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. 2022 Jun 5;8(6):e09650.
doi: 10.1016/j.heliyon.2022.e09650. eCollection 2022 Jun.

Synthesis, spectral studies, antioxidant and antibacterial evaluation of aromatic nitro and halogenated tetradentate Schiff bases

Bhagwat Vhanale  1 , Digambar Kadam  2 , Avinash Shinde  3
Affiliations

Synthesis, spectral studies, antioxidant and antibacterial evaluation of aromatic nitro and halogenated tetradentate Schiff bases

Bhagwat Vhanale et al. Heliyon. .

Abstract

Herein, we report the synthesis, characterization, and biological properties of eleven (3a-3k) novel Schiff bases. The spectral data of FT-IR, 1H NMR, 13C NMR, and LC-MS are associated with these synthesized compounds. From the FT-IR analysis, we confirmed the azomethine (-C=N-) group and from 1H NMR data, the phenolic -OH proton is appeared at range δ 13.92-14.09ppm due to hydrogen bonding. The LC-MS analysis agreed with molecular ion peaks of synthesized Schiff bases. To evaluate the antibacterial activity of newly synthesized compounds were screened against b. licheniformis, b. species, e. coli, and s. aureus. Furthermore, the antioxidant activity was investigated by two methods 2,2-diphenyl-1-picryl hydrazyl (DPPH) and hydroxyl radical scavenging methods. The (-NO2,-Cl,-Br,-I) substituted compounds have shown good antibacterial activity against tested organisms. Also, these compounds were exhibited higher antioxidant activity by given methods.

Keywords: 1-hydroxy-2-acetonapthanone; 1H NMR; Antimicrobial activity; Mass spectrometry; Primary diamines.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Image 1
Graphical abstract
Scheme 1
Scheme 1
Synthesis of Schiff Bases (3a-3k). 1a. R = -H, 1b. R = -Cl, 1c. R = -Br, 1d. R = -I, 1e. R = -NO2. 2a. R’= -CH2-CH2-, 2b. R’= -CH2-CH2-CH2-, 2c. R’ = -CH(C2H5)-CH2-CH2-. 3a. R = -H, R’ = -CH2-CH2-, 3b. R = -Cl, R’= -CH2-CH2-, 3c. R = -Br, R’ = -CH2-CH2-, 3d. R = -I, R’ = -CH2-CH2-, 3e. R = -NO2, R’ = -CH2-CH2-, 3f. R = -Br, R’= -CH2-CH2-CH2-, 3g. R = -I, R’ = -CH2-CH2-CH2-, 3h. R = -NO2, R’ = -CH2-CH2-CH2-, 3i. R = -Cl, R’ = -CH(C2H5)-CH2-CH2-, 3j. R = -I, R’ = -CH(C2H5)-CH2-CH2-, 3k. R = -NO2, R’ = -CH(C2H5)-CH2-CH2-.
Figure 1
Figure 1
Antibacterial activity of Schiff bases (3a-3k) against gram positive and gram negative error bars represents the standard deviation of triplicate measurements.
Figure 2
Figure 2
Antioxidant activity of Schiff bases (3a-3k) error bars represents the standard deviation of triplicate measurements.
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