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Quantum Chemical Computational Study on Chlorocholine Chloride and Bromocholine Bromide
Corresponding Author(s) : M. Karakaya
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
This study deals with the conformational and spectral analysis of chlorocholine chloride and bromocholine bromide by means of theoretical calculations. The optimized molecular structures and vibrational frequencies and also 1H and 13C NMR shift values of the compounds have been calculated using density functional theory method with 6-311++G(d,p) basis set. The comparison of their experimental and calculated IR, Raman and NMR spectra of the compounds has indicated that the spectra of two optimized conformers can simultaneously exist in one experimental spectrum. Thus, it was concluded that the compounds simultaneously exist in two conformations in the ground state. The natural bond orbital (NBO) analysis has also supported the simultaneous exiting of two conformers for the both compounds. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program.
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References
M.D. Segall, M.C. Payne and R.N. Boyes, Mol. Phys., 93, 365 (1998).
A.S. Davies, W.O. George and S.T. Howard, Phys. Chem. Chem. Phys., 5, 4533 (2003).
J. Song, M.S. Gordon, C.A. Deakyne and W. Zheng, J. Phys. Chem., A108, 11419 (2004).
T. Marino, N. Russo, E. Tocci and M. Toscano, Theor. Chem. Acc., 107, 8 (2001).
J. Caillet, P. Claverie and B. Pullman, Acta Cryst., B34, 3266 (1978).
J.K. Herdklotz and R.L. Sass, Biochem. Biophys. Res. Commun., 40, 583 (1970).
K. Frydenvang and B. Jensen, Acta Cryst., B52, 184 (1996).
T. Svinning and H. Sorum, Acta Cryst., B31, 1581 (1975).
S. Jagner and B. Jensen, Acta Cryst., B33, 2757 (1977).
B. Pullman and P. Courriere, Mol. Pharmacol., 8, 612 (1972).
M.J. Frisch, G.W. Trucks, H.B. Schlegal, G.E. Scuseria, M.A. Robb, J.R. Cheesman, V.G. Zakrzewski, J.A. Mortgomerg Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, J. Mennucci, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malich, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stetanov, G. Liu, A. Liashenko, P. Piskorz, J. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A.Al. Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chenp, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Pittsburgh PA (2003).
A. Frisch, A.B. Nielsen and A.J. Holder, Gauss View User Manual, Gaussian Inc., Pittsburg PA (2001).
Computional Chemistry: A Pratical Guide for Applying Techniques to Real-World Problems (Electronics), D.C. Young, John Wiley & Sons, Inc, New York (2001).
M.H. Jamroz, Vibrational Energy Distribution Analysis, VEDA 4, Warsaw (2004).
R.F.W. Bader, Atoms in Molecules, A Quantum Theory, Oxford University Press, Oxford, UK (1990).
J.R. Cheeseman, G.W. Trucks, T.A. Keith and M.J. Frisch, J. Chem. Phys., 104, 5497 (1996).
T.A. Keith and R.F.W. Bader, Chem. Phys. Lett., 210, 223 (1993).
R. Ditchfield, Mol. Phys., 27, 789 (1974).
C.M. Rohlfing, L.C. Allen and R. Ditchfield, Chem. Phys., 87, 9 (1984).
http://www.sigmaaldrich.com/european-export.html, Sigma-Aldrich Electronic Web Page, Sigma-Aldrich Coop., New York (2006).
J. Hjortas and H. Sorum, Acta Cryst., B27, 1320 (1971).
M.E. Senko and D.H. Templeton, Acta Cryst., 13, 281 (1960).
http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng Spectral Database for Organic Compounds Web Page, National Institute of Advanced Industrial Science and Technology, Japan (2001).
A.E. Reed, L.A. Curtis and F. Weinhold, Chem. Rev., 88, 899 (1988).
J.P. Foster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980).
A.E. Reed and F. Weinhold, J. Chem. Phys., 83, 1736 (1985).
A.D. Becke, J. Chem. Phys. Rev., 98, 5648 (1993).
Frontier Orbitals and Organic Chemical Reactions, I. Fleming, Wiley, London (1976).
K. Fukui, Science, 218, 747 (1982).
S.I. Gorelsky, SWizard Program, Revision 4.5., http://www.sg.chem.net/,University of Ottawa, Ottawa, Canada (2010).