Combined Experimental and Computational Investigation of 2-(2-Hydroxyphenylimino) Phenolic Derivatives: Synthesis, Molecular Structure and NLO Studies — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Combined Experimental and Computational Investigation of 2-(2-Hydroxyphenylimino) Phenolic Derivatives: Synthesis, Molecular Structure and NLO Studies
Research Department of Physics, Kongunadu Arts and Science College (Autonomous), Coimbatore, India
,
Research Department of Physics, Government Arts College (Autonomous), Coimbatore, India
1 Research Department of Physics, Kongunadu Arts and Science College (Autonomous), Coimbatore, India
2 Research Department of Physics, Government Arts College (Autonomous), Coimbatore, India
A series of substituted 2-(2-hydroxyphenylimino) phenolic ( salen ) derivatives (1-4) have been synthesized and their structures of obtained compound were characterized by analytical, FT-IR, UV-Vis and 13 C{ 1 H}-NMR experimentally. The geometry structure optimization, frequencies (IR), NMR, electronic character, frontier molecular orbital (HOMO-LUMO) and first static hyperpolarizability ( β tot ) studies of reported compounds were calculated using DFT with B3LYP/6-311G(d,p) level of theory. The calculated HOMO and LUMO energies showed that charge transfer occurs within the molecule and from the MEP, the molecular stability and bond strength have been explained. In addition to that influence of energy gap (?E gap ) between the HOMO-LUMO orbitals on the first static hyperpolarizability (β tot ), we calculated the ?E gap for all the salen compounds. These results reveals that the smaller HOMO-LUMO ?E gap is, larger the β tot is.
Ayman, A., Aziz, A., Salem, M.A.N., Sayed, M.A. and Aboaly, M.M. (2012) Synthesis, Structural Characterization, Thermal Studies, Catalytic Efficiency and Antimicrobial Activity of Some M(II) Complexes with ONO TRIDENTATE SCHIFF BASE N-Salicylidene-o-Aminophenol (saphH2). Journal of Molecular Structure, 1010, 130-138.
Opstal, T. and Verpoort, F. (2003) Synthesis of Highly Active Ruthenium Indenylidene Complexes for Atom-Transfer Radical Polymerization and Ring-Opening- Metathesis Polymerization. Angewandte Chemie International Edition, 42, 2876-2886. https://doi.org/10.1002/anie.200250840
da Silva, C.M., da Silva, D.L., Modolo, L.V., Alves, R.B., Martins, C.V.B., de Resende, M.A. and de Fátima, A. (2011) Schiff Bases: A Short Review of Their Antimicrobial Activities. Journal of Advanced Research, 2, 1-8.
Sztanke, K., Maziarka, A., Osinka, A. and Sztanke, M. (2013) An Insight into Synthetic Schiff Bases Revealing Antiproliferative Activities in Vitro. Bioorganic & Medicinal Chemistry, 21, 3648-3666.
Hameed, A., Al-Rashida, M., Uroos, M., Ali, S.A. and Khan, K.M. (2017) Schiff Bases in Medicinal Chemistry: A Patent Review (2010-2015). Expert Opinion on Therapeutic Patents, 27, 63-79. https://doi.org/10.1080/13543776.2017.1252752
Sirajuddin, M., Uddin, N., Ali, S. and Tahir, M.N. (2013) Potential Bioactive Schiff Base Compounds: Synthesis, Characterization, X-Ray Structures, Biological Screenings and Interaction with Salmon Sperm DNA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 116, 111-121.
Govindarasu, K. and Kavitha, E. (2014) Vibrational Spectra, Molecular Structure, NBO, NMR, UV, First Order Hyperpolarizability, Analysis of (S)-(-)-N-(5-Nitro-2- Pyridyl) Alaninol by Density Functional Theory. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 127, 498-510.
Chandra, S. and Saneetika, X. (2004) EPR, Magnetic and Spectral Studies of Copper(II) and Nickel(II) Complexes of Schiff Base Macrocyclic Ligand Derived from Thiosemicarbazide and Glyoxal. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 60, 147-153.
Finkel, T. and Holbrook, N.J. (2000) Review Article Oxidants, Oxidative Stress and the Biology of Ageing. Nature, 408, 239-247. https://doi.org/10.1038/35041687
Zhou, L., Cai, P., Feng, Y., Cheng, J., Xiang, H., Liu, J., Wu, D. and Zhou, X. (2012) Synthesis and Photophysical Properties of Water-Soluble Sulfonato-Salen-Type Schiff Bases and Their Applications of Fluorescence Sensors for Cu2+ in Water and Living Cells. Analytica Chimica Acta, 735, 96-106.
