Spectroscopic and molecular structure characterization of the bis(2-aminophenol)(5, 10, 15, 20-tetraphenylporphyrinato) cobalt(II) complex

DOI: 10.4236/ojic.2012.24012   PDF   HTML     6,751 Downloads   11,785 Views   Citations

Abstract

The reaction of the cobalt(II) meso-tetraphenylporphyrin (TPP) starting material with an excess of 2-aminophenol (Hon) in organic solvents, yields the cobalt(II) porphyrin species [CoII(TPP)(Hon)2] (1). This compound has been characterized by UV-vis., IR, MSI MS and 1H NMR spectroscopy. The UV-vis data and especially the proton NMR results, for the isolated product, indicated that complex 1 is a Co(II) mesoporphyrin derivative.The X-ray molecular structure of the title compound bis(2-aminophenol) (tetraphenylporphyrinato) cobalt(II) has been determined. This structure is the first one reported of a metalloporphyrin with a 2-aminophenol axial ligand species. The central metal is hexacoordinated by the four nitrogen atoms of the pyrrole rings and the nitrogen atoms of the two Hon trans axial ligands.

Share and Cite:

Belghith, Y. , Mansour, A. , Daran, J. and Nasri, H. (2012) Spectroscopic and molecular structure characterization of the bis(2-aminophenol)(5, 10, 15, 20-tetraphenylporphyrinato) cobalt(II) complex. Open Journal of Inorganic Chemistry, 2, 81-87. doi: 10.4236/ojic.2012.24012.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] Gerber, T.I.A., Luzipo, D. and Mayer, P. (2004) The reaction of the cis-dioxorhenium(V) core with N,O-donor ligands: monoand bidentate coordination of 3-methyl2-aminophenol. Inorganica Chimica Acta , 357, 429-435. HUdoi:10.1016/j.ica.2009.02.037
[2] Hassenein, M., Abdo M., Gerges, S. and El-Khalafy, S. (2008) Study of the oxidation of 2-aminophenol by molecular oxygen catalyzed by cobalt(II) phthalocyaninetetrasodiumsulfonate in water. Journal of Molecular Catalysis A, 287, 53-56. HUdoi:10.1016/j.molcata.2006.11.045UH
[3] Abbreviations used: TPP: dianion of meso-tetraphenylporphyrin; Hon: 2-aminophenol (or ortho-aminophenol); OAc: acetato ; ?2-AT: ?2-3-amino-(S)-tyrosinato; adtpb: (2-amino-4,6-di-t-butylphenol-N); noo’(2,4-di-tbutyl-6) (salicylideneamino) phenolato-N-O-O’; d: opa2aminophenolato-N,O; PhCN: benzonitrile; BAP: tetrabutylammonium perchlorate.
[4] Gao, X.-Y., Xing, L.-X., Chen, Z.-F., Bao, Y.-C., Yang, J.-H., Wu, M.-F., Xiong, R.-G., You, X.-Z. and Fun, H.-K. (2003). Synthesis and crystal structure of a biologically relevant homochiral two-dimensional metal-organic herring-bone molecular grid: Bis(3-amino-(S)-tyrosinato) cobalt(II). Chinese Journal of Inorganic Chemistry, 19, 802.
[5] Alder, A.D., Longo, F.R, Finarelli, J.D., Gildmacher, J., Assour, J. and Korsakoff, L. (1967) A simplified synthesis for mesotetraphenyl porphine. Journal of Organic Chemistry, 32, 476-476. HUdoi:10.1021/jo01288a053UH
[6] Mansour, A., Belkhiria , M.S., Daran, J.C. and Nasri, H. (2010) (5,10,15,20-tetraphenylporphyrinato) cobalt(II)18-crown-6 (1/1). Acta Crystallographica Section E, 66, m509-m510. HUdoi:10.1107/S1600536810012080U
[7] Oxford Diffraction (2009). Chrysalis Promotions, Oxford Diffraction Ltd., Abingdon, Oxfordshire, England. HUdoi:10.1021/ic50166a056U
[8] Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G.L., De Caro, L., Giacovazzo, C., Polidori, G. and Spagna ,R. (2005) SIR2004: An improved tool for crystal structure determination and refinement. Journal of Applied Crystallography, 38, 381-388. HUdoi:10.1107/S002188980403225XU
[9] Sheldrick, G.M. (2008) A short history of SHELX. Acta Crystallographica Section E, 64, 112-122. HUdoi.10.1107/S0108767307043930U
[10] Mansour, A. and Nasri, H. (2012) “Synthesis, crystal structure and spectroscopic characterization of 1D Co(II) coordination polymers {[CoII(α,β,α,β-TpivPP)(μ-4,4’-bp y)2]}n and {[CoII(TPP)(μ-4,4’-bpy)2]}n with the (a,b,a,btetrakis(o-pivalamidophenyl)porphyrin) a,b,a,b-TpivPP) and the tetraphenylporphyrin (TPP). In press.
[11] Hoshino, M., Sonoki, H., Miyazaki,Y., Iimura, Y. and Yamamoto, K. (2000) Structure and photo chemistry of dicyanocobalt(III) tetraphenyl porphyrin. Photochromic reaction caused by photodissociation of axial ligand. Inorganic Chem istry, 39, 4850-4857. HUdoi: 10.1021/ic000408xUH
[12] Shirazi, A. and Goff, H.M. (1982) Carbon-13 and proton NMR spectroscopy of fourand five-coordinate cobalt(II) porphyrins: Analysis of NMR isotropic shifts. Inorganic Chemistry, 21, 3420-3425. HUdoi: 10.1021/ic00139a030U
[13] La Mar, G. N. and Walker, F.A. (1973) Proton nuclear magnetic resonance and electron spin resonance investigation of axial solvation in planar, low-spin cobalt(II) porphyrin complexes. Journal of American Chemical Society, 95, 1790-1796. HUdoi:10.1021/ja00787a017U
[14] Choi I-K., Lin, Y., Wei, Z. and Rayan, M.D. (1997) Reactions of hydroxylamine with metal porphyrins. Inorganic Chemistry, 36, 3113-3118. HUdoi:10.1021/ic9605783UH
[15] Farrugia, L.J. (1997) ORTEP-3 for windows a ver sion of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography, 30, 565. HUdoi:10.1107/S0021889897003117U
[16] Allen, F.H. (2002) The Cambridge Structural Data base: A quarter of a million crystal structures and rising. Acta Crystallographica Section B, 58, 380-388. HUdoi:10.1107/S0108768102003890U
[17] Mayer, P., Potgieter, K.C. and Gerber, T.I.A. (2010) Rhenium (I), (III) and (V) complexes of tridentate ONX (X=O, N, S)-donor Schiff bases. Polyhedron, 29, 14231430. HUdoi: 10.1016/j.poly.2010.01.013UH
[18] Gerber, T.I.A., Betz, R., Booysen, I.N., Potgieter, K.C. and Mayer, P. (2011) Coordination of bidentate aniline derivatives to the fac-[Re(CO)3]+ core. Polyhedron, 30, 1739-1745. HUdoi: 10.1016/j.poly.2011.04.019UH
[19] Iimura,Y., Sakurai, T. and Yamamoto, K. ( 1988) The crystal and molecular structure of aquachloro (meso-tetraphenylporphyrinato) cobalt(III). Bulletin of the Chemical Society of Japan, 61, 821-826. HUdoi: 10.1246/bcsj.61.821UH.

  
comments powered by Disqus

Copyright © 2020 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.