Abstract
Salts of N-nitro-O-(4-nitrophenyl)hydroxylamine were synthesized by a new method of oxidative nitration, involving the reaction of O-(4-nitrophenyl)hydroxylamine with KNO2 or NaNO2 in the presence of PhI(OAc)2 or PhIO as oxidants. When using Na15NO2, the samples containing the nitro group labeled with the 15N isotope were obtained. Acidification of the appropriate salt gave N-nitro-O-(4-nitrophenyl)hydroxylamine. It is the first N-nitrohydroxylamine isolated in the H-form. Its thermal stability was investigated and the probable mechanism of decomposition was suggested. From a comparison of the 14N and 15N NMR spectra of N-nitro-O-(4-nitrophenyl)hydroxylamine with those of its O- and N-methylated derivatives, its equilibrium with the aci-form (N=NOOH) was inferred.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. N. Khodot, I. E. Chlenov, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 1994, 178 [Russ. Chem. Bull., Int. Ed., 1994, 43, 174].
E. N. Khodot, I. M. Petrova, O. V. Anikin, I. E. Chlenov, Izv. Akad. Nauk, Ser. Khim., 1995, 2276 [Russ. Chem. Bull., Int. Ed., 1995, 44, 2183].
M. S. Klenov, A. M. Churakov, O. V. Anikin, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2008, 625 [Russ. Chem. Bull., Int. Ed., 2008, 57, 638].
O. A. Anikin, G. V. Pokhvisneva, D. L. Lipilin, A. V. Mezhenin, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2009, 1981 [Russ. Chem. Bull., Int. Ed., 2009, 58, 2043].
V. N. Yandovich, B. V. Gidaspov, I. V. Tselinskii, Usp. Khim., 1980, 49, 461 [Russ. Chem. Rev. (Engl. Transl.), 1980, 49, 237].
E. N. Khodot, O. V. Anikin, I. E. Chlenov, Izv. Akad. Nauk, Ser. Khim., 1996, 1740 [Russ. Chem. Bull., Int. Ed., 1996, 45, 1649].
S. L. Ioffe, A. L. Blyumenfeld, A. S. Shashkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 246 [Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.), 1978, 27, 218].
A. M. Churakov, S. E. Semenov, S. L. Ioffe, Y. A. Strelenko, V. A. Tartakovsky, Mendeleev Commun., 1995, 102.
Yu. A. Strelenko, N. M. Sergeyev, J. Mol. Struct., 1996, 378, 61.
P. K. Bhattacharyya, B. P. Dailey, J. Chem. Phys., 1973, 59, 5852.
A. H. Clemens, J. H. Ridd, J. P. B. Sandall, J. Chem. Soc. Perkin Trans. 2, 1984, 1667.
M. Ali, J. H. Ridd, J. Chem. Soc. Perkin Trans. 2, 1986, 327.
V. A. Shlyapochnikov, Kolebatel’nye spektry alifaticheskih nitrosoedinenii [Vibrational Spectra of Aliphatic Nitro Compounds], 2nd Ed., Yoshkar Ola, Mari State University, 2007, p. 157 (in Russian).
A. J. Castellino, H. Rapoport, J. Org. Chem., 1984, 49, 1348.
F. Arndt, in Organic Syntheses, 15, Wiley, New York, 1935, p. 3.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1985–1994, October, 2009.
Rights and permissions
About this article
Cite this article
Klenov, M.S., Churakov, A.M., Anikin, O.V. et al. Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine. Russ Chem Bull 58, 2047–2057 (2009). https://doi.org/10.1007/s11172-009-0281-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-009-0281-2