Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Microorganisms
2.3. Synthesis of (Z)-N′-(4-Methoxybenzylidene) Benzohydrazide Ligand
2.4. Synthesis of (Z)-N′-(4-Methoxybenzylidene) Benzo Hydrazide Ni(II) Complex–(Ni(II)-2L)
2.5. Instrumentation
2.6. X-ray Crystallography
2.7. Biological Studies
3. Results and Discussion
3.1. Synthesis Protocols
3.2. Analytical Characterization
3.2.1. Spectral Analysis
3.2.2. Magnetic Moment
3.2.3. Thermal Analysis
3.3. Crystal Structure
3.4. Biological Activities
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Empirical Formula | C30H26NiN4O4 |
---|---|
Formula weight | 565.26 |
Temperature/K | 100(2) |
Crystal system | monoclinic |
Space group | P21/n |
a/Å | 11.6165(9) |
b/Å | 6.4540(5) |
c/Å | 17.9785(14) |
α/° | 90 |
β/° | 106.395(3) |
γ/° | 90 |
Volume/Å3 | 1293.09(17) |
Z | 2 |
Density (calculated)/(g/cm3) | 1.452 |
μ/mm−1 | 0.795 |
F(000) | 588.0 |
Crystal size/mm3 | 0.210 × 0.200 × 0.180 |
Radiation | MoKα (λ = 0.71073) |
2Θ range for data collection/° | 6.74 to 49.998 |
Index ranges | −13 ≤ h ≤ 13, −7 ≤ k ≤ 7, −21 ≤ l ≤ 21 |
Reflections collected | 15,298 |
Independent reflections | 2283 [Rint = 0.0353, Rsigma = 0.0221] |
Data/restraints/parameters | 2283/0/179 |
Goodness-of-fit on F2 | 1.054 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0245, wR2 = 0.0568 |
Final R indexes [all data] | R1 = 0.0290, wR2 = 0.0605 |
Largest diff. peak/hole/e Å−3 | 0.27/−0.25 |
Comp. | Synthesis Strategy | Physical Properties | |||||
---|---|---|---|---|---|---|---|
Methods | Type | Medium | Reaction Time | Color | Melting Point | Yield (%) | |
HL | Method (i) | Reflux | EtOH | 2 hrs | White | 153 ± 3 | 98 |
Method (ii) | Microwave | PEG | 2 min | Light-brown | 152 ± 2 | 79 | |
Method (iii) | Microwave | Water | 20 sec | White | 156 ± 2 | 99 | |
Method (iv) | Stir | Water | 30 sec | White | 156 ± 2; (DTA, 160) | 99 | |
Ni(II)-2L complex | Reflux | DMF | 15 min | Orange crystal | >300; (DTA, 298) | 87 | |
Microwave-assisted synthesis | DMF | 90 sec | Orange microcrystals | >300 | 98 |
Compound | Chemical Formula | MW | Elemental Analysis (wt %); Found (Calculated) | |||
---|---|---|---|---|---|---|
C | H | N | O | |||
HL | C15H14N2O2 | 254.29 | 70.93 (70.85) | 5.62 (5.55) | 11.10 (11.02) | 12.60 (12.58) |
Ni(II)-2L | C30H26N4NiO4 | 565.26 | 64.05 (63.75) | 4.75 (4.64) | 9.94 (9.91) | 11.35 (11.32) |
Compound | Abs (a.u.) | λ (nm) | ɛ (M−1cm−1) | Assignment | μeff (BM) | Geometry |
---|---|---|---|---|---|---|
HL | 0.445 | 243 | 148 | π–π* | - | - |
1.022 | 296 | 341 | π–π* | |||
1.344 | 315 | 448 | n–π* | |||
Ni(II)-2L | 0.445 | 243 | 148 | π–π* | 0 | Square planar |
1.085 | 296 | 362 | π–π* | |||
1.394 | 315 | 465 | n–π* | |||
