Abstract
4-(Piperidyl-1)-2-phenylpyrido[2,3-a]anthraquinone-7,12 monobromohydrate (HL)Br · 3H2O (I) and 4-(piperidyl-1)-2-phenylpyrido[2,3-a]anthraquinone-7,12 dibromohydrate (H2 L)Br2 · 3H2O (II) are isolated in the crystalline state. The crystal structures of compounds I and II are determined using X-ray diffraction. It is established that the protonation of 4-(piperidyl-1)-2-phenylpyrido[2,3-a]anthraquinone-7,12 proceeds primarily through the pyridine atom at pH 2–3. The attachment of the second proton occurs through the piperidine nitrogen atom at pH ∼ 1.
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References
B. I. Stepanov, An Introduction to the Chemistry and Technology of Organic Dyes (Khimiya, Moscow, 1984) [in Russian].
V. Ya. Faĭn, 9,10-Anthraquinones and Their Application (Photochemistry Center, Russian Academy of Sciences, Moscow, 1999) [in Russian].
V. Ya. Faĭn, Electronic Absorption Spectra and the Structure of 9,10-Anthraquinones (Sputnik+, Moscow, 2003), Vol. 1 [in Russian].
R. A. Muzychkina, Natural Anthraquinones: Biological Properties and Physicochemical Characteristics (Fazis, Moscow, 1998) [in Russian].
S. B. Strashnova, B. E. Zaitsev, V. E. Zavodnik, O. V. Kovalchukova, and D. P. Voronin, Koord. Khim. 33(11), 864 (2007) [Russ. J. Coord. Chem. 33 (11), 850 (2007)].
V. V. Davydov, M. G. Sarabiya, A. I. Ezhov, et al., Koord. Khim. 20(10), 803 (1994).
G. M. Sheldrick, SHELX97: Program for the Solution and Refinement of Crystal Structures (University of Göttingen, Göttingen, Germany, 1997).
O. V. Kovalchukova, A. I. Stash, S. B. Strashnova, V. K. Belsky, Tran Than Tung, and B. E. Zaĭtsev, Kristallografiya 53(2), 270 (2008) [Crystallogr. Rep. 53 (3), 451 (2008)].
V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev, Theory of Molecular Structure (Feniks, Rostov-on-Don, 1977) [in Russian].
M. Dewar, The Molecular Orbital Theory of Organic Chemistry (McGraw-Hill, New York, 1969; Mir, Moscow, 1973).
N. E. Kuz’mina, K. K. Palkina, N. V. Polyakova, I. N. Golubev, A. N. Medvedev, O. V. Koval’chukova, S. B. Strashnova, B. E. Zaitsev, A. N. Levov, and F. Toze, Zh. Neorg. Khim. 47(11), 1843 (2002) [Russ. J. Inorg. Chem. 47 (11), 1693 (2002)].
N. E. Kuz’mina, K. K. Palkina, N. V. Polyakova, I. N. Golubev, A. N. Medvedev, O. V. Koval’chukova, S. B. Strashnova, N. I. Mordovina, S. V. Nikitin, and B. E. Zaitsev, Zh. Neorg. Khim. 48(2), 257 (2003) [Russ. J. Inorg. Chem. 48 (2), 205 (2003)].
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Original Russian Text © O.V. Kovalchukova, A.I. Stash, V.K. Belsky, S.B. Strashnova, B.E. Zaĭtsev, M.A. Ryabov, 2009, published in Kristallografiya, 2009, Vol. 54, No. 1, pp. 72–76.
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Kovalchukova, O.V., Stash, A.I., Belsky, V.K. et al. Synthesis and the crystal and molecular structures of 4-(piperidyl-1)-2-phenylpyrido[2,3-a]anthraquinone-7,12 Mono- and dibromohydrates (HL)Br · 3H2O and (H2 L)Br2 · 3H2O. Crystallogr. Rep. 54, 68–73 (2009). https://doi.org/10.1134/S106377450901012X
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DOI: https://doi.org/10.1134/S106377450901012X