Abstract
Optimized molecular structures and total energies of 3-fluoro-, 3-chloro-, 3-bromopyridine (3‑FP, 3-CP, and 3-BP) molecules in vacuum, benzene, toluene, chloroform, dichloromethane, ethanol, dimethylsulfoxide and water media were investigated using DFT/B3LYP-6311++G(d,p) method. Moreover, in order to be able to see the effects of changing physical conditions, the thermochemical properties of the structures have been calculated in different temperatures and solvent media. Vibrational frequencies of 3-FP, 3-CP, and 3-BP molecules in vacuum and solvent media were calculated and compared to experimental data from the literature. Also, the chemical reactivities of the structures were calculated from HOMO–LUMO energies. Molecular electrostatic potential maps were plotted and atomic charges of each atom were determined. As a result of the study, it was determined that the molecular parameters of these three structures were slightly influenced by the changing solvent polarity, but the vibration frequencies and other chemical properties have very seriously affected.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
W. R. Dolbier and Y. L. Xu, J. Fluorine Chem. 123, 71 (2003).
Y. Nibu, R. Marui, and H. Shimada, Chem. Phys. 442, 7 (2007).
S. Wöhlert, I. Jess, and C. Nather, Inorg. Chem. Acta 407, 243 (2013).
H. S. Green, W. Kynaston, and H. M. Paisly, Spectrochim. Acta 19, 549 (1963).
W. S. Saari, W. Halczenko, S. W. King, J. R. Huff, J. P. Guare, C. A. Hunt, W. C. Randall, P. S. Anderson, V. J. Lotti, D. A. Taylor, and B. V. Clinechmidt, J. Med. Chem. 26, 1696 (1983).
T. Miyamoto, H. Egawa, and J. Matsumoto, Chem. Pharm. Bull. 35, 2280 (1987).
P. Boopalachandran and J. Laane, Spectrochim. Acta. A. 79, 1191 (2011).
E. Akalin and S. Akyüz, J. Mol. Struct. 993, 390 (2011).
P. Boopalachandran, H. L. Sheu, and J. Laane, J. Mol. Struct. 1023, 61 (2012).
M. Orozco and F. J. Luque, Chem. Rev. 100, 4187 (2000).
M. A. Halim, D. M. Shaw, and R. A. Poirier, J. Mol. Struct.: THEOCHEM 960, 63 (2010).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, et al., Gaussian 03, Revision D.01 (Gaussian Inc., Wallingford, CT, 2004).
R. D. Dennington, T. A. Keith, and J. M. Millam, GaussView 5 (Gaussian Inc., 2008).
N. Sundaraganesan, G. Elango, S. Sebastian, and P. Subramani, Indian J. Pure Appl. Phys. 47, 481 (2009).
M. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4 (Warsaw, 2004).
R. G. Parr, J. Am. Chem. Soc. 121, 1922 (1999).
V. Vasylyeva, O. V. Shishkin, A. V. Maleev, and K. Merz, Cryst. Growth Des. 12, 1032 (2012).
F. M. A. Noa, S. A. Bourne, H. Su, E. Weber, and L. R. Nassimbeni, Cryst. Growth Des. 16, 4765 (2016).
L. Qiu, X. H. Ju, and H. M. Xiao, J. Chin. Chem. Soc.-Taip. 52, 405 (2005).
J. W. Ochterski, Thermochemistry in Gaussian (Gaussian Inc., 2000).
http://webbook.nist.gov/cgi/inchi?ID=C372474& Mask=80.
R. Shahidha, A. A. Al-Saadi, and S. Muthu, Spectrochim. Acta, A 134, 127 (2015).
ACKNOWLEDGMENTS
This study was funded by the Çankırı Karatekin University Scientific Research Fund (project no. EFF20217B33).
Author information
Authors and Affiliations
Corresponding author
Additional information
1The article is published in the original.
Rights and permissions
About this article
Cite this article
Mustafa Tuğfan Bilkan Density Functional Theory Study of Solvent Effects on 3-Fluoro-, 3-Chloro-, 3-Bromopyridine. Russ. J. Phys. Chem. 92, 1920–1931 (2018). https://doi.org/10.1134/S0036024418100059
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024418100059