80
M. Szafran et al. / Journal of Molecular Structure 797 (2006) 66–81
[14] C. Møller, M.S. Plesset, Phys. Rev. 46 (1934) 618.
[15] G.W. Trucks, E.A. Salter, C. Sosa, R.J. Bartlett, Chem. Phys. Lett.
147 (1988) 359.
[16] T.J. Dunning Jr., J. Chem. Phys. 90 (1989) 1007.
[17] W.J. Hehre, L. Random, P.v.R. Schleyer, J.A. Pople, Ab Initio
Molecular Orbital Theory, Wiley, New York, 1989.
[18] IUPAC Commission on Molecular Structure on Spectroscopy, Pure
Appl. Chem. 50 (1978) 1707.
[19] P. Pulay, G. Fogarasi, F. Pang, J.E. Boggs, J. Am. Chem. Soc. 101
(1979) 2550.
[20] G. Keresztury, G. Jalsovszky, J. Mol. Struct. 10 (1971) 304.
[21] K. KuBulat, PhD dissertation, University of Florida, Gainesville, Fl,
USA, 1989.
respectively, and the plots are linear with r = 0.999 and
0.997. The correlation between the computed infrared
absorption intensities (A) and the experimental (Irel) is less
satisfactory, but the corresponding plot is linear with
r = 0.925. The results lend plausibility to the applied way
of assigning the vibrational spectrum of the title molecule
in the solid state.
Carboxy-1-methylpyridinium chlorides are character-
1
ized by H and 13C chemical shifts. The linear correlations
between the experimental and calculated magnetic isotro-
pic shielding tensors (by GIAO) are better for carbon
atoms than for protons.
[22] W.B. Person, K. KuBulat, personal communication, 1989.
[23] D. Hadzˇi (Ed.), Theoretical Treatment of Hydrogen Bonding, Wiley,
Chichester, 1977.
Acknowledgements
[24] The Aldrich Library of FTIR spectra, second ed., Sigma–Aldrich Co.,
USA, 1997, p. 3785B.
[25] M. Szafran, J. Koput, J. Baran, T. Głowiak, J. Mol. Struct. 123
(1997) 436–437.
[26] M. Szafran, J. Koput, Z. Dega-Szafran, J.S. Kwiatkowski, Vibra-
tional Spectr. 23 (2000) 1.
The authors are grateful to Professor W.B. Person for
providing the PACK program and stimulating discussion.
´
Calculations were performed at the Poznan Supercomput-
ing and Networking Centre. The financial support for this
work was provided by Adam Mickiewicz University and
Poznan University of Economy, Grant No. 51103-503.
[27] S. Bratos, H. Ratajczak, P. Viot, in: J.C. Dore, J. Teixeire (Eds.),
Hydrogen Bonded Liquids, Kluver Academic Publishers, Dordrecht,
1991, p. 221, and references cited therein.
[28] H. Ratajczak, W.J. Orville-Thomas (Eds.), Molecular Interactions,
vol. I, Wiley, New York, 1980.
References
[29] S. Bratos, D. Hadzi, J. Chem. Phys. 27 (1957) 991.
[30] M.E. Jacox, J. Phys. Chem. Ref. Data 3 (1994).
[31] W.B. Person, K. Szczepaniak, M.M. Szczesniak, J.G. Del Bene, in:
R. Fausto (Ed.), Recent Experimental and Computational Advanc-
es in Molecular Spectroscopy, NATO ASI Series, Kluwert,
Dordrecht, 1993, pp. 141–169.
[32] A.T. Dubis, S.J. Grabowski, D.B. Romanowska, T. Misiaczek,
J. Leszczynski, J. Phys. Chem. A. 106 (2002) 10613.
[33] P. Tarakeshwar, S. Manogaran, J. Mol. Struct. (Theochem) 417
(1997) 255.
[34] P. Pulay, X. Zhou, G. Fogarasi, in: R. Fausto (Ed.), Recent
Experimental and Computational Advances in Molecular Spectros-
copy, Kluver Academic, Netherlands, 1993, pp. 88–111.
