Synthesis, crystal structure, spectroscopic, molecular docking and DFT Studies of two Schiff base ligands derived from DL-1- Phenylethylamine

Document Type : Original Article

Authors

1 Department of chemistry, Semnan University, Semnan,iran

2 Faculty of Chemistry, Adam Mickiewicz University, Poznan, Poland

Abstract

In the present work a new Schiff base ligand was prepared by condensation of 4-hydroxy-3-methoxybenzaldehyde with DL-1-phenylethylamine (HL1). The product was characterized using FT-IR, 1H-NMR, and UV-Vis spectroscopy. The structure of HL1 Schiff base ligand was determined by X-ray crystallography. According to this analysis, HL1 ligand is crystallized in the orthorhombic crystal structure with space group Pbca. Also, the structure and electronic properties of HL2 Schiff base ligand which was synthesized before and HL1 ligand were analyzed by using DFT calculations. The docking analysis of ligands was reported that bind to the minor and major grooves of B-DNA sequence, respectively.

Keywords

Main Subjects

References

[1] Zh. Yang, L. Wang, Zh. Zhou, Q. Zhou, Ch. Tang, Tetrahedron: Asymmetry, 12 (2001) 1579.
[2] K.C. Emregul, E. Duzgun, O. Atakol, Corrosion Science, 48 (2006) 3243.
[3] A. Prakash, D. Adhikari, Int. J. ChemTech Res. 3 (2011) 1891.
[4] K. Bhat, K.J. Chang, M.D. Aggarwal, W.S. Wang, B.G. Penn, D.O. Frazier, Materials Chemistry and Physics, 44 ( 1996) 261.
[5] M.P. Akerman, V.A. Chiazzari, J. Mol. Struct. 1058 (2014) 22.
[6] R.M. Issa, M. K. Awad, F.M. Atlam, Materials and Corrosion, 61 (2010) 709-714.
[7] Z. Parsaee, J. Mol. Struct. 1146 (2017) 644.
[8] S. Grimme, Journal of Computational Chemistry, 25 (2004) 1463.
[9] Q.T. That, K. Nguyen, P. Hansen, Magnetic Resonance in Chemistry, 43 (2005) 302.
[10] S. Sinnecker, L.D. Slep, E. Bill, F. Neese, Inorg. Chem. 44 (2005) 2245.
[11] S.D. George, T. Petrenko, F. Neese, Inorg. Chim. Acta, 361 (2008) 965.
[12] K. Ray, S.D.George, E.I. Solomon, K. Wieghardt, F. Neese, Chem. Eur. J. 13( 2007) 2783.
[13] S. Basak, D. Chopra, K.K. Rajak, Journal of Organometallic Chemistry, 693 (2008) 2649.
[14] M. Seth, T. Ziegler, J. Chem. Phys. 120 (2004) 10942.
[15] P. AdAo, J. Pessoa, R.T. Henriques, M.L. Kuznetsov, F. Avecilla, M.R. Maurya, U. Kumar, I. Correia, Inorg. Chem. 48 (2009) 3542.
[16] Z. Parsaee, Kh. Mohammadi, J. Mol. Struct. 1137 (2017) 512.
[17] C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins, A. de Fatima, Journal of Advanced Research, 2 (2011) 1.
[18] L. Shi, H. Ge, Sh. Tan, H. Li, Y. Song, H. Zhu, R. Tan, European Journal of Medicinal Chemistry, 42 (2007) 558.
[19] B.S. Creaven, B. Duff, D.A. Egan, K. Kavanagh, G. Rosair, V.R. Thangella, M. Walsh, Inorg. Chim. Acta, 363 (2010) 4048.
[20] G. Ceyhan, M. Kose, M. Tumer, I. Demirtas, A. Yaglioglu, V. McKee, Journal of Luminescence, 143 (2013) 623.
[21] K. Das, A. Datta, P. Liu, J. Huang, Ch. Hsu, W. Chang, B. Machura, Ch. Sinha, Polyhedron, 71 (2014) 85.
[22] A.A. El-Sherif, T.M.A. Eldebss, Spectrochim. Acta, Part A, 79 (2011) 1803.
[23] Sh.M. Sondhi, N. Singh, A. Kumar, O. Lozachc, L. Meijer, Bioorganic & Medicinal Chemistry, 14 (2006) 3758.
[24] Z. Abbasi, M. Salehi, M. Kubicki, A. Khaleghian, J. Coord. Chem. 70 (2017) 2074.
[25] R. Fekri, M. Salehi, A. Asadi, M. Kubicki, Polyhedron, 128 (2017) 175.
[26] H.-L. ZHU, X. -Y. LIU, Synth. React. Inorg. Met. Org. Chem. 35 (2005) 193.
[27] Jaworska, M., Wełniak, M., Zięciak, J., Kozakiewicz, A., Wojtczakb, A." Arkivoc 9 (2011) 189.
[28]  CrysAlisPro 1.171.38.34a (Rigaku OD, 2015).
[29] A. Altomare, G. Cascarano, C. Giacovazzo and A. Gualardi, J. Appl. Crystallogr. 26 (1993), 343.
[30] G. M. Sheldrick, Acta Crystallogr., 2014, C71, 3.
[31] M.J. Frisch, et al., Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.
[32] J. B. Foresman, A. Frisch, Exploring Chemistry with Electronic Structure Meth Ods, 2nd ed., Gaussian Inc., Pittsburgh, PA, 1996.
[33] E.D. Glendening, A.E. Reed, J. E. Carpenter, F. Weinhold, NBO Version 3.1 TCI,
University of Wisconsin, Madison, 65 (1998).
[34] N.S. Biradar, V.H. Kulkami, J. Inorg. Nucl. Chem. 33 (1971) 3781.
[35] J. N.R. Ruddick, J. R. Sams, J. Organomet. Chem. 60 (1973) 233.
[36] C. Cappelli, C. Duce, M. Formica, V. Fusi, L. Ghezzi, L. Giorgi, M. Micheloni, P. Paoli,
P. Rossi, M. Rosaria Tine, Inorg. Chim. Acta. 417 (2014) 230.
[37] M. Amini, M. Khaksar, A. Arab, R. Masoomi Jahandizi, M. Bagherzadeh, D.M. Boghaei, A. Ellern, L.K. Woo, Transition. Met. Chem. 41 (2016) 97.
[38] A. Arab, F. Gobal, N. Nahali, M. Nahali, J. Clust. Sci. 24 (2013) 273.
[39] A. Arab, M. Habibzadeh, Comput. Theor. Chem. 1068 (2015) 52.
[40] F. Arjmand, Sh. Parveen, M..Afzal, M. Shahid,, J. Photochem. Photobiol. 114 (3) (2012) 15.
Applied Chemistry Today
Volume 13, Issue 49
December 2018
Pages 103-116

Files

Share

How to cite

Statistics