Share This Article:

New Schiff Bases from 6,6’-Diformyl-2,2’-Bipyridyl with Amines Containing O, S, N and F: Synthesis and Characterization

Full-Text HTML XML Download Download as PDF (Size:551KB) PP. 264-270
DOI: 10.4236/ijoc.2015.54026    3,584 Downloads   4,058 Views   Citations


Eight novel Schiff Bases, from 6,6′-diformyl-2,2′-bipyridyl (1a, 43%)with O, N, S and F containing amines: Thiosemicarbazide (2a, 70%), 4-Ethyl-3-thiosemicabazide (2b, 75%), 4,4-Dimethyl-3-thio-semicarbazide (2c, 75%), S-benzyldithiocarbazide, SBDTC (2d, 80%), (Trifluromethyl) phenylhy-drazine (2e, 80%), 4-Phenyl-3-thiosemcarbazide (2f, 80%), Thiocarbazide (2g, 70%), 2-Amino-thiophenol (2h, 65%), have been synthesized. The conventional method of synthesis of the Schiff bases involves refluxing the reaction mixture containing the diformyls and amines for 1 hour. The solid products that had formed were filtered off using suction filtration. In few reactions, 2 - 3 drops of conc. sulfuric acid were used to obtain high yield. The structures of all eight novel synthesized compounds have fully been characterized by spectroscopic (IR, NMR, MS) methods.

Cite this paper

Razzak, M. , Karim, M. , Hoq, M. and Mirza, A. (2015) New Schiff Bases from 6,6’-Diformyl-2,2’-Bipyridyl with Amines Containing O, S, N and F: Synthesis and Characterization. International Journal of Organic Chemistry, 5, 264-270. doi: 10.4236/ijoc.2015.54026.


[1] Jaman, Z., Karim, M.R., Siddiquee, T.A., Mirza, A.H. and Ali, M.A. (2013) Synthesis of 5-Substituted 2, 9-Dimethyl-1,10-Phenanthroline Dialdehydes and Their Schiff Bases with Sulfur-Containing Amines. International Journal of Organic Chemistry, 3, 214-219.
[2] Siebert, R., Winter, A., Dietzek, B., Schubert, U.S. and Popp, J. (2010) Dual Emission from Highly Conjugated 2,2':6':2"-Terpyridine Complexes—A Potential Route to White Emitters. Macromolecular Rapid Communications, 31, 883-888.
[3] Siebert, R., Winter, A., Schubert, U.S., Dietzek, B. and Popp, J. (2010) Excited-State Planarization as Free Barrierless Motion in a π-Conjugated Terpyridine. The Journal of Physical Chemistry C, 114, 6841-6848.
[4] Siebert, R., Winter, A., Schubert, U.S., Dietzek, B. and Popp, J. (2011) The Molecular Mechanism of Dual Emission in Terpyridine Transition Metal Complexes—Ultrafast Investigations of Photoinduced Dynamics. Physical Chemistry Chemical Physics, 13, 1606-1617.
[5] Binnemans, K., Lenaerts, P., Driesen, K. and Gorller-Walrand, C. (2004) A Luminescent Tris(2-thenoyltrifluoroace- tonato)europium(III) Complex Covalently Linked to a 1,10-Phenanthroline-Functionalised Sol-Gel Glass. Journal of Materials Chemistry, 14, 191-195.
[6] Larsson, K. and Ohrstrom, L. (2004) X-Ray and NMR Study of the Fate of the Co(1,10-phenanthroline-5,6-diketone)33+ Ion in Aqueous Solution: Supramolecular Motifs in the Packing of 1,10-Phenanthroline-5,6-Diketone and 1,10-Phe- nanthroline-5,6-Diol Complexes. Inorganica Chimica Acta, 357, 657-664.
[7] Steed, J.W. and Atwood, J.L. (2000) Supramolecular Chemistry. Wiley, Chichester.
[8] Chow, C.S. and Bogdan, F.M. (1997) A Structural Basis for RNA—Ligand Interactions. Chemical Reviews, 97, 1489-1514.
[9] Sammes, P.G. and Yahioglu, G. (1994) 1,10-Phenanthroline: A Versatile Ligand. Chemical Society Reviews, 23, 327-334.
[10] Balzani, V., Juris, A., Venturi, M., Campagna, S. and Serroni, S. (1996) Luminescent and Redox-Active PolynuclearTransition Metal Complexes. Chemical Reviews, 96, 759-834.
[11] Daniel, S. and Gnana Raj, G.A. (2013) Photoinduced Electron-Transfer Reactions of Tris(4,4'-dinonyl-2,2'-bipyridyl) Ruthenium(II) Cation with Phenolate Ions in Aqueous Acetonitrile. Journal of Chemical and Pharmaceutical Research, 5, 220-227.
[12] Smith, N.A. and Sadler, P.J. (2013) Photoactivatable Metal Com-plexes: From Theory to Applications in Biotechnology and Medicine. Philosophical Transactions of the Royal Society A, 373, Article ID: 20120519.
[13] Monat, J.E., Rodriguez, J.H. and McCusker, J.K. (2002) Ground- and Excited-State Electronic Structures of the Solar Cell Sensitizer Bis(4,4'-dicarboxylato-2,2'bipyridine)bis(isothiocyanato)ruthenium(II). Journal of Physical Chemistry A, 106, 7399-7406.
[14] Gomathi, V., Selvameena, R., Subbalakshmi, R. and Valarmathy, G. (2013) Synthesis, Spectral Characterization and Antimicrobial Screening of Mn(ll) and Zn(ll) Complexes Derived from (E)-1-((p-tolylimino)methyl)naphthalene-2-ol. Oriental Journal of Chemistry, 29, 533-538.
[15] Wang, J., Onions, S., Pilkington, M., Stoeckli-Evans, H., Halfpenny, J.C. and Wallis, J.D. (2007) Metal Catalyzed Rearrangement of a 2,2-Bipyridine Schiff-Base Ligand to a Quaterpyridine-Type Complex. Chemical Communications, 2007, 3628-3630.
[16] Hodacova, J. and Budesmsky, M. (2007) New Synthetic Path to 2,2'-Bipyridine-5,5'-Dicarbaldehyde and Its Use in the [3+3] Cyclocondensation with Trans-1,2-Diaminocyclohexane. Organic Letters, 9, 5641-5643.
[17] Newkome, G.R. and Lee, H.-W. (1983) 18[(2,6) Pyridin6coronand-6: “Sex-ipyridine”. Journal of the American Chemical Society, 105, 5956-5957.
[18] Mughrabi, F.F., Hashim, H., Ameen, M., Khaledi, H. and Ali, H.M. (2011) Cytoprotective Effect of Benzyl N'-(indol- 3-ylmethylidene)-Hydrazinecarbodithioate against Ethanol-Induced Gastric Mucosal Injury in Rats. African Journal of Pure and Applied Chemistry, 5, 34-42. |

comments powered by Disqus

Copyright © 2018 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.