Abstract
The adsorption behavior of atenolol molecule over the pristine carbon nanotube and boron nitride nanotube as well as functionalized carbon nanotube was performed employing the B3LYP and CAM-B3LYP methods with 6-311G(d, p) basis set in two phases (gas and water solution). We used natural bond orbital, non-covalent interactions and the quantum theory of atoms in molecules to investigate the hydrogen bonds, interaction energies and charge transfers between the atenolol drug and nanosystems. In all cases, the process of intermolecular interaction between atenolol and nanosystems is exothermic showing that the optimized complexes are stable. The hydrogen-bonding interactions between drug and CNT–(COOH)3 play an important role for the different kinds of adsorption. In addition, data showed that there is a large charge donation and back-donation for atenolol adsorption on the surface of CNT–(COOH)3. Results indicated that although in the case of pristine carbon nanotube, the adsorption is weak, functionalization of carbon nanotube with –COOH groups can effectively modify the surface of nanotubes towards atenolol molecules adsorption and improve their solubility in water solution.
Similar content being viewed by others
REFERENCES
A. Kuster, A. C. Alder, B. I. Escher, K. Duis, K. Fenner, J. Garric, T. H. Hutchinson, D. R. Lapen, A. Pery, and J. Rombke, Integr. Environ. Assess. Manage. 6, 514 (2010).
B. Egan, J. Flack, M. Patel, and S. Lombera, J. Clin. Hypertens. 20, 1464 (2018).
N. Bertrand and J.-C. Leroux, J. Control. Release 161, 152 (2012).
C. Chen, H. Zhang, L. Hou, J. Shi, L. Wang, C. Zhang, M. Zhang, H. Zhang, X. Shi, and H. Li, J. Pharm. Pharm. Sci. 16, 40 (2013).
M. Hesabi and R. Behjatmanesh-Ardakani, Comput. Theor. Chem. 1117, 61 (2017).
H. Xu, Q. Wang, G. Fan, and X. Chu, Theor. Chem. Acc. 7, 104 (2018).
O. A. Oyetade, V. O. Nyamori, B. S. Martincigh, and S. B. Jonnalagadda, RSC Adv. 6, 2731 (2016).
K. Z. Milowska, J. Phys. Chem. C 119, 26734 (2015).
M. Mananghaya, M. A. Promentilla, K. Aviso, and R. Tan, J. Mol. Liq. 215, 780 (2016).
R. Kobayashi and R. D. Amos, Chem. Phys. Lett. 420, 106 (2006).
T. Yanai, D. P. Tew, and N. C. Handy, Chem. Phys. Lett. 393, 51 (2004).
L. Simon and J. M. Goodman, Org. Biomol. Chem. 9, 689 (2011).
M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, and G. Petersson, Gaussian 09, Revision B.01 (Gaussian, Inc., Wallingford, CT, 2009).
S. Dapprich, I. Komaromi, K. S. Byun, K. Morokuma, and M. J. Frisch, J. Mol. Struct. 461, 1 (1999).
W. L. Yim and Z. F. Liu, Chem. Phys. Lett. 398, 297 (2004).
Z. Chen, S. Nagase, A. Hirsch, R. C. Haddon, W. Thiel, and P. V. Schleyer, Angew. Chem., Int. Ed. 43, 1552 (2004).
J. Tomasi, B. Mennucci, and R. Cammi, Chem. Rev. 105, 2999 (2005).
S. Boys and F. Bernardi, Mol. Phys. 100, 65 (2002).
F. A. I. M. Biegler-Konig, AIM 2000 1.0 (Univ. Appl. Sci., Bielefeld, 2000).
W. Humphrey, A. Dalke, and K. Schulten J. Mol. Graph. 14, 33 (1996).
T. Lu and F. Chen, J. Comput. Chem. 33, 580 (2012).
E. D. Glendening, C. R. Landis, and F. Weinhold, J. Comput. Chem. 34, 1429 (2013).
Jmol-NBO Visualization Helper. http://chemgplus.blogspot.com/2013/08/jmolnbo-visualization-helper.html.
R. G. Parr, R. A. Donnelly, M. Levy, and W. E. Palke, J. Chem. Phys. 68, 3801 (1978).
R. G. Parr and W. Yang, J. Am. Chem. Soc. 106, 4049 (1984).
P. Politzer, P. Lane, J. S. Murray, and M. C. Concha, J. Mol. Model. 11, 1 (2005).
S. J. Grabowski, J. Phys. Chem. A 116, 1838 (2012).
I. Rozas, I. Alkorta, and J. Elguero, J. Am. Chem. Soc. 122, 11154 (2000).
M. Ziolkowski, S. J. Grabowski, and J. Leszczynski, J. Phys. Chem. A 110, 6514 (2006).
C. F. Matta, J. Hernandez-Trujillo, T. H. Tang, and R. F. Bader, Chem.-Eur. J. 9, 1940 (2003).
A. Shahi and E. Arunan, Phys. Chem. Chem. Phys. 16, 22935 (2014).
A. Varadwaj, P. R. Varadwaj, and B. Y. Jin, RSC Adv. 6, 19098 (2016).
E. R. Johnson, S. Keinan, P. Mori-Sanchez, J. Contreras-Garcia, A. J. Cohen, and W. Yang, J. Am. Chem. Soc. 132, 6498 (2010).
H. Xiao, J. Tahir-Kheli, and W. A. Goddard III, J. Phys. Chem. Lett. 2, 212 (2011).
ACKNOWLEDGMENTS
This work was supported by a grant from the Young Researchers club of Islamic Azad University and we thank for this valuable cooperation.
Author information
Authors and Affiliations
Contributions
Both authors participated in writing the manuscript. Both authors read and approved the final manuscript.
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interest.
Rights and permissions
About this article
Cite this article
Maryam Hesabi, Ghasem Ghasemi A CAM-B3LYP DFT Investigation of Atenolol Adsorption on the Surface of Boron Nitride and Carbon Nanotubes and Effect of Surface Carboxylic Groups. Russ. J. Phys. Chem. 94, 1678–1693 (2020). https://doi.org/10.1134/S0036024420080117
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024420080117