Abstract
The13C NMR, UV and IR absorption spectra of 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-pyridinedicarboxylic acids were recorded and their spectral parameters were assigned. The influence of electronic properties of the substituents on the direction of the chemical shifts is discussed. The influence of substituents in the molecule on λmax and εmax of the UV-spectral band is disscused. Analizing13C NMR, UV, and IR absorption spectra it was found that there is a disturbance of mutual electronic interaction of substituents by a steric ortho effect. This effect is reflected in paramagnetism of the carboxyl group, the value of the correlation coefficient, deformation C−O stretching bands, and the decrease in the intensity of the CT band.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
L. Chmurzynski and Z. Pawlak, J. Mol. Struct.,80, 235 (1982).
L. Chmurzynski, A. Liwo, and A. Wawrzynow, J. Mol. Struct.143, 375 (1986).
M. Cigniti and F. Gata, Spectrochim. Acta.,41A/11, 1287 (1985).
L. Chmurzynski and A. Liwo, J. Mol. Struct.,218, 129 (1990).
A. Puszko, J. Crystal and Spectr. Res.,23, 23 (1993).
S. A. Hata, Bull. Chem. Soc. Jpn.,31, 255 (1958).
J. Roček and T.-Y. Peng, J. Am. Chem. Soc.,99, 7622 (1977).
G. E. Dunn, G. K. J. Lee, and H. Thimm, Can. J. Chem.,50, 3017 (1972).
S. Lis, Z. Hnatejko, and M. Elbanowski, Bull. Pol. Acad. Sci. Chem.,42/1, 49 (1994).
G. R. Germaine and W. G. Murrel, Photochem. Photobiol.,17, 145 (1973).
t. Sugiyama, M. Kanai, and S. Takenaka, Bull. Chem. Soc. Jpn.,58, 1331 (1985).
O. Efimovsky and P. Rumpf, Bull. Soc. Chim. Fr., 648 (1954).
A. F. Lindenstruth and C. A. Vander Werf, J. Am. Chem. Soc.,71, 3020 (1949).
R. Jokela, Magn. Res. Chem.,30, 681 (1992).
F. W. Wehrli and T. Wirthlin, Interpretacja widm w spektroskopii13C NMR. PWN, Warszawa, (1985), p. 318.
Additional information
Department of Organic Chemistry, University of Economics, PL-53 342 Wroclaw, Poland, Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 210–218, February, 1999.
Rights and permissions
About this article
Cite this article
Wasylina, L., Kucharska, E., Weglinski, Z. et al. The13C NMR, UV and IR absorption spectra of pyridinedicarboxylic acids. Chem Heterocycl Compd 35, 186–194 (1999). https://doi.org/10.1007/BF02251707
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02251707