International Journal of Trend in Scientific Research and Development (IJTSRD)

Volume 5 Issue 5, July-August 2021 Available Online: www.ijtsrd.com e-ISSN: 2456 – 6470

Synthesis, IR Spectroscopy and X-Ray Diffraction Analysis

of Copper (II) Complexes Based on 1-Benzoyl-3-Phenyl-5-
Hydroxy-5-Trifluoromethyl-2-Pyrazoline and its Derivatives
Umarov Bako Bafayevich1, Avezov Kuvondik Giyosovich2,
Kholikova Gulyayra Kuldoshevna3, Raufova Madinabonu Mansurovna4
1
Doctor of Chemical Sciences, Professor,
2
PhD of Chemical Sciences, Associate Professor,
3,4
Master`s, Department of Organic and Physcolloidial Chemistry, Faculty of Natural Science,
1,2,3,4
Bukhara State University, Bukhara City, Uzbekistan

ABSTRACT How to cite this paper: Umarov Bako

Mononuclear copper (II) complexes were synthesized on the basis of Bafayevich | Avezov Kuvondik
1-benzoyl-3-phenyl-5-hydroxy-5-trifluoromethyl-2-pyrazoline and its Giyosovich | Kholikova Gulyayra
derivatives [1]. The synthesized complexes are researched with Kuldoshevna | Raufova Madinabonu
application of methods of the element analysis, IR spectroscopy. The Mansurovna "Synthesis, IR
Spectroscopy and X-Ray Diffraction
molecular and crystal structure of a complex of copper (II) with
Analysis of Copper (II) Complexes
benzoylhydrazone of 1,1,1-trifluor-4- (4-bromphenyl)-butane-2,4- Based on 1-Benzoyl-3-Phenyl-5-
dion (H2L5) structure CuL5·NH3 is established by a method X-ray Hydroxy-5-Trifluoromethyl-2-
diffraction analysis. Pyrazoline and its Derivatives"
Published in
KEYWORDS: benzoylhydrazone, aroyltrifluoroacetylmethane, spin-
International
hamiltonian, hyperfine structure, additional hyperfine structure, Journal of Trend in
square structure, crystal structure Scientific Research
and Development
(ijtsrd), ISSN: 2456-
6470, Volume-5 | IJTSRD45052
Issue-5, August
2021, pp.1255-1258, URL:
www.ijtsrd.com/papers/ijtsrd45052.pdf

Copyright © 2021 by author (s) and

International Journal of Trend in
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1. INTRODUCTION
To date, little time and attention has been devoted to reasonable conclusions and predict the ways of
the study of the geometric and electronic structure of directed synthesis of complex compounds with
complex copper (II) compounds with ligands such as specified properties [4-6, 9].
acylhydrazones of fluorinated β-dicarbonyl We synthesized complex compounds of copper (II)
compounds [1-3, 5, 12-17]. Meanwhile, the study of with benzoylhydrazones of
the magnetic properties of copper-containing aroyltrifluoroacetylmethanes. The results of elemental
complexes, along with the consideration of their analysis and spectroscopic studies allowed us to
geometric and electronic structure, allows us to draw attribute CuL·NH3 to the compounds:

