Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone
Abstract
:1. Introduction
2. Results and Discussion
2.1. Characterization of the Ligand
Compound | F.W. | Color | Yield(%) | M.P. (°C) | Elemental analysis, Found / (Calcd) % | Solubility | ||||
---|---|---|---|---|---|---|---|---|---|---|
C | H | N | CL | M | ||||||
C17H14N3OCl (HL) | 311.5 | Deep Orange | 66 | 225 | 65.37 (65.49) | 4.39 (4.49) | 13.48 (13.48) | 11.30 (11.4) | -- | Soluble in most common organic solvent |
[(HL)2Cu].EtOH (1) C36H32N6O3Cl2Cu | 731 | Green | 33 | 287 | 59.00 (59.10) | 4.27 (4.38) | 11.29 (11.49) | 9.51 (9.71) | 8.66 (8.76) | Soluble in acetone and insoluble in methanol and ethanol |
[Ni (HL)2(OH2)2] 2EtOH (2) C28H42N6O6Cl2Ni | 808 | Pale Green | 25 | 220 | 56.24 (56.44) | 5.13 (5.20) | 10.40 (10.40) | 8.79 (8.79) | 7.30 (7.30) | Soluble in most common organic solvent |
[(L)2Ni2(OH2)6]a (3) C34H36N6O8Cl2Ni2 | 845 | Yellowish Green | 47 | 250 (decomp) | 48.15 (48.28) | 4.07 (4.26) | 9.75 (9.94) | 8.08 (8.28) | 13.67 (13.96) | Soluble in acetone and insoluble in methanol and ethanol |
[(L)2Co2(OH2)6]a (4) C34H36N6O8Cl2Co2 | 845 | Brown | 34 | 260 (decomp) | 48.00 (48.18) | 4.50 (4.28) | 10.12 (9.99) | 8.07 (8.26) | 13.79 (13.98) | Soluble in most common organic solvent except diethyl ether |
[(L)2Mn(OH2)6]a (5) C34H36N6O8Cl2Mn2 | 837 | Deep brown | 48 | 225 | 49.00 (48.75) | 4.50 (4.30) | 9.10 (10.04) | 8.27 (8.36) | 12.97 (13.14) | Soluble in acetone and insoluble in methanol and ethanol and ether |
[(HL)2UO2(EtOH)] (6) C36H32N6O5Cl2U | 937 | Red | 75 | 225 (decomp) | 46.31 (46.10) | 3.51 (3.42) | 9.21 (8.96) | 7.73 (7.58) | 25.20 (25.40) | Soluble in most common organic solvent except diethylether |
[(L)2Fe2Cl2(OH2)4] 2EtOHa (7) C38H44N6O8Cl4Fe2 | 966 | Reddish brown | 55 | 250 (decomp) | 47.35 (47.20) | 4.26 (4.55) | 8.58 (8.70) | 14.52 (14.70) | 11.45 (11.59) | Soluble in most common organic solvent except diethylether |
Chemical shift, δTMS (ppm) | Assignment a |
---|---|
14.5 | [s, 1H] (1) |
2.4 | [s, 3H] (2) |
11.7 | [s, 1H] (3) |
7.9–8.3 | [m, 9H, Ar–H and quinoline–H] |
Compound | ν(C=N) | ν(N-H) | ν(N-N) | ν(M-N) | ν(M-O) | ν(OH), H2O or alcohol | Other bands |
---|---|---|---|---|---|---|---|
HL | 1524 s | 3300 m | 1140s | --- | --- | 3530m, br (νOH-phenolic) | 1278 (δ OH-phenolic) |
[(HL)2Cu] EtOH (1) | 1520 s | 3215 m | 1136 s | 420 w | 540 m | 3426 m, br (νOH-alcohol | --- |
[(HL)2Ni(OH 2)2] 2EtOH (2) | 1510 m | 3200 s | 1137 w | 425 w | 520 m | 3440 m, br (νOH-coordinated water over-lapped with (νOH- alcohol | --- |
[(L)2Ni2(OH2)6] (3) | 1514 sh | --- | 1125 w | 410 w | 515 m | 3436 m, br (νOH-coordinated water | --- |
[(L)2Co2(OH)2)6] (4) | 1527 sh | --- | 1136 S | 445W | 520W | 3438 m, br (νOH-coordinated water | --- |
[(L)2Mn(OH2)6] (5) | 1507 m | --- | 1137 s | 465 w | 520 m | 3439 m, br (νOH-coordinated water | --- |
[(HL)2UO2(EtOH)] (6) | 1505 | 3214 sh | 1134 s | 460 w | 540 w | 3435 m, br (νOH-coordinated water over-lapped with (νOH-coordinated alcohol | 901 s ν3(O=U=O |
[(L)2Fe2Cl2(OH2)4] 2EtOH (7) | 1515 s | --- | 1138 W | 460 W | 515 W | 3435 m, br (νOH-coordinated water overlapped with (νOH- alcohol | --- |
Compound | μeff.b B.M. | μcomble c found (expected d)B.M. | *π→π, n→π* and charge transfer transitions | d→dTransition(cm−1) | EC f |
---|---|---|---|---|---|
HL | --- | --- | 48067, 44642, 36231, 26176,24752 | --- | --- |
[(HL)2Cu] EtOH (1) | 1.807 | 1.807 | 36765 ,28612, 22396 | 15850 | 2.4 |
[HL)2Ni(OH 2)2] 2EtOH (2) | 2.85 | 2.85 | 37037, 28653, 22371 | 15850 | 2.0 |
[(L)2Ni2(OH2)6] (3) | --- | 4.44 (5.71) | 37437, 28670,22300 | 1518.45, 11957 | 2.6 |
[(L)2Co2(OH)2)6] (4) | --- | 7.12 1(10.4) | 370307, 28600, 22271 | 15250, 15390 | 2.4 |
[(L)2Mn(OH2)6] (5) | --- | 5.39 (8.40) | 37085, 28500, 22471 | 21331.9, 11733.33 | 3.6 |
[(HL)2UO2(EtOH)] (6) | --- | --- | 37537, 27853, 22871 | 22500, 19040 | 1.5 |
[(L)2Fe2Cl2(OH2)4] 2EtOH (7) | --- | 7.49 (10.80) | 37137, 27653, 22571 | 14331, 13850 | 68 |
2.2. Metal Complexes
2.3. IR Spectra of the Metal Complexes
2.4. Magnetic Moments and Electronic Spectral Data of the Metal Complexes
2.5. Molar Conductance of the Metal Complexes
2.6. 1H-NMR Spectrum of the Uranyl Complex
- (1). The disappearance of the signal due to the phenolic OH group is attributed to its involvement in coordinating the uranylcation, While the signal due to the NH group was broad and appeared at δ = 12.4 ppm compared to that of the ligand which appeared at, δ =11.7 ppm, i.e., shifted to low-field.
