Abstract
Two new Mannich bases, 5-methyl-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)phenol (1) and 5-methyl-2-((4-(4-nitrophenyl)piperazin-1-yl)methyl)phenol (2), were prepared and characterized structurally with elemental analysis, IR, UV and NMR spectroscopic techniques as well as single crystal X-ray diffraction. Compound I crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 6.6726(2) A, b = 17.0542(6) A, c = 13.3222(4) A, β = 100.832(1)°, V = 1489.00 (8) A 3 , Z = 4, R 1 = 0.0408, wR 2 = 0.1143. Compound II crystallizes in the monoclinic space P21 with unit cell dimensions a = 5.9519(2) A, b = 17.3315(8) A, c = 15.7237(7) A, β = 90.348(2)°, V = 1621.95(12) A 3 , Z = 4, R 1 = 0.0353, wR 2 = 0.0965. Both compounds have their structures stabilized by hydrogen bonding and π∙∙∙π interactions. KEY WORDS : Mannich base, Piperazine, X-ray diffraction, Hydrogen bonds Bull. Chem. Soc. Ethiop. 2019 , 33(2), 341-348. DOI: https://dx.doi.org/10.4314/bcse.v33i2.14
Highlights
Mannich bases from phenols and acetophenones especially have shown significant corrosion inhibition, anticancer, antimalarial properties in addition to coordination potentials with metal ions of biological interests including biocatalysis [1, 2]
Formaldehyde, 1-(2-pyridyl)piperazine, 1-(4-nitrophenyl)piperazine and m-cresol as well as solvents were purchased from Sigma-Aldrich and used as received
Compounds I and II were readily synthesized through the reaction of 1:1 molar ratio of m-cresol with 1-(2-pyridyl)piperazine and 1-(4-nitrophenyl)piperazine respectively by refluxing in ethanol, in moderately high yields and high purity (Scheme 1)
Summary
Mannich bases from phenols and acetophenones especially have shown significant corrosion inhibition, anticancer, antimalarial properties in addition to coordination potentials with metal ions of biological interests including biocatalysis [1, 2]. Two new Mannich bases, 5-methyl-2-((4-(pyridin-2-yl)piperazin-1-yl)methyl)phenol (1) and 5methyl-2-((4-(4-nitrophenyl)piperazin-1-yl)methyl)phenol (2), were prepared and characterized structurally with elemental analysis, IR, UV and NMR spectroscopic techniques as well as single crystal X-ray diffraction. Compound I crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 6.6726(2) Å, b = 17.0542(6) Å, c = 13.3222(4) Å, β = 100.832(1)°, V = 1489.00 (8) Å3, Z = 4, R1 = 0.0408, wR2 = 0.1143.
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