Priyarega, S., Prabhakaran, R., Aranganayagam, K.R., Karvembu, R. and Natarajan, K. (2007) Synthetic and Catalytic Investigations of Ruthenium(III) Complexes with Triphenylphosphine/Triphenylarsine and Tridentate Schiff Base. Applied Organometallic Chemistry, 21, 788-793. https://doi.org/10.1002/aoc.1281
Mazzi, U., Refosco, F., Tisato, F., Bandoli, G. and Nicolini, M. (1986) Mixed Tri- and Bi-Dentate Schiff-Base Complexes of Technetium(V) and Rhenium(V). The Crystal Structure of N-(2-Oxidophenyl)Salicylideneiminato-NOO’)Oxo(8-Quino-linolato-NO)Technetium(V). Journal of the Chemical Society, Dalton Transactions, No. 8, 1623-1628. https://doi.org/10.1039/DT9860001623
Tisato, F., Refosco, F., Mazzi, U., Bandolin, U. and Nicolini, M. (1987) Technetium(V) and Rhenium(V) Complexes with N-(2-Mercaptophenyl)Salicylideneiminate. Crystal Structure of Chlo-ro(oxo)[N-(2-Sulphidophenyl)Salicylideneiminato-NOS]Technetium(V). Journal of the Chemical Society, Dalton Transactions, No. 7, 1693-1699. https://doi.org/10.1039/dt9870001693
Priyarega, S., Tamizh, M.M., Karvembu, R., Prab-hakaran, R. and Natarajan, K. (2011) Synthesis, Spectroscopic Characterization and Catalytic Oxidation Properties of ONO/ONS Donor Schiff Base Ruthenium(III) Complexes Containing PPh3/ AsPh3. Journal of Chemical Sciences, 123, 319-325. https://doi.org/10.1007/s12039-011-0087-2
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery Jr., J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A, Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Reploge, E.S. and Pople, J.A. (2005) Gaussian 03, Revision D.01. Gaussian, Inc., Pittsburgh, PA.
Kohn, W. (1999) Nobel Lecture: Elec-tronic Structure of Matter—Wave Functions and Density Functionals. Reviews of Modern Physics, 71, 1253. https://doi.org/10.1103/RevModPhys.71.1253
Becke, A.D. (1998) Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Physical Review A, 38, 3098. https://doi.org/10.1103/PhysRevA.38.3098
Lee, C., Yang, W. and Parr, R.G. (1988) Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Physical Review B, 37, 785. https://doi.org/10.1103/PhysRevB.37.785
Frisch, M.J., Pople, J.A. and Binkley, J.S. (1984) Self-Consistent Molecular Orbital Methods 25. Supplementary Functions for Gaussian Basis Sets. The Journal of Chemical Physics, 80, 3265. https://doi.org/10.1063/1.447079
Hehre, W.J., Radom, L., Schleyer, P.V.R. and Pople, J.A. (1986) Ab Initio Molecular Orbital Theory. Wiley, New York.
Kohn, W., Becke, A.D. and Parr, R.G. (1996) Density Functional Theory of Electronic Structure. The Journal of Physical Chemistry, 100, 12974-12980. https://doi.org/10.1021/jp960669l
Parr, R.G. and Pearson, R.G. (1983) Absolute Hardness: Companion Parameter to Absolute Electronegativity. Journal of the American Chemical Society, 105, 7512-7516. https://doi.org/10.1021/ja00364a005
Parr, R.G., Szentpaly, L.V. and Liu, S. (1999) Electrophilicity Index. Journal of the American Chemical Society, 121, 1922-1924. https://doi.org/10.1021/ja983494x
Chattaraj, P.K., Lee, H. and Parr, R.G. (1991) HSAB Principle. Journal of the American Chemical Society, 113, 1855-1856. https://doi.org/10.1021/ja00005a073
Sadasivam, K. and Kumaresan, R. (2011) Antioxidant Behavior of Mearnsetin and Myricetin Flavonoid Compounds—A DFT Study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79, 282-293.
Gabr, A.A. (1990) Spectrophotometric Studies on Some Schiff Bases deriveD from Benzidine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 46, 1751-1757.
Wright, J.S., Johnson, E.R. and Dilabio, G.A (2001) Predicting the Activity of Phenolic Antioxidants: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants. Journal of the American Chemical Society, 123, 1173-1183. https://doi.org/10.1021/ja002455u
Sadasivam, K. and Kumaresan, R. (2011) Theoretical Investigation on the Antioxidant Behavior of Chrysoeriol and Hispidulin Flavonoid Compounds—A DFT Study. Computational and Theoretical Chemistry, 963, 227-235.
Politzer, P. and Truhlar, D.G., Eds. (1981) Plenum, New York.
Pipek, J. and Mezey, P.Z. (1989) A Fast Intrinsic Localization Procedure Applicable for ab Initio and Semiempirical Linear Combination of Atomic Orbital Wave Functions. The Journal of Chemical Physics, 90, 4916. https://doi.org/10.1063/1.456588
Wang, P., Zhu, P., Wang, C. and Ye, C. (1999) Theoretical Investigation and Molecular Design of Pyrazine Derivatives with Large Hyperpolarizabilities (β). Journal of Molecular Structure: THEOCHEM, 459, 155-162.
Tang, G.D., Jiang, Z.J., Li, R.Q., Zhang, J.F., Zhang, Y. and Zhang, C. (2009) DFT Studies on Nonlinear Optical Properties of Neutral Nest-Shaped Heterothiometallic [MOS3Py5Cu3X] (M = Mo, W; X = F, Cl, Br, I) Clusters. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74, 228-232.