- (2). The signals due to the aromatic ring showed fine structure and appear as four separate signals at δ = 7.14, 7.53 and 7.6 ppm.
- (3). The NH group which did not take part in coordinating the uranylcation disappeared on deuteration.
- (4). The CH3 group signal remained unchanged as observed in the parent ligand.
2.7. Antimicrobial Activity and Minimum Inhibitory Concentration (MIC)
Compound | Conc.% | Micro-organism | ||
---|---|---|---|---|
S. aureus ATCC * 6538MIC *** 25% | E. coli ATCC 8739 MIC 25% | C. albicans ATCC 10231MIC 25% | ||
o-Hydroxyacetophenone-7-chloro-4-quinoline hydrazine (HL) | 1 ** | |||
25 | +ve | −ve | +ve | |
50 | +ve | −ve | +ve | |
100 | +ve | +ve | +ve | |
[(HL)2Cu] EtOH (1) | 1 | +ve | +ve | +ve |
25 | +ve | +ve | +ve | |
50 | +ve | +ve | −ve | |
100 | −ve | −ve | −ve | |
[HL)2Ni(OH2)2] 2EtOH (2) | 1 | +ve | −ve | −ve |
25 | +ve | +ve | +ve | |
50 | +ve | +ve | +ve | |
100 | −ve | −ve | −ve | |
[(L)2Ni2(OH2)6] (3) | 1 ** | |||
25 | −ve | +ve | −ve | |
50 | −ve | −ve | −ve | |
100 | −ve | −ve | −ve | |
[(L)2Co2(OH2)6] (4) | 1 | +ve | +ve | +ve |
25 | −ve | +ve | −ve | |
50 | −ve | −ve | −ve | |
100 | −ve | −ve | −ve | |
[(L)2Mn(OH2)6] (5) | 1 ** | |||
25 | −ve | +ve | −ve | |
50 | −ve | −ve | −ve | |
100 | −ve | −ve | −ve | |
[(HL)2UO2(EtOH)] (6) | 1 | +ve | +ve | +ve |
25 | −ve | +ve | −ve | |
50 | −ve | +ve | −ve | |
100 | −ve | −ve | −ve | |
[(L)2Fe2Cl2(OH2)4].2EtOH (7) | 1 | +ve | +ve | +ve |
25 | −ve | +ve | −ve | |
50 | −ve | −ve | −ve | |
100 | −ve | −ve | −ve | |
7-Chloro-4-hydrazinoquinoline | 1 | +ve | +ve | +ve |
25 | −ve | −ve | −ve | |
50 | −ve | −ve | −ve | |
100 | −ve | −ve | −ve |
3. Experimental
3.1. General
3.2. Synthesis of the Schiff Base Hydrazone Ligand (HL)
3.2.1. Synthesis of 7-Chloro-4-hydrazinoquinoline
3.2.2. Synthesis of the ligand HL
3.3. Synthesis of the Metal Complexes
3.3.1. Cu(II) Complex, [(HL)2Cu] EtOH
3.3.2. Ni(II) Complexes
3.3.2.1. In the Absence of LiOH, [(HL)2Ni(OH2)2] 2EtOH
3.3.2.2. In the Presence of LiOH, [(L)2Ni(OH2)6]
3.3.3. Co(II) Complex, [[(L)2CO2(OH2)6]
3.3.4. Mn(II)Complex, [(L)2Mn2(OH2)6]
3.3.5. UO2(VI) Complex, [(HL)2UO2(EtOH)]
3.3.6. Fe(III) Complex, [(L)2Fe2Cl2(OH)4] EtOH
3.4. Synthesis of Samples for Microbiological Analysis
3.5. Physical Measurements and Analysis
3.6. Pharmacology
4. Conclusions
- Samples Availability: Samples are available from the author.
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Al-Shaalan, N.H. Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone. Molecules 2011, 16, 8629-8645. https://doi.org/10.3390/molecules16108629
Al-Shaalan NH. Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone. Molecules. 2011; 16(10):8629-8645. https://doi.org/10.3390/molecules16108629
Chicago/Turabian StyleAl-Shaalan, Nora H. 2011. "Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone" Molecules 16, no. 10: 8629-8645. https://doi.org/10.3390/molecules16108629