An intramolecular charge-transfer complex in hydrogenated quinolines
The IR spectra of 6R-2,2,4-trimethyl-1,2-dihydroquinolines (I) and 6-R2,2,4-ttimethyl-1,2,3,4-tetrahydroquinolines (II) with R=H, CH3, OCH3, and OC2H5 and those of their acetyl derivatives have been studied. The change in the intensity and the frequencies of the bands of the stretching vibrations of the C–N and C=C bonds and the ring with a change in the structure of the molecule have been considered. The considerable differences in the IR and UV spectra of I and II are explained by the fact that in the I series the interaction between the pelectrons of the nitrogen and the π-electrons of the double bond (of the CTC type) and in the II series that of the ϱ-electrons of the nitrogen with the aromatic ring is predominant.
KeywordsNitrogen Organic Chemistry Double Bond Acetyl Aromatic Ring
Unable to display preview. Download preview PDF.
- 1.L. P. Zalukaev, R. P. Vorob'eva, and E. N. Ivanova, ZhPS [Journal of Applied Spectroscopy],6, 366, 547, 1967.Google Scholar
- 2.L. P. Zalukaev, R. P. Vorob'eva, and G. A. Vanina, KhGS, collection:1, p. 124, 1967.Google Scholar
- 3.A. R. Katritzky, ed., Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow and Leningrad, 1966.Google Scholar
- 4.Yu. N. Sheinker and E. M. Peresleni, ZhFKh,36, 1705, 1962.Google Scholar
- 5.K. Nakanishi, Absorption Spectroscopy. Practical [Russian translation], Mir, Moscow, 1965.Google Scholar
- 6.L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL, Moscow, p. 107, 1963.Google Scholar
- 7.L. Ferguson and J. Nnadi, J. Chem. Educ.,42, 529, 1959.Google Scholar
- 8.A. R. Katritzky and R. A. Jones, J. Chem. Soc., 2067, 1959.Google Scholar
- 9.D. A. Ramsay, J. Am. Chem. Soc.,74, 72, 1952.Google Scholar