Megrouss, A. Chouaih, and F. Hamzaoui, “Hirshfeld Surface Analysis, Topological Features and Nonlinear Optical Properties of Phthalonitrile Derivative: low Temperature Experimental Charge Density and Quantum Chemistry Studies,” Journal of Optoelectronics and Biomedical Materials 10, no. 3 (2018): 73–82.
   Web of Science ®Google Scholar
• V.M. Geskin, C. Lambert, and J.L. Bredas, “Origin of High Second- and Third-Order Nonlinear Optical Response in Ammonio/Boratodiphenylpolyene Zwitterions: The Remarkable Role of Polarized Aromatic Groups,” Journal of the American Chemical Society 125, no. 50 (2003): 15651–8.
   PubMed Web of Science ®Google Scholar
• R. Zhang, B. Du, G. Sun, and Y. Sun, “Experimental and Theoretical Studies on o-, m-and p-Chlorobenzylideneaminoantipyrines,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 75, no. 3 (2010): 1115–24.
   PubMed Web of Science ®Google Scholar
• E. Scrocco and J. Tomasi, “Electronic Molecular Structure, reactivity and intermolecular Forces: An Heuristic Interpretation by Means of Electrostatic Molecular Potentials,” Advances in Quantum Chemistry 11 (1978): 115–93.
   Google Scholar
• R. Rahmani, N. Boukabcha, A. Chouaih, F. Hamzaoui, and S. Goumri-Said, “On the Molecular Structure, Vibrational Spectra, HOMO-LUMO, Molecular Electrostatic Potential, UV-Vis, First Order Hyperpolarizability, and Thermodynamic Investigations of 3-(4-Chlorophenyl)-1-(1yridine-3-yl) Prop-2-en-1-One by Quantum Chemistry Calculations,” Journal of Molecular Structure 1155 (2018): 484–95.
   Web of Science ®Google Scholar
• D. A. Kleinman, “Nonlinear Dielectric Polarization in Optical Media,” Physical Review 126, no. 6 (1962): 1977–9.
   Web of Science ®Google Scholar
• T. Abbaz, A. Bendjeddou, and D. Villemin, “Theoretical Investigations on Molecular Structure, HOMO, LUMO, NBO Analysis and Hyperpolarizability Calculations of Mono and Extended-Tetrathiafulvalenes,” Indo American Journal of Pharmaceutical Science 5, no. 04 (2018): 2488–98.
   Google Scholar
• E. Gobinath, and R. J. Xavier, “Quantum Chemical Calculations, Vibrational Studies, HOMO-LUMO and NBO/NLMO Analysis of 2-Bromo-5-Nitrothiazole,” Spectrochimica Acta–Part A, Molecular and Biomolecular Spectroscopy 104 (2013): 394–402.
   PubMed Web of Science ®Google Scholar