[35] M. Alcolea Palafox, Recent Res. Dev. Phys. Chem. 2 (1998) 213–232.
[36] A.P. Scott, L. Radom, J. Phys. Chem. 100 (1996) 16502.
[37] M. Alcolea Palafox, V.K. Rastogi, Spectrochim. Acta A 58 (2002) 411.
[38] K. Szczepaniak, M.M. Szczesniak, W.B. Person, J. Phys. Chem. A
104 (2000) 3852.
[1] Beilstein 22 (1), E III/IV, 330, 462.
[2] M. Florkin, E.H. Stotz (Eds.), Comprehensive Biochemistry, Elsevier,
Amsterdam, 1965, p. 224.
[3] J.R. Cannon, J.S. Edmonds, K.A. Francesconi, C.L. Raston, J.B.
Saunders, B.W. Skelton, A.H. White, Aust. J. Chem. 34 (1981) 787.
[4] M. Szafran, J. Koput, Z. Dega-Szafran, M. Pankowski, J. Mol.
Struct. 614 (2002) 97.
[5] M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, M. Pankowski,
K. Stobiecka, Chem. Phys. 289 (2003) 201.
[6] M. Szafran, J. Koput, Z. Dega-Szafran, A. Katrusiak, J. Mol. Struct.
700 (2004) 109.
[7] E.M. Kosover, J.W.J. Patron, Org. Chem. 26 (1961) 1318.
[8] E.E. Smissman, G. Hite, J. Am. Chem. Soc. 81 (1959) 1201.
[9] G.M. Sheldrick, SHELXS-97, Program for Solution Crystal Struc-
ture, University of Go¨ttingen, Go¨ttingen, Germany, 1997.
[10] G.M. Sheldrick, SHELXL-97, Program for Solution Crystal Struc-
ture Refinement, University of Go¨ttingen, Go¨ttingen, Germany,
1997.
[39] K. Szczepaniak, W.B. Person, D. Hadzˇi, J. Phys. Chem. A 109 (2005)
6710.
[40] M. Alcolea Palafox, M. Gill, N.J. Nunez, V.K. Rastogi, L. Mittal, R.
Sharma, Int. J. Quantum Chem. 103 (2005) 394.
[41] Y.I. Binev, M.K. Georgieva, L.I. Daskalowa, Spectrochim. Acta A 60
(2004) 2601.
[42] A. Novak, Struct. Bond. 18 (1974) 257.
[43] A. Les, L. Adamowicz, M.J. Nowak, L. Lapinski, Spectrochim. Acta
48A (1992) 1385.
[11] 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, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone,
B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson,
H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda,
J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,
H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross,
C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev,
A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala,
K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg,
V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O.
Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Fores-
man, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski,
B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi,
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.
Chen, M.W. Wong, C. Gonzalez, J.A. Pople, GAUSSIAN 03,
Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
´
[44] D. Michalska, W. Zierkiewicz, D.C. Bienko, W. Wojciechowski,
T. Zeegers-Huyskens, J. Phys. Chem. A 105 (2001) 8734.
[45] A.J. Boulton, A. McKillop, in: A.R. Katritzky, C.W. Rees (Eds.),
Comprehensive Heterocyclic Chemistry, vol. 2, Part 2A, Pergamon
Press, Oxford, 1984, p. 1.
[46] R. Dichfield, Mol. Phys. 27 (1974) 789.
[47] D.A. Forsyth, A.B. Sebag, J. Am. Chem. Soc. 119 (1997) 9483.
´
[48] B. Osmiałowski, E. Kolehmainen, R. Gawinecki, Magn. Reson.
Chem. 39 (2001) 334.
[49] C.J. Pouchert, J. Behnke (Eds.), The Aldrich Library of 13C and 1H
FT-NMR Spectra, first ed., vol. 3, 1993.
[50] E. Pretsch, P. Buhlmann, C. Affolter, Structure Determination of
Organic Compounds, Tables of Spectral Data, third ed., Springer,
Berlin, 2000.
[12] A.D. Becke, J. Chem. Phys. 98 (1994) 5648.
[13] P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys.
Chem. 98 (1994) 11623.