0.081 | 372 | 27 | LMCT | |||
0.066 | 411 | 22 | LMCT | |||
0.066 | 433 | 22 | 1A1g → 1A2g | |||
0.017 | 574 | 6 | 1A1g → 1B1g |
Comp. | Step | Temp. (°C) | DrTGA max (°C) | DTA Max (°C) | Mass Loss (%) | Evolved Moieties | Residue (%) | ||
---|---|---|---|---|---|---|---|---|---|
Endo | Exo | Obs. | Calc. | ||||||
HL | 1 | 66–108 | 83 | 89 | - | 9.5 | 9.6 | 1.5 H2O, moisture | - |
2 | 250–380 | 341 | 337, 387, 433 | - | 90.5 | 90.4 | 100% ligand | ||
Ni(II)-2L | 1 | 55–296 | 82, 158 | 82, 225 | - | 4.6 | 5.3 | 2(-CH3) | NiC6H6; Obs. 22.8, Calc. 24.1 |
2 | 297–379 | 342 | 340, 372 | - | 42.3 | 42.1 | 2[C7H5NO] | ||
3 | 380–627 | 462 | 425 | multi | 30.4 | 28.3 | C8H4N2O2 |
Bond Lengths | Bond Angles | |||||
---|---|---|---|---|---|---|
Atom | Atom | Length (Å) | Atom | Atom | Atom | Angle (˚) |
Ni1 | O1 | 1.8403(11) | O1 | Ni1 | O11 | 180.0 |
Ni1 | O11 | 1.8403(11) | O1 | Ni1 | N2 | 83.70(5) |
Ni1 | N2 | 1.8703(13) | O11 | Ni1 | N2 | 96.30(5) |
Ni1 | N21 | 1.8703(13) | O1 | Ni1 | N21 | 96.30(5) |
O1 | C7 | 1.3016(19) | O11 | Ni1 | N21 | 83.70(5) |
N1 | N2 | 1.3976(19) | N2 | Ni1 | N21 | 180.0 |
Compound | Minimal Inhibition Concentration (MIC) (µg/mL) | ||||||
---|---|---|---|---|---|---|---|
Bacteria Species | Fungal Species | ||||||
Gram-Positive | Gram-Negative | ||||||
S. aureus | S. pyogenes | E. coli | P. aeruginosa | C. albicans | A. niger | A. clavatus | |
HL | 500 | 250 | 62.5 | 125 | 500 | 1000 | 1000 |
Ni(II)-2L | 125 | 62.5 | 125 | 250 | >1000 | 500 | 500 |
Gentamycin | 0.25 | 0.5 | 0.05 | 1 | - | - | - |
Nystatin | - | - | - | - | 100 | 100 | 100 |
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Al-Qadsy, I.; Al-Odayni, A.-B.; Saeed, W.S.; Alrabie, A.; Al-Adhreai, A.; Al-Faqeeh, L.A.S.; Lama, P.; Alghamdi, A.A.; Farooqui, M. Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex. Crystals 2021, 11, 110. https://doi.org/10.3390/cryst11020110
Al-Qadsy I, Al-Odayni A-B, Saeed WS, Alrabie A, Al-Adhreai A, Al-Faqeeh LAS, Lama P, Alghamdi AA, Farooqui M. Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex. Crystals. 2021; 11(2):110. https://doi.org/10.3390/cryst11020110
Chicago/Turabian StyleAl-Qadsy, Inas, Abdel-Basit Al-Odayni, Waseem Sharaf Saeed, Ali Alrabie, Arwa Al-Adhreai, Lena Ahmed Saleh Al-Faqeeh, Prem Lama, Abdulaziz Ali Alghamdi, and Mazahar Farooqui. 2021. "Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex" Crystals 11, no. 2: 110. https://doi.org/10.3390/cryst11020110
APA StyleAl-Qadsy, I., Al-Odayni, A.-B., Saeed, W. S., Alrabie, A., Al-Adhreai, A., Al-Faqeeh, L. A. S., Lama, P., Alghamdi, A. A., & Farooqui, M. (2021). Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex. Crystals, 11(2), 110. https://doi.org/10.3390/cryst11020110