IJOC  Vol.2 No.1 , March 2012
Unusual Catalytic Process Involving OH and NH Exchange
ABSTRACT
Interaction of some transition metals species with a Schiff base, 1, derived from 4,6-diacetylresorcinol and 2-amino- 5-methylphenol (1:2 mole ratio) yielded the two compounds 4-ethanimidoyl-6-[(1E)-N-(2-hydroxy-4-methylphenyl) ethanimidoyl]benzene-1,3-diol, 2, and 4,6-diacetyl-1,3-diaminobenzene, 4 via unusual catalytic process involving OH and NH exchange. All the compounds are characterized by elemental analysis, IR, mass and 1H NMR. The structure of the two compounds 2 and 4 are also determined by X-ray analysis. The crystal structure analysis revealed that the two compounds crystallized in the monoclinic space group P21/c with a Z value of 4.

Cite this paper
R. M. Ramadan and A. K. Abu Al-Nasr, "Unusual Catalytic Process Involving OH and NH Exchange," International Journal of Organic Chemistry, Vol. 2 No. 1, 2012, pp. 64-70. doi: 10.4236/ijoc.2012.21011.
References
[1]   S. J. Archibald, “Coordination Chemistry of Macrocyclic Ligands,” Annual Reports Section A (Inorganic Chemistry), Vol. 105, 2009, pp. 297-322. doi:10.1039/b818281g

[2]   Z. Chu, W. Huang, L. Wang and S. Gou, “Chiral 27-Membered [3 + 3] Schiff-Base Macrocycles and Their Reactivity with First-Row Transition Metal Ions,” Polyhedron, Vol. 27, No. 3, 2008, pp. 1079-1092. doi:10.1016/j.poly.2007.12.003

[3]   T. Dudev and C. Lim, “Tetrahedral vs Octahedral Zn2+ Complexes with Ligands of Biological Interest: A DFT/CDM Study,” Journal of the American Chemical Society, Vol. 122, No. 45, 2000, pp. 11146-11153. doi:10.1021/ja0010296

[4]   T. Dudev and C. Lim, “Modeling Zn2+-Cysteinate Complexes in Proteins,” The Journal of Physical Chemistry, Vol. 105, No. 43, 2001, pp. 10709-10714. doi:10.1021/jp012090f

[5]   S. S. David and E. Meggers, “Inorganic Chemical Biology: From Small Metal Complexes in Biological Systems to Metallo-Proteins,” Current Opinion in Chemical Biology, Vol. 12, 2008, pp. 194-197. doi:10.1016/j.cbpa.2008.03.008

[6]   S. J. S. Flora and V. Pachauri, “Chelation in Metal Intoxication,” International Journal of Environmental Research and Public Health, Vol. 7, 2010, pp. 2745-2788. doi:10.3390/ijerph7072745

[7]   B. Mabad, P. Cassoux, J. P. Tuchagues and D. N. Hendrickson, “Manganese(II) Complexes of Polydentate Schiff Bases. 1. Synthesis, Characterization, Magnetic Properties, and Molecular Structure,” Inorganic Chemistry, Vol. 25, No. 9, 1986, pp. 1420-1431. doi:10.1021/ic00229a025

[8]   D. N. Marks, W. Siegl and R. R. Gagne, “Synthesis and Characterization of Mononuclear and Binuclear Ruthenium Complexes of 1,3-Bis(2-pyridylimino)isoindolines,” Inorganic Chemistry, Vol. 21, No. 8, 1982, pp. 3140-3147. doi:10.1021/ic00138a044

[9]   L. T. Bozic, E. Marotta and P. Traldi, “Efficient Solid-State Microwave-Promoted Complexation of a Mixed Dioxa-Diaza Macrocycle with an Alkali Salt. Synthesis of a Sodium Ethyl 4-Benzeneazophosphonate Complex,” Polyhedron, Vol. 26, No. 8, 2007, pp. 1663-1668. doi:10.1016/j.poly.2006.12.012

[10]   A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, “SIR92—A Program for Automatic Solution of Crystal Structures by Direct Methods,” Journal of Applied Crystallography, Vol. 27, 1994, p. 435.

[11]   S. Mackay, C. J. Gilmore, C. Edwards, N. Stewart and K. Shankland, “Maxus Computer Program for the Solution and Refinement of Crystal Structures,” Nonius, Mac-Science, 1999.

