Abstract
In this paper, the stabilities and hydrogen bond interactions of 4-chloro-1-naphthol, 1-hydrox-ynaphthalene and 1,4-dihydroxynaphthalene dimers have been theoretically investigated by means of study on binding energies with nonlocal hybrid three-parameter Lee-Yang-Parr, B3LYP, and M06-class functional calculations. Calculations on dimers aim to provide as a test of the efficacy of M06 calculations for intermolecular interaction calculations and more strongly bound systems. For hydroxyl- and halo-substituted derivatives of naphthalene, total electronic energies, their correction for the zero point vibrational energies with some calculated thermodynamic properties and their relative differences are together in order to discuss the rotamer structures. Static (hyper) polarizabilities and the electric dipole moments, frontier molecular orbital energy gaps and the relationships between them have been interpreted. Generally, they are seen that the calculated geometric parameters and spectral results were in a good agreement with the corresponding experimental data.
Similar content being viewed by others
References
J. E. Amoore and E. Hautala, J. Appl. Toxicol. 3, 272 (1983).
J. P. Daw Son, W. W. Thayer and J. F. Desfoges, Blood 13, 1113 (1987).
S. J. Fanbergh, Arch. Derm. Syph. 43, 53 (1940).
M. Talukder and C. R. Kates, Kirk-Othmer Encyclopedia of Chemical Technology (Wiley, 1999–2014).
V. V. Mezheritskii, M. S. Korobov, O. M. Golyanskaya, N. I. Omelichkin, L. G. Minyaeva, G. S. Borodkin, A. A. Milov, A. V. Tsukanov, and A. D. Dubonosov, Russ. J. Org. Chem. 48, 241 (2012).
M. I. Rodriguez-Caceres, R. A. Agbaria, and I. M. Warner, J. Fluoresc. 15, 185 (2005).
P. D. Ahn, R. Bishop, D. C. Craig, and M. L. Scudder, J. Inclus. Phenom. Mol. Rec. Chem. 20, 267 (1994).
P. D. Ahn, R. Bishop, D. C. Craig, and M. L. Scudder, J. Inclus. Phenom. Mol. Rec. Chem. 23, 313 (1995).
Y. B. Rokade and R. Z. Sayyed, Rasayan J. Chem. 2, 972 (2009).
A. Behal and B. Bahal, A Textbook of Organic Chemistry (S. Chand and Company, New Delhi, 2005).
B. P. Patel, E. J. Pressman, and R. Mills, Int. Patent WO/2005/040080 (2005).
S. Grimme, J. Comput. Chem. 27, 1787 (2006).
J. Sponer, J. Leszczynski, and P. Hobza, J. Phys. Chem. 100, 1965 (1996).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 78 (1988).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision C.02 (Gaussian, Inc., Pittsburgh, PA, 2003).
D. C. Young, Computional Chemistry: A Pratical Guide for Applying Techniques to Real-World Problems (Wiley, New York, 2001).
M. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4 (Warsaw, 2004).
A. Frisch, A. B. Nielsen, and A. J. Holder, Gauss View User Manual (Gaussian Inc., Pittsburgh, 2001).
R. Ditchfield, Mol. Phys. 27, 789 (1974).
C. M. Rohlfing, L. C. Allen, and R. Ditchfield, Chem. Phys. 87, 9 (1984).
S. Miertus, E. Scrocco, and J. Tomasi, J. Chem. Phys. 55, 1171 (1981).
Y. Zhao and D. G. Truhlar, Theor. Chem. Acc. 120, 215 (2008).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 09, Revision D.01 (Gaussian Inc., Wallingford CT, 2013).
S. F. Boys and F. Bernardi, Mol. Phys. 19, 553 (1970).
R. Zhang, B. Du, G. Sun, and Y. Sun, Spectrochim. Acta, Part A 75, 1115 (2010).
A. K. Jissy, U. P. M. Ashik, and A. Datta, J. Phys. Chem. C 115, 12530 (2011).
E. Benassi and F. Spagnolo, J. Solution Chem. 39, 11 (2010).
P. S. Liyanage, R. M. de Silva, and K. M. N. de Silva, J. Mol. Struct.: THEOCHEM 639, 195 (2003).
M. C. R. Delgado, V. Hernandez, J. Casado, J. T. Lopez Navarre, J. M. Raimundo, P. Blanchard, and J. Roncali, J. Mol. Struct. 651, 151 (2003).
J. P. Abraham, D. Sajan, V. Shettigar, S. M. Dharmaprakash, I. Nemec, I. H. Joe, and V. S. Jayakumar, J. Mol. Struct. 917, 27 (2009).
M. Karabacak, M. Cinar, M. Kurt, A. Poiyamozhi, and N. Sundaraganesane, Spectrochim. Acta, Part A 117, 234 (2014).
E. R. Sokolowska and B. Marciniak, Acta Crystallogr. C 65, 207 (2009).
Sigma-Aldrich Electronic Web Page (Sigma Co., Aldrich, New York, 2006), http://www.sigmaaldrich.com/spectra/ftir/FTIR007548.PDF (Accessed March 2013); http://www.sigmaaldrich.com/spectra/rair/RAIR012403.PDF (Accessed March 2013).
B. Lu, L. Zeng, J. Xu, Z. Le, and H. Rao, Eur. Polym. J. 45, 2279 (2009).
Spectral Database for Organic Compounds (National Institute of Advanced Industrial Science and Technology, Japan, 2011). http://sdbs.db.aist.go.jp (Accessed March 2013).
F. L. Gervasio, R. Chelli, P. Procacci, and V. Schettino, Proteins 48, 117 (2002).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Karakaya, M., Çiçek, A., Ucun, F. et al. Investigations on stabilities and intermolecular interactions of different naphthalene derivatives dimers by using B3LYP and M06-2X density functional calculations. Russ. J. Phys. Chem. 88, 2137–2145 (2014). https://doi.org/10.1134/S0036024414120127
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024414120127