SHCHERBAKOV et al.
820
(C2=O), 1638 (C=O), 1599, 1572, 1504, 1498 (C=C),
1049, 1012 (C–F). H NMR spectrum, δ, ppm: 4.46 d
(Medicines), Moscow: Novaya Volna, 2002, 14th ed.,
vol. 1, p. 460.
1
3. Li, J., Li, X., and Wang, Sh., J. Mol. Struct., 2012,
vol. 1012, p. 177; Kuznetsova, N.A. and Kaliya, O.L.,
Russ. Chem. Rev., 1992, vol. 61, no. 7, p. 683; Lin, C.-T.,
Shin, J.-H., Chen, C.-L., and Yang, D.-Y., Tetrahedron
Lett., 2005, vol. 46, p. 5033; Lin, S.-L., Kuo, P.-Y., and
Yang, D.-Y., Molecules, 2007, p. 1316; Ghoili, A.,
Dusek, M., Petricek, V., Ben Ayed, T., and Ben
Hassen, R., J. Phys. Chem. Solids, 2014, vol. 75, p. 188;
Xu, Zh., Ding, G., Zhong, G., Xing, G., Li F., Huang, W.,
and Tian, H., Res. Chem. Intermed., 2008, vol. 34,
nos. 2–3, p. 249; Turki, H., Abid, S., El Gharbi, R., and
Fery-Forgues, S., C. R. Chim., 2006, vol. 9, no. 10,
p. 1252; Hazra, P. and Sarkar, N., Chem. Phys. Lett.,
2001, vol. 342, nos. 3–4, p. 303; da Hora Machado, A.E.,
de Miranda, J.A., Guilardi, S., Nicodem, D.E., and
Severino, D., Spectrochim. Acta, Part A, 2003, vol. 59,
no. 2, p. 345.
(2H, CH2C6H5, J = 5.8 Hz), 7.18–7.26 m (5H, C6H5),
7.54 m (1H, 5-H), 10.21 br.s (1H, NH). 19F NMR spec-
trum, δF, ppm: 8.51 m, 9.13 m, 22.02 m (1F each).
Found, %: C 41.88; H 2.59; Cl 7.43; F 11.57; N 3.26.
C17H9ClF3NO4Zn·2H2O. Calculated, %: C 42.09;
H 2.70; Cl 7.31; F 11.75; N 2.89.
Tris(3-benzylcarbamoyl-6,7,8-trifluoro-2-oxo-
2H-chromen-4-olato)(2,2-bipyridine)europium(III)
(IXe). Yield 0.257 g (57%), white powder, mp 238°C.
IR spectrum, ν, cm–1: 3078 (N–H), 1679 (C2=O), 1592
(C=O), 1559, 1495, 1419 (C=C), 1066, 1007 (C–F).
Found, %: C 53.72; H 2.54; F 12.79; N 5.10.
C51H27EuF9N5O12 ·bipy. Calculated, %: C 54.15;
H 2.61; F 12.64; N 5.18.
(3-Benzylcarbamoyl-6,7,8-trifluoro-2-oxo-
2H-chromen-4-olato)(2,2-bipyridine)chlorozinc(II)
hydrate (IXg). Yield 0.455 g (73%), white powder,
mp 288°C. IR spectrum, ν, cm–1: 3259 (O–H), 3106,
3081 (N–H), 1675 (C2=O), 1645 (C=O), 1599, 1552,
4. Liu, X., Cole, J.M., Waddell, P.G., Lin, T.-C., and
McKechnie, S., J. Phys. Chem. C, 2013, vol. 117,
p. 14130; He, P., Wang, H., Zhang, L., Wang, J.,
Jiang, Y., Fan, R., and Chen, D., Opt. Laser Tech., 2012,
vol. 44, p. 341; Anufrik, S.S. and Tarkovsky, V.V.,
J. Appl. Spectrosc., 2010, vol. 77, p. 640.
1
1492, 1417 (C=C), 1022, 1010 (C–F). H NMR spec-
trum, δ, ppm: 4.42 br.s (2H, CH2C6H5), 7.16–7.25 m
(5H, C6H5), 7.52–8.68 m (9H, C10H8N2, 5-H),
10.25 br.s (1H, NH). 19F NMR spectrum, δF, ppm:
8.57 m, 9.23 m, 21.97 m (1F each). Found, %:
C 51. 84; H 2. 72; Cl 5. 76; F 9. 39; N 6. 68.