[12]   R. M. Silverstein, G. C. Bassler and T. C. Morrill, “Spectrometric Identification of Organic Compounds,” 4th Edition, Wiley, New York, 1991.

[13]   M. A. Taher, S. E. Jarelnabbi, B. E. Bayoumi, S. M. El-Medani and R. M. Ramadan, “Synthesis and Spectroscopic Studies of Some New Molybdenum, Tungsten and Ruthenium Carbonyl Derivatives of 2-Hydroxy-methylpyridine,” International Journal of Inorganic Chemistry, Vol. 2010, 2010, Article ID: 296215. doi:10.1155/2010/296215

[14]   M. A. Taher, S. E. Jarelnabbi, A. G. M. Al-Sehemi, S. M. El-Medani and R. M. Ramadan, “Synthesis and Spectroscopic Studies of Some New Metal Carbonyl Derivatives of 1-(2-Pyridylazo)-2-naphthol,” Journal of Coordination Chemistry, Vol. 62, No. 8, 2009, pp. 1293-1301. doi:10.1080/00958970802541736

[15]   O. A. M. Ali, L. H. Abdel-Rahman and R. M. Ramadan, “Ruthenium Carbonyl Derivatives of N-salicylidene-2- hydroxyaniline Schiff Base,” Journal of Coordination Chemistry, Vol. 60, 2007, pp. 2335-2342. doi:10.1080/00958970701263952

[16]   S. M. El-Medani, O. A. M. Ali, H. A. Mohamed and R. M. Ramadan, “Spectroscopic, Thermal and X-Ray Crystal Structure Studies of Some Bis-(pyrazine-2-carbo- xylato) Nickel(II) Complexes,” Journal of Coordination Chemistry, Vol. 58, 2005, pp. 1429-1437. doi:10.1080/00958970500156761

[17]   J. Schram, M. Tkadlecová, S. Pataridis, L. Soukupová, V. Blechta, J. Roithová and O. Exner, “Ring-Substituted Benzohydroxamic Acids: 1H, 13C and 15N NMR Spectra and NH-OH Proton Exchange,” Magnetic Resonance in Chemistry, Vol. 43, 2005, pp. 535-542. doi:10.1002/mrc.1586

[18]   P. Bindu, J. V. Kingston and M. N. S. Rao, “Dianionic Silicate Derivatives of Transition Metals: Synthesis by a Facile Ion Exchange Route, Characterization and Thermolysis Studies,” Polyhedron, Vol. 23, No. 4, 2004, pp. 679-686. doi:10.1016/j.poly.2003.11.003

[19]   S. Kannan, A. J. James and P. R. Sharp, “Reaction Chemistry of [Pd2(μ-OH)2L4]2+ with Aryl Amines.: Structures of [Pd2(μ-OH){μ-NH(p-tol)}(PPh3)4](BF4)2, [Pd(η3-CH2C(NH(p-tol)CH2)(PPh3)2](BF4) and [Pd(PMe2Ph)2(μ-PF2O2)]2(PF6)2,” Inorganica Chimica Acta, Vol. 345, 2003, pp. 8-14. doi:10.1016/S0020-1693(02)01278-1

[20]   F. A. Cotton, G. Wilkinson, C. A. Murillo and M. Bochmann, “Advanced Inorganic Chemistry,” 6th Edition, Willey, New York, 1999.

[21]   F. H. Allen, O. Kennard, D. G. Watson, L. Brammer and A. G. Orpen, “Tables of Bond Lengths Determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds,” Journal of the Chemical Society, Perkin Transactions II, Vol. 12, 1987, pp. S1-S19. doi:10.1039/p298700000s1

[22]   J. E. McMurry, “Organic Chemistry,” 6th Edition, Brooks/Cole Pub. Co., Pacific Grove, 2003.

[23]   S. M. El-Medani, T. A. Youssef and R. M. Rama-dan, “Spectroscopic and X-Ray Crystal Structural Characterization of the Charge Transfer Complexes of 2-Amino- benzi-midazole with Some Nitrobenzene Derivatives,” Journal of Molecular Structure, Vol. 644, 2003, pp. 77- 87. doi:10.1016/S0022-2860(02)00474-X

 
 
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