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Synthesis of N,N'-bis (a-methylsalicylidene)-3,4'-diaminodiphenyl ether

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
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Author to whom correspondence should be addressed.
Molbank 2006, 2006(1), M458; https://doi.org/10.3390/M458
Received: 21 September 2005 / Accepted: 15 January 2006 / Published: 22 January 2006
Keywords: 2-Hydroxyacetophenone; 3; 4'- diaminodiphenyl ether; Schiff base 2-Hydroxyacetophenone; 3; 4'- diaminodiphenyl ether; Schiff base
There have been few reports about the synthesis and application of Schiff-base ligands derived from 2-hydroxyacetophenone [1]. In order to investigate the electronic, steric and geometric effect of a methyl group on an imine carbon on asymmetric catalytic reactions, 2-hydroxyacetophenone (1) has been chosen as starting material for synthesizing Schiff-base ligands [2]. Suhai and his coworkers have studied the conformational effects on the proton affinity of the Schiff base in bacteriorhodopsin [3]. Jacobsen and his coworkers have studied about asymmetric catalysis of hetero-ene reaction with tridentate Schiff base Cr(III) complexes[4].
Molbank 2006 m458 i001
2-Hydroxyacetophenone 1 (0.272 g, 0.24 mL, 2 mmol) and 3,4'-diaminodiphenylether 2 (0.33 g, 1 mmol) were dissolved in 10 mL of warm ethanol. The reaction mixture was refluxed for 10h and allowed to stand aside.The solid crystals were filtered off and washed with ethanol.The pure Schiff base 3 was isolated as a light yellow crystalline solid (yield 78%).
Melting Point: 182-184 °C
IR (KBr, ν, cm-1): 3244(OH), 1620(C=N).
1H-NMR (250 MHz, CDCl3): δ= 1.65(6H, s, CH3), 6.21(2H, d, Ar), 6.24(2H, d, Ar), 6.88-7.64(5H, m, Ar), 7.94(2H, d, Ar), 14.57(2H, s, OH).
13C-NMR (62.9 MHz, CDCl3): δ= 17.22; 111.71; 113.20; 118.22; 119.63; 126.66; 128.88; 132.95;142.73; 145.60; 146.60; 162.15; 171.23.
MS (m/z): 436 (87%), 317 (40%), 210 (48%), 139 (38%), 91 (90%).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No.84-GR-SC-23)

References

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  2. Gao, W. T.; Zheng, Z. Molecules 2002, 7, 511–516.
  3. Tajkhorshid, E.; Paizs, B.; Suhai, S. J. Phys. Chem 1997, 101, 8021–8027.
  4. Ruck, R. T.; Jacobsen, E. J. J. Am. Chem. Soc. 2002, 124, 2882–2883.
  • Sample Availability: Available from MDPI.
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