European Journal of Chemistry 2014, 5(2), 343-350. doi:10.5155/eurjchem.5.2.343-350.959

Ab initio calculations of 13C NMR chemical shielding in some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety

Majid Rezaeivala (1,*) , Sam Daftari (2)

(1) Department of Chemical Engineering, Hamedan University of Technology, Hamedan 65157, Iran
(2) Department of Environmental Sciences, University of Omran and Toseeh, Hamedan, 65157, Iran
(*) Corresponding Author

Received: 27 Oct 2013, Accepted: 04 Feb 2014, Published: 30 Jun 2014


The calculation of 13C isotropic shielding constants by means of GIAO and CSGT methods of eight Schiff base ligands containing piperazine moiety at the Hartree-Fock and B3LYP levels of theory are presented. Good linear correlations between the calculated chemical shielding at gas-phase and experimental shift values in CDCl3 solution were obtained. Density functional theory (DFT) calculations at the B3LYP/6-31G(2d,p) level of theory is used to optimize the geometry of ligands. Calculated nuclear magnetic resonance (NMR) chemical shifts 13C are reported for the some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety. In order to establish a convenient and consistent protocol to be employed for confirming the experimental 13C NMR spectra of Schiff base ligands, different combinations of models and basis sets were considered. The most reliable results were obtained at B3LYP/6-311G++ (d,p) level and CSGT method which can be used to predict 13C NMR chemical shifts with a very high accuracy for latter compounds. These results show the agreement between theoretical and experimental 13C NMR chemical shielding of mentioned ligands.


DFT; GIAO; CSGT; Ab initio; Schiff base; Piperazine

Full Text:

PDF /    /

DOI: 10.5155/eurjchem.5.2.343-350.959

Article Metrics

This Abstract was viewed 665 times | PDF Article downloaded 192 times



[1]. M. Rezaeivala, R. Golbedaghi, M. Khalili
Coordination chemistry of some new Cu(II), Ni(II) and Co(II) macroacyclic (N2O4) Schiff base complexes: X-ray crystal structure of Cu(II) complex
Russian Journal of Coordination Chemistry  42(1), 66, 2016
DOI: 10.1134/S1070328415120064


[1]. Gauss, J.; Bunsen-Ges, B. Phys. Chem. 1995, 99, 1001-1008.

[2]. Ziegler, T. Chem. Rev. 1991, 91, 651-667.

[3]. Hohenberg, P.; Kohn, W. Phys. Rev. B. 1964, 136, 864-871.

[4]. Vignale, G.; Rasolt, M.; Geldard, D. J. W. Adv. Quant. Chem. 1990, 21, 235-253.

[5]. Lee, A. M.; Handy, N. C.; Colwell, S. M. J. Chem. Phys. 1995, 103, 10095-10109.

[6]. Ando, I.; Webb, G. A. Theory of NMR Parameters, Academic Press, London, 1983.

[7]. Facelli, J. C.; Hu, J. Z.; Orendt, A. M.; Arif, A. M.; Pugmire, R. J.; Grant, D. M. J. Phys. Chem. 1994, 98, 12186-12190.

[8]. Zheng, G.; Hu, J.; Zhang, X.; Shen, L.; Yea, C.; Webb, G. A. J. Mol. Struct. (Theochem) 1998, 428, 283-286.

[9]. Bagno, A.; Rastrelli, F.; Saielli, G. Chem. Eur. J. 2006, 12, 5514-5525.

[10]. Price, W. S.; Hwamg, J. L. P. J. Chin. Chem. Soc. 1992, 39, 497-507.

[11]. Jiang, B. C.; Miao, X. J.; Hwang, L. P.; Ye, C. H. J. Chin. Chem. Soc. 1995, 42, 887-892.

[12]. Borisova, N. E.; Reshetova, M. D.; Ustynyuk, Y. A. Chem. Rev. 2007, 107, 46-79.

[13]. Vigato, P. A.; Tamburini, S.; Bertolo, L. Coord. Chem. Rev. 2007, 251, 1311-1620.

[14]. Beckmann, U.; Brooker, S. Coord. Chem. Rev. 2003, 245, 17-29.

[15]. Radecka-Paryzek, W.; Patroniak, V.; Lisowski, J. Coord. Chem. Rev. 2005, 249, 2156-2175.

[16]. Bouwman, E.; Reedijk, J. Coord. Chem. Rev. 2005, 249, 1555-1581.

[17]. Vigato, P. A.; Tamburini, S. Coord. Chem. Rev. 2008, 252, 1871-2154.

