European Journal of Chemistry

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

Article Sidebar

PDF
Published: Jun 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.2.343-350.959
Keywords:
DFT, GIAO, CSGT, Ab initio, Schiff base, Piperazine
Section
Research Article
Issue
Vol. 5 No. 2 (2014): June 2014
Dates
Received 2013-10-27
Accepted 2014-02-04
Published 2014-06-30


Main Article Content

Majid Rezaeivala
Department of Chemical Engineering, Hamedan University of Technology, Hamedan 65157, Iran
Sam Daftari
Department of Environmental Sciences, University of Omran and Toseeh, Hamedan, 65157, Iran

Abstract

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.


icon graph This Abstract was viewed 1713 times | icon graph Article PDF downloaded 834 times

How to Cite
(1)
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, 343-350.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

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

[2]. Ziegler, T. Chem. Rev. 1991, 91, 651-667.
http://dx.doi.org/10.1021/cr00005a001

[3]. Hohenberg, P.; Kohn, W. Phys. Rev. B. 1964, 136, 864-871.
http://dx.doi.org/10.1103/PhysRev.136.B864

[4]. Vignale, G.; Rasolt, M.; Geldard, D. J. W. Adv. Quant. Chem. 1990, 21, 235-253.
http://dx.doi.org/10.1016/S0065-3276(08)60599-7

[5]. Lee, A. M.; Handy, N. C.; Colwell, S. M. J. Chem. Phys. 1995, 103, 10095-10109.
http://dx.doi.org/10.1063/1.469912

[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.
http://dx.doi.org/10.1021/j100098a011

[8]. Zheng, G.; Hu, J.; Zhang, X.; Shen, L.; Yea, C.; Webb, G. A. J. Mol. Struct. (Theochem) 1998, 428, 283-286.
http://dx.doi.org/10.1016/S0166-1280(97)00291-1

[9]. Bagno, A.; Rastrelli, F.; Saielli, G. Chem. Eur. J. 2006, 12, 5514-5525.
http://dx.doi.org/10.1002/chem.200501583

[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.
http://dx.doi.org/10.1021/cr0683616

[13]. Vigato, P. A.; Tamburini, S.; Bertolo, L. Coord. Chem. Rev. 2007, 251, 1311-1620.
http://dx.doi.org/10.1016/j.ccr.2006.11.016

[14]. Beckmann, U.; Brooker, S. Coord. Chem. Rev. 2003, 245, 17-29.
http://dx.doi.org/10.1016/S0010-8545(03)00030-4

[15]. Radecka-Paryzek, W.; Patroniak, V.; Lisowski, J. Coord. Chem. Rev. 2005, 249, 2156-2175.
http://dx.doi.org/10.1016/j.ccr.2005.02.021

[16]. Bouwman, E.; Reedijk, J. Coord. Chem. Rev. 2005, 249, 1555-1581.
http://dx.doi.org/10.1016/j.ccr.2004.10.010

[17]. Vigato, P. A.; Tamburini, S. Coord. Chem. Rev. 2008, 252, 1871-2154.
http://dx.doi.org/10.1016/j.ccr.2007.10.030

[18]. Okawa, H.; Furutachi, H.; Fenton, D. E. Coord. Chem. Rev. 1998, 174, 51-75.
http://dx.doi.org/10.1016/S0010-8545(97)00082-9

[19]. Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410-421.
http://dx.doi.org/10.1039/b307853c

[20]. Grigoropoulou, G.; Clark, J. H.; Elings, J. A. Green Chem. 2003, 5, 1-7.
http://dx.doi.org/10.1039/b208925b

[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.
http://dx.doi.org/10.1080/00268977400100711

[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.
http://dx.doi.org/10.1021/ja00179a005

[26]. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1-8.
http://dx.doi.org/10.1016/0009-2614(92)85733-Q

[27]. Keith, T. A, Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223-231.
http://dx.doi.org/10.1016/0009-2614(93)89127-4

[28]. Prakash, R. V.; Rasul, G.; Surya, P. G. K.; Olah, G. A. J. Org. Chem. 2003, 68, 3507-3510.
http://dx.doi.org/10.1021/jo030110z

[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.
http://dx.doi.org/10.1016/j.molstruc.2005.10.041

[30]. Meng, Z.; Carper, W. R. J. Mol. Struct. (Theochem.) 2002, 588, 45-53.
http://dx.doi.org/10.1016/S0166-1280(02)00116-1

[31]. Gallant, A. J.; Hui, J. K. H.; Zahariev, F. E.; Wang, Y. A.; MacLachlan, M. J. J. Org. Chem. 2005, 70, 7936-7946.
http://dx.doi.org/10.1021/jo050742g

[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.
http://dx.doi.org/10.1016/j.saa.2009.09.053

[34]. Sheikhshoaie, I.; Saheb, V. Spectrochim. Acta A 2010, 77, 1069-1076.
http://dx.doi.org/10.1016/j.saa.2010.08.075

[35]. Infante-Castillo, R. J. Mol. Struct. (Theochem) 2010, 940, 124-128.
http://dx.doi.org/10.1016/j.theochem.2009.10.026

[36]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
http://dx.doi.org/10.1063/1.464913

[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.
http://dx.doi.org/10.1063/1.471789

[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.
http://dx.doi.org/10.3998/ark.5550190.0010.a26

[41]. Larkins, H. L.; Hamilton, A. D. Tetrahedron Lett. 1986, 27, 2721-2724.
http://dx.doi.org/10.1016/S0040-4039(00)84626-2

[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.
http://dx.doi.org/10.1021/ja990366f

[43]. Keypour, H.; Rezaeivala, M.; Valencia, L.; Salehzadeh, S.; Perez-Lourido, P.; Khavasi, H. R. Polyhedron 2009, 28, 3533-3541.
http://dx.doi.org/10.1016/j.poly.2009.05.083

[44]. Boiocchi, M.; Bonizzoni, M.; Fabbrizzi, L.; Foti, F.; Licchelli, M.; Taglietti, A.; Zema, M. J. Chem. Soc. Dalton Trans. 2004, 2616-2620.
http://dx.doi.org/10.1039/b408085h

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).