Conclusions
-
1.
Based on their NMR data monoazo resorcinol derivatives exist in solutions of organic solvents and in acidic aqueous media in an azo form, whereas in basic media they adopt a quinonehydrazone structure.
-
2.
The structure of bisazo resorcinol derivatives is determined by the method used to introduce the second arylazo functional group: 1,3-isomers adopt a bis(quinonehydrazone) structure, while the 1,5-isomers exhibit a bisazo structure.
-
3.
A localized tautomer of 1,3,5-trisazoresorcinol exhibits a quinonehydrazone structure for the 1,3-arylazo functional groups and an azo structure for the azo group in the 5-position. At higher temperatures the 1- and 5-arylazo functional groups undergo functional group interchange.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
H. Zollinger, Chemistry of Azo Dyes [Russian translation], Goskhimizdat, Leningrad (1960).
I. M. Korenman, Organic Reagents in Inorganic Analysis [Russian translation], Khimiya, Moscow (1980).
L. A. Fedorov, M. S. Zhukov, T. B. Petrova, and S. B. Savvin, Zh. Anal. Khim.,39, 1754 (1984).
V. Bekarek, J. Dobas, P. Vetesnik, and M. Večera, Coll. Czech. Chem. Commun.,35, 1406 (1970).
B. L. Kaul, R. Srinivasan, and K. Venkataraman, Chimia,19, 213 (1965).
T. S. Gore, P. K. Inamdar, and A. V. Patwardhan, Indian J. Chem.,8, 195 (1970).
L. A. Fedorov, Zh. Anal. Khim.,40, 29 (1985).
V. V. Negrebetskii, A. I. Bokanov, and B. I. Stepanov, Zh. Org. Khim.,16, 1708 (1980).
A. Lyčka, Coll. Czech. Chem. Commun.,47, 1112 (1982).
L. A. Fedorov, M. S. Zhukov. N. V. Korsakova, et al., Izv. Akad. Nauk SSSR. Ser. Khim., 1763 (1984).
L. A. Fedorov, M. S. Zhukov, and M. V. Ivanov, Zh. Anal. Khim.,40, 215 (1985).
L. A. Fedorov, N. I. Grebenshchikov, T. G. Akimova, and A. N. Ermakov, Izv. Akad. Nauk SSSR, Ser. Khim., 927 (1983).
A. Lyčka and P. E. Hansen, Org. Magn. Reson.,22, 569 (1984).
A. Lycka, D. Snobl, V. Machaček, and M. Vecera, ibid.,15, 390 (1981).
L. A. Fedorov, S. A. Sokolovskii, S. I. Dvoskin, and V. M. Chertov, Zh. Org. Khim.,23, 2345 (1987).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 325–332, February, 1988.
Rights and permissions
About this article
Cite this article
Fedorov, L.A., Sokolovskii, S.A., Dvoskin, S.I. et al. NMR spectra and structures in solution of resorcinol azo derivatives. Russ Chem Bull 37, 250–256 (1988). https://doi.org/10.1007/BF00957420
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00957420