[18]. Okawa, H.; Furutachi, H.; Fenton, D. E. Coord. Chem. Rev. 1998, 174, 51-75.

[19]. Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410-421.

[20]. Grigoropoulou, G.; Clark, J. H.; Elings, J. A. Green Chem. 2003, 5, 1-7.

[21]. Sheldon, R. A.; Kochi, J. K. In Metal-catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.

[22]. Hudlicky, M. In Oxidation in Organic Chemistry, ACS Monographs 186. Washington, DC, 1990.

[23]. Ditchfield, R. Mol. Phys. 1974, 27, 789-807.

[24]. Keith, T.; Bader, R. Chem. Phys. Lett. 1993, 179, 479-482.

[25]. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.

[26]. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1-8.

[27]. Keith, T. A, Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223-231.

[28]. Prakash, R. V.; Rasul, G.; Surya, P. G. K.; Olah, G. A. J. Org. Chem. 2003, 68, 3507-3510.

[29]. Katritzky, A. R.; Akhmedov, N. G.; Güven, A.; Doskocz, J.; Akhmedova, R. G.; Majumder, S.; Dennis Hall, C. J. Mol. Struct. 2006, 787, 131-147.

[30]. Meng, Z.; Carper, W. R. J. Mol. Struct. (Theochem.) 2002, 588, 45-53.

[31]. Gallant, A. J.; Hui, J. K. H.; Zahariev, F. E.; Wang, Y. A.; MacLachlan, M. J. J. Org. Chem. 2005, 70, 7936-7946.

[32]. Salehzadeh, S.; Bayat, M. J. Chinese Chem. Soc. 2007, 54, 1145-1150.

[33]. Khanmohammadi, H.; Erfantalab, M. Spectrochim. Acta A 2010, 75, 127-133.

[34]. Sheikhshoaie, I.; Saheb, V. Spectrochim. Acta A 2010, 77, 1069-1076.

[35]. Infante-Castillo, R. J. Mol. Struct. (Theochem) 2010, 940, 124-128.

[36]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.

[37]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, 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.; Menucci, 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.; Ciolowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Jonhson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Repogle, E. S.; Pople, J. A., Gaussian 03, Gaussian Inc., 2003, Pittsburgh, PA, USA.

[38]. Cheeseman, J. R. Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509.

[39]. Hyper Chem. Released on May 2nd; Hypercube, INC: Gainesville 1997.

[40]. Keypour, H.; Rezaeivala, M.; Fall, Y.; Dehghani-Firouzabadi, A. A. Arkivoc 2009, 10, 292-301.

[41]. Larkins, H. L.; Hamilton, A. D. Tetrahedron Lett. 1986, 27, 2721-2724.

[42]. Hubin, T. J.; McComick, J. M.; Collinson, S. R.; Buchalova, M.; Perkins, C. M.; Alcock, N. W.; Kahol, P. K.; Raghunathan, A.; Busch, D. H. J. Am. Chem. Soc. 2000, 122, 2512-2522.

[43]. Keypour, H.; Rezaeivala, M.; Valencia, L.; Salehzadeh, S.; Perez-Lourido, P.; Khavasi, H. R. Polyhedron 2009, 28, 3533-3541.

[44]. Boiocchi, M.; Bonizzoni, M.; Fabbrizzi, L.; Foti, F.; Licchelli, M.; Taglietti, A.; Zema, M. J. Chem. Soc. Dalton Trans. 2004, 2616-2620.

How to cite

Rezaeivala, M.; Daftari, S. Eur. J. Chem. 2014, 5(2), 343-350. doi:10.5155/eurjchem.5.2.343-350.959
Rezaeivala, M.; Daftari, S. Ab initio calculations of 13C NMR chemical shielding in some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety. Eur. J. Chem. 2014, 5(2), 343-350. doi:10.5155/eurjchem.5.2.343-350.959
Rezaeivala, M., & Daftari, S. (2014). Ab initio calculations of 13C NMR chemical shielding in some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety. European Journal of Chemistry, 5(2), 343-350. doi:10.5155/eurjchem.5.2.343-350.959
Rezaeivala, Majid, & Sam Daftari. "Ab initio calculations of 13C NMR chemical shielding in some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety." European Journal of Chemistry [Online], 5.2 (2014): 343-350. Web. 14 Nov. 2019
Rezaeivala, Majid, AND Daftari, Sam. "Ab initio calculations of 13C NMR chemical shielding in some N4O2, N4S2 and N6 Schiff base ligands containing piperazine moiety" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

DOI Link:


  • There are currently no refbacks.

Copyright (c)

© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.