Abstract
The1H and13C NMR spectra of 2, 5-disubstituted 1,3,4-oxadiazoles with aliphatic, aromatic, and hetero-aromatic substituents have been described and interpreted. The electronic effect of the 1,3,4-oxadiazole group as a benzene ring substituent was evaluated using13C NMR spectroscopy.
Similar content being viewed by others
References
R. Milcent and G. Barbier, J. Heterocycl. Chem.,20, 77 (1983).
G. Aranda, M. Dessolin, M. Golfier, and M.-G. Guillerez, Org. Magn. Reson.,18, 159 (1982).
Y. Terui, M. Yamakawa, T. Honma, Y. Tada, and K. Tori, Heterocycles,19, 222 (1982).
R. W. Saalfrank, B. Weiss, K. Peters, and H. G. von Schnering, Chem. Ber., 118, 4028 (1985).
V. M. Feygelman, J. K. Walker, A. R. Katritzky, and Z. Dega-Szafran, Chem. Scripta,29, 241 (1989).
J. K. Walker, A. R. Katritzky, and Z. Dega-Szafran, Chem. Scripta,29, 241 (1989).
M. M. Girges, M. A. Hanna, M. Berghot, and D. Rasala, Chem. Papers,46, 272 (1992).
H. Tashtoush, M. Al-Talib, and N. Oden, Ann., No. 3, 291 (1992).
I. S. Poddubnyi, L. I. Belen'kii, and M. M. Krayushkin, Khim. Geterotsikl. Soedin., No. 5, 686 (1994).
J. Beeby, S. Sternhell, and T. Hoffman-Ostenhof, Anal. Chem.,45, 1571 (1973).
B. I. Ionin, B. A. Ershov, and A. N. Kol'tsov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningradsk. Otdel., Leningrad (1983), pp. 167, 170, 171.
N. I. Popik, M. V. Shablygin, L. V. Vilkov, A. S. Semenova, and T. V. Kravchenko, Vysokornolek. Soedin.,25B, 38 (1983).
D. F. Ewing, Org. Magn. Reson.,12, 499 (1979).
G. L. Nelson, G. C. Levy, and J. D. Cargioli, J. Am. Chem. Soc.,94, 3088 (1972).
C. G. Swain and E. C. Lupton, J. Am. Chem. Soc.,90, 4328 (1968).
G. C. Levy and G. L. Nelson, Handbook on Carbon-13 Nuclear Magnetic Resonance for Organic Chemists [Russian translation], Mir, Moscow (1975), p. 118.
D. Del Mazza, M. G. Reinecke, and W. B. Smith, Magn. Reson. Chem.,27, 187 (1989).
O. P. Shkurko, S. G. Baram, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 1, 66 (1983).
G. W. Sovocool and N. K. Wilson, J. Org. Chem.,47, 4032 (1982).
S. G. Baram, O. P. Shkurko, and V. P. Mamaev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 294 (1983).
E. M. Schulman, K. A. Christensen, D. M. Grant, and C. Walling, J. Org. Chem.,39, 2686 (1974).
S. Lotjonen and P. Ayras, Finn. Chem. Lett., No. 8, 260 (1978).
L. I. Belen'kii, V. S. Bodganov, L. A. Abronin, G. P. Gromovo, M. A. Cheskis, and R. Z. Zakharyan, Chem. Scripta.,25, 266 (1985).
O. Bashansen and S. Samdai, J. Mol. Struct.,128, 115 (1985); Ref. Zh. Khim., 20B1087 (1985).
Additional information
N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 834–842, June, 1994. Original article submitted April 8, 1994.
Rights and permissions
About this article
Cite this article
Poddubnyi, I.S., Belen'kii, L.I., Struchkova, M.I. et al. 1H and13C NMR spectra of 1,5-disubstituted 1,3,4-oxadiazoles. Chem Heterocycl Compd 30, 729–737 (1994). https://doi.org/10.1007/BF01166317
Issue Date:
DOI: https://doi.org/10.1007/BF01166317