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Synthesis of N,N'-bis (a-methylsalicylidene) 4,4'-diaminodiphenylmethane as a novel complexing agent

Department of Chemistry, College of Sciences, Shiraz University,Shiraz 71454, Iran
Author to whom correspondence should be addressed.
Molbank 2006, 2006(1), M456;
Submission received: 8 October 2005 / Accepted: 25 November 2005 / Published: 22 January 2006
Schiff base ligands are used in complexation with metals such as V(II) for the enantioselective oxidation of sulfides to chiral sulfoxides.An increasing number of chiral sulfoxides are becoming useful chiral auxiliaries in asymmetric synthesis [1].Cameron and his co-workers have shown that Schiff base ligands are capable of stabilising cationic methylaluminium centres only when they possess an additional donor arm [2].Synthesis and spectroscopic studies of the optically active copper(II), cobalt(II) and nickel(II) complexes with Schiff bases have been studied by Szlyk [3].Schiff base ligands have been used in several catalytic asymmetric reactions [4]. Metal complex Schiff bases have also been used in oxidation reactions [5].
Molbank 2006 m456 i001
2-Hydroxyacetophenone 1 (2.03g, 1.8 mL, 15.00 mmol) and 4,4′-diaminodiphenylmethan 2 (0.99 g, 5.00 mmol) were dissolved in 10 mL of warm ethanol. The reaction mixture was refluxed for 14h.The solid product was filtered off and washed with ethanol. The pure Schiff base 3 was obtained as a yellow solid (yield 78%)
Melting Point: 120°C
IR (KBr, ν, cm-1): 3244 (OH); 1647 (C=N).
1H-NMR (250 MHz, CDCl3): δ= 2.20 (6H, s, ArCH3); 3.87(2H, s, Ar-CH2); 6.61 (2H, d, Ar); 7.06-7.96 (5H, m, Ar); 14.86 (2H, s, OH).
13C-NMR (62.9 MHz, CDCl3): δ= 17.06; 40.88; 11.35; 11.24; 12.57; 128.89; 129.52; 129.76; 132.96; 137.67; 138.64; 162.07; 171.24.
MS (m/z): 434 (25%), 316 (37%), 198 (38%), 106 (87%), 77 (20%).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3


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


  1. Gama, A.; Flores-López, L. Z.; Aguirre, G.; Hellberg, M. P. H.; Somanathan, R. Arkivoc 2003, 4–15.
  2. Cameron, P. A.; Gibson, V. C.; Redshaw, C.; Segal, J. A.; Bruce, M. D.; White, A.; Williams, D. Chem. Commun. 1999, 1883–1884.
  3. Szłyk, E.; Barwiołek, M.; Kruszynski, R.; Bartczak, T. Inorg. Chim. Acta 2005, 358, 3642–3652.
  4. Flores-lopez, L. Z.; Parra-Hake, M. P.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153–2160.
  5. Kervinen, K.; Korpi, H.; Leskela, M.; Repo, T. J. Mol. Cat. 2003, 203, 9–19.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Jarrahpour, A.A.; Rezaei, S. Synthesis of N,N'-bis (a-methylsalicylidene) 4,4'-diaminodiphenylmethane as a novel complexing agent. Molbank 2006, 2006, M456.

AMA Style

Jarrahpour AA, Rezaei S. Synthesis of N,N'-bis (a-methylsalicylidene) 4,4'-diaminodiphenylmethane as a novel complexing agent. Molbank. 2006; 2006(1):M456.

Chicago/Turabian Style

Jarrahpour, A. A., and S. Rezaei. 2006. "Synthesis of N,N'-bis (a-methylsalicylidene) 4,4'-diaminodiphenylmethane as a novel complexing agent" Molbank 2006, no. 1: M456.

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