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 International Journal of Trend in Scientific Research and Development @ www.ijtsrd.com eISSN: 2456-6470
4X-C6H4 4X-C6H4 CF3
C CH2
CF3 Cu(CH3COO)2
N O
N C N
OH
N Cu
C C6H5 O NH3
C6H5 O
X = H (CuL1·NH3); CH3 (CuL2·NH3); OCH3 (CuL3·NH3); Cl (CuL4·NH3); Br (CuL5·NH3).
2. EXPERIMENTAL PART
Synthesis of CuL1·NH3. To a hot solution of 0.5 g (0.0015 mol) of 1-benzoyl-3-phenyl-5-hydroxy-5-
trifluoromethyl-2-pyrazoline (H2L1) in 25 ml of ethanol, an aqueous-ammonic solution of 0.0015 mol (0.30 g) of
copper (II) acetate in 15 ml of 25% ammonia solution was added. The reaction flask was heated with a reverse
refrigerator for 30 minutes. After 2 days, the green precipitate was filtered out, washed with water, ethanol and
dried in the air. Output of the CuL1 complex.NH3 was 0.46 g (72 %) with T. sol. 223 oC.
Other copper (II) complexes have been synthesized similarly. The outputs and data of the elemental analysis of
complex copper (II) compounds are given in table 1.
Table 1 Yields, melting points, and results of elemental analysis of copper (II) Cu·NH3 complexes
based on benzoylhydrazones of aroyltrifluoroacetylmethanes
Yield, Tsol., Brutto- Found/ Calculated, %
Compound о
% С formula Cu С Н N
CuL1·NH3 72 223 CuC17H14F3N3O2 15,34/15,39 49,41/49,46 3,40/3,42 10,22/10,18
CuL2·NH3 65 256 CuC18H16F3N3O2 14,83/14,89 50,60/50,64 3,75/3,78 9,87/9,84
3
CuL ·NH3 79 233 CuC18H16F3N3O3 14,30/14,35 48,77/48,82 3,61/3,64 9,51/9,49
CuL4·NH3 86 247 CuC17H13ClF3N3O2 14,18/14,21 45,62/45,65 2,89/2,93 9,42/9,39
CuL5·NH3 36 * CuC17H13ВrF3N3O2 12,88/12,92 41,49/41,52 2,64/2,66 8,57/8,55
Single crystals of CuL5⋅NH3 were grown during recrystallization of the complex from ethanol. X-ray diffraction
was performed using an automatic Xcalibur diffractometer (CuKa radiation, λ=1.54 Å, graphite monochromator,
ω scanning, 2θmax= 50°).
3. RESULT AND DISCUSSIONS
3.1. IR spectroscopy
In the IR spectrum of the CuL5·NH3 complex (Fig. 1., Table 2.), the vibrational frequency ν (C=N) (1607 sm−1) is
compared to the IR spectrum of the free ligand (the absorption band ν (C=N)= 1633 sm−1) shifted to the low
frequency region by 26 sm−1. This suggests the coordination of the ligand to the metal via two amide and β –
diketone oxygen atoms and an azomethine nitrogen atom [4, 7-13, 15].

Figure 1 IR spectrum of a complex copper (II) compound CuL5·NH3 based on benzoyl hydrazone
1,1,1-trifluoro4 - (4-bromophenyl)- butane-2,4-dione (H2L5).

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Table 2 Parameters of IR spectra of copper (II) complex compounds based on benzoylhydrazones of
aroyltrifluoroacetylmethanes
Соединение NH3 C–H C=N N=C–C=N N=C–O– N–N Cu–O
CuL1·NH3 3359 2976 1604 1526 1495 1065 485
2
CuL ·NH3 3362 2973 1605 1528 1497 1072 489
CuL3·NH3 3357 2975 1607 1527 1494 1073 486
4
CuL ·NH3 3356 2977 1608 1528 1498 1075 488
CuL5·NH3 3357 2976 1607 1529 1496 1078 490
3.2. X-ray diffraction anaysis
Conclusions about the planar structure of the complex with tridentate coordination of the ligand dianion (Ln)2–,
based on the results of IR spectra and the X-ray diffraction method for the CuL5·NH3 complex grown single
crystal.
C17H13BrF3N3O2Cu crystals, triclinic, a=9,7929 (13), b = 12,5906 (20), c = 15,6732 (16) Å, α = 86,427 (10)°, β
= 84,771 (10)°, γ = 69,602 (13)°, V= 1802,8 Å3, ρ (h) = 1,812 g/sm3, Z = 4, etc. gr. P-1. The complex molecule
contains almost flat articulated five-and six-membered metallocycle (Fig. 3.). The doubly deprotonated residue
of the H2L5 molecule is coordinated by a copper atom through two oxygen atoms and a nitrogen atom of the
hydrazone fragment. The fourth place in the flat square of the trans-N2О2 coordination node is occupied by the
nitrogen atom of the ammonia molecule [17-19].

Figure 3 Molecular structure and packaging of CuL5.NH3 molecules.

4. Conclusion on acylhydrazones of aroyl-
Thus, as a result of studies using IR spectroscopy and trifluoroacetylmethanes. Materials of the XIII
X - ray diffraction, it was found that the interaction of International Scientific Conference of young
Cu (II) ions with benzoylhydrazones of scientists "Innovative development and demand
aroyltrifluoroacetylmethanes, which exhibit the for science in modern Kazakhstan" II vol.
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metal cycles of a flat-square structure. green synthesis and antioxidant activities of
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