Electronic absorption spectra and protolysis of 4- and 5-azaindan-1,3-diones
- 26 Downloads
The protolytic equilibria in a series of 2-aryl-substituted 4- and 5-azaindan-1,3-diones and the corresponding N-methylbetaines and 5,6-benzo analogs were studied by spectrophotometry. The substantial difference between the 4- and 5-aza derivatives is explained by the different effect of the anionic system on the Tr-electron density and the reactivities of the nitrogen atoms in the 4 and 5 positions. The protonation and deprotonation constants of the dipolar ions correlate linearly with the σ constants of the substituents in the 2-phenyl ring. In the case of 5,6-benzo-4-azaindan-1,3-diones, the keto group of the azaphthaloyl ring is protonated along with the dipolar ion in strongly acidic media.
KeywordsNitrogen Organic Chemistry Absorption Spectrum Nitrogen Atom Diones
Unable to display preview. Download preview PDF.
- 1.L. É. Neiland and G. Ya. Vanag, Khim. Geterotsikl. Soedin., 93 (1965).Google Scholar
- 2.I. V. Turovskii, Ya. Ya. Linaberg, and O. Ya. Neiland, Khim. Geterotsikl. Soedin., 158 (1967).Google Scholar
- 3.Ya. Ya. Linaberg and A. R. Veis, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 424 (1965).Google Scholar
- 4.O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 85 (1971).Google Scholar
- 5.Ya. Ya. Linaberg, Dissertation [in Russian], Riga (1965).Google Scholar
- 6.I. V. Turovskii, Ya. P. Stradyn', and V. P. Kadysh, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 174 (1972).Google Scholar
- 7.M. Paul and F. Long, Chem. Rev., 57, 1 (1957).Google Scholar