Conclusions
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1.
The absorption bands In the UV spectra of 1-methylhydrazides of aromatic acids have been assigned to specific types of electronic transitions. It has been shown that the amide fragment plays the decisive role in determining the nature of the electronic transitions of these molecules.
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2.
It has been shown that strong intermolecular hydrogen bonds NH... N are present in these compounds. The center of basicity in the 1-aroyl-1-methylhydrazines when they interact with phenol is the oxygen atom of the C=O group. The independence of its electron-donor strength from any influence of the para substituent on the aromatic ring and from the frequency νC=O in the IR spectra indicates a partial breakdown of conjugation of the benzene ring and the carbonyl group in the molecules.
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M. G. Voronkov, G. I. Sarapulova, N. N. Chipanina, E. N. Medvedeva, T. I. Yushmanova, V. A. Lopyrev, and Yu. L. Frolov, Izv. Akad. Nauk SSSR, Ser. Khim., 2739 (1980).
G. I. Sarapulova, N. N. Chipanina, L. I. Volkova, R. G. Sultangareev, N. A. Khlopenko, V. A. Lopyrev, and Yu. L. Frolov, Izv. Akad. Nauk SSSR, Ser. Khim., 1405 (1982).
N. N. Chipanina, V. A. Lopyrev, G. I. Sarapulova, L. P. Vasil'eva, T. I. Yushmanova, E. N. Medvedeva, and Yu. L. Frolov, Zh. Prikl. Spektrosk.,29, 674 (1978).
E. S. Stern and C. J. Timmons, Gillam and Stern's Introduction to Electronic Absorption Spectroscopy in Organic Chemistry, Edward Arnold, London (1970).
C. D. Schmulbach and R. S. Drago, J. Phys. Chem.,62, 1956 (1960).
M. G. Voronkov, V. V. Dorokhova, E. I. Brodskaya, V. P. Baryshok, and B. I. Vainshtein, Dokl. Akad. Nauk SSSR,250, 1410 (1980).
M. J. Aroney, G. Cleaver, R. K. Pierens, and R. I. W. Le Fe'vre, J. Chem. Soc., Perkin Trans. 2, 1854 (1976).
E. V. Titov, Dissertation, Kiev (1973).
V. M. Vlasov and G. G. Yakobson, Usp. Khim.,13, 1642 (1974).
G. I. Sarapulova, N. N. Chipanina, E. N. Medvedeva, T. I. Yushmanova, V. V. Keiko, V. A. Lopyrev, Yu. L. Frolov, and M. G. Voronkov, Izv. Akad. Nauk SSSR, Ser. Khim., 772 (1981).
L. J. Bellamy, The Infra-Red Spectra of Complex Molecules, Halsted, New York (1975).
A. P. Grekov and V. Ya. Veselov, Physical Chemistry of Hydrazine [in Russian], Naukova Dumka, Kiev (1979), p. 101.
E. N. Gur'yanova, I. P. Gol'dshtein, and I. P. Romm, The Donor-Acceptor Bond [in Russian], Khimiya, Moscow (1973), p. 64.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2255–2259, October, 1984.
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Sarapulova, G.I., Chipanina, N.N., Volkova, L.I. et al. Influence of substituents on IR and UV spectral parameters of 1-methylhydrazides of aromatic acids. Russ Chem Bull 33, 2056–2060 (1984). https://doi.org/10.1007/BF00954081
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DOI: https://doi.org/10.1007/BF00954081