C17H9ClF3N3O4Zn·bipy·H2O. Calculated, %: C 52.03;
H 3.07; Cl 5.69; F 9.14; N 6.74.
5. Grazul, M. and Budzisz, E., Coord. Chem. Rev., 2009,
vol. 253, nos. 21–22, p. 2588; Creaven, B.S.,
Devereux, M., Karcz, D., Kellett, A., McCann, M.,
Noble, A., and Walsh, M., J. Inorg. Biochem., 2009,
vol. 103, p. 1196; Sathisha, M.P., Shetti, U.N., Revan-
kar, V.K., and Pai, K.S.R., Eur. J. Med. Chem., 2008,
vol. 43, p. 2338; Gudasi, K.B., Patil, M.S., and
Vadavi, R.S., Eur. J. Med. Chem., 2008, vol. 43, p. 2436;
Bagihalli, G.B., Avaji, P.G., Patil, S.A., and Badami, P.S.,
Eur. J. Med. Chem., 2008, vol. 43, no. 11, p. 2639.
This study was performed under financial support
by the Presidium of the Ural Branch of the Russian
Academy of Sciences (project no. 12-P-3-1020) and by
the Program for Support of Young Scientists and Post-
Graduate Students of the Ural Branch of the Russian
Academy of Sciences (project no. 14-3-NP-344).
6. Hanshaw, R.G., Hilkert, S.M., Jiang, H., and Smith, B.D.,
Tetrahedron Lett., 2004, vol. 45, p. 8721; Kostova, I.
and Nikolova, I., Am. J. Pharm. Tox., 2006, vol. 1, no. 2,
p. 30.
The authors thank junior researcher M.S. Valova
(Heterocyclic Compounds Laboratory, Institute of
Organic Synthesis, Ural Branch, Russian Academy of
Sciences) for recording the photoluminescence spectra.
7. Ketata, I., Mechi, L., Ben Ayed, T., Dusek, M., Petri-
cek, V., and Ben Hassen, R., Open J. Inorg. Chem., 2012,
vol. 2, no. 2, p. 33; Manolov, I., Kostova, I., Netzeva, T.,
Konstantinov, S., and Karaivanova, M., Arch. Pharm.,
2000, vol. 333, no. 4, p. 93; Kostova, I., Manolov, I.,
Netzeva, T., Konstantinov, S., and Karaivanova, M., Eur.
J. Med. Chem., 1999, vol. 34, p. 63; Kostova, I., Mano-
lov, I., Netzeva, T., and Karaivanova, M., Arch. Pharm.,
2001, vol. 334, no. 5, p. 157; Karaivanova, M., Mano-
lov, I., Ninassyan, M.L., Danchev, N.D., and Samuro-
va, S.M., Pharmazie, 1994, vol. 49, p. 856; Jevtić, V.V.,
Pešić, M., Radić, G.P., Vuković, N., Sukdolak, S.,
Klisurić, O., Podolski-Renić, A., Tanić, N., and Trifuno-
vić, S.R., J. Mol. Struct., 2013, vol. 1040, p. 216; Rohlí-
ček, J., Ketata, I., Ben Ayed, T., and Ben Hassen, R.,
J. Mol. Struct., 2013, vol. 1051, p. 280.
REFERENCES
1. Kuznetsova, G.A., Prirodnye kumariny i furokumariny
(Natural Coumarins and Furocoumarins), Leningrad:
Nauka, 1967; Egan, D., O’Kennedy, R., Moran, E.,
Cox, D., Prosser, E., and Thornes, D., Drug Met. Rev.,
1990, vol. 22, no. 5, p. 503; Smyth, T., Ramachan-
dran, V.N., and Smyth, W.F., Int. J. Antimicrob. Agents,
2009, vol. 33, no. 5, p. 421.
2. Silverman, R.B., J. Am. Chem. Soc., 1981, vol. 103,
p. 3910; Mashkovskii, M.D., Lekarstvennye sredstva
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 6 2014