AJAC  Vol.5 No.16 , November 2014
Branched Polyamines Functionalized with Proposed Reaction Pathways Based on 1H-NMR, Atomic Absorption and IR Spectroscopies
Abstract: Three novel branched polyamines N,N,N’,N’-tetrakis-[3((pyridine-2-methyl)-amine) propyl]-1,4- butanediamine (1), N,N,N’,N’-tetrakis-[N-((2-methylpyridine)ethyl)propanamide]ethylenediamine (2) and N,N,N’,N’-tetrakis-[3((2-hidroxibenziliden)-amine)propyl]-1,4-butanediamine (3), were synthesized starting from 2-pyridinecarboxaldeyde with DAB-Am-4 for 1, PAMAM G0 for 2 and from salicylaldehyde with DAB-Am-4 for 3. The pathway reactions have been proposed by 1H-NMR, IR and Atomic Absorption Spectroscopy. The optimal reaction time was set by IR spectroscopy following aldehyde  peak modification. 1 and 2 were obtained as both hydrochlorides and as free amines and 3 only as free imine. These polyamines were characterized by UV-Vis, IR, 1H-NMR and 13C-NMR and Mass Spectrometry.
Cite this paper: Cervantes-Mejía, V. , Baca-Solis, E. , Caballero-Jiménez, J. , Merino-García, R. , Cruz-Gatica, J. , Moreno-Martínez, G. and Reyes-Ortega, Y. (2014) Branched Polyamines Functionalized with Proposed Reaction Pathways Based on 1H-NMR, Atomic Absorption and IR Spectroscopies. American Journal of Analytical Chemistry, 5, 1090-1101. doi: 10.4236/ajac.2014.516116.

[1]   Vogtle, F., Buhleier, E.W. and Wehner, W. (1978) Cascade and Nonskid-Chain-Like Syntheses of Molecular Cavity Topologies. Synthesis, 2, 155-158.

[2]   Bosman, A.W., Janssen, H.M. and Meijer, E.W. (1999) About Dendrimers: Structure, Physical Properties, and Applications. Chemical Reviews, 99, 1665-1688.

[3]   Lee, B., Park, Y.H., Hwang, Y.T., Oh, W., Yoon, J. and Ree, M. (2005) Ultralow-k Nanoporous Organosilicate Dielectric Films Imprinted with Dendritic Spheres. Nature Materials, 4, 147-150.

[4]   Amama, P.B., Maschmann, M.R., Fisher, T.S. and Sands, T.D. (2006) Dendrimer-Templated Fe Nanoparcles for the Growth of Single-Wall Carbon Nanotubes by Plasma-Enhanced CVD. Journal of Physical Chemistry B, 110, 10636-10644.

[5]   Twyman, L.J., King, A.S.H. and Martin, I.K. (2002) Catalysis inside Dendrimers. Chemical Society Reviews, 31, 69-82.

[6]   Kainz, Q.M. and Reiser, O. (2014) Polymer and Dendrimer-Coated Magnetic Nanoparticles as Versatile Supports for Catalyst, Scavengers, and Reagents. Accounts of Chemical Research, 47, 667-667.

[7]   Mynar, J.L., Lowery, T.J., Wemmer, D.E., Pines, A. and Fréchet, J.M. (2006) Single Quantum Dot-Micelles Coated with Silica Shell as Potentially Non-Cytotoxic Fluorescent Cell Tracers. Journal of the American Chemical Society, 128, 6334-6335.

[8]   Lo, S.-Ch. and Burn, P.L. (2007) Development of Dendrimers: Macromolecules for Use in Organic Light-Emmitting Diodes and Solar Cells. Chemical Reviews, 107, 1097-1116.

[9]   Zhang, M., Guo, R., Kéri, M., Bányai, I., Zheng, Y., Cao, M. and Shi, X. (2014) Impact of Dendrimer Surface Functional Groups on the Release of Doxorubicin from Dendrimer Carriers. Journal of Physical Chemistry B, 118, 1696-1706.

[10]   Li, X., Haba, Y., Ochi, K., Yuba, E., Harada, A. and Kono, K. (2013) PAMAM Dendrimers with Oxyethylene Unit-Enriched Surface as Biocompatible Temperature-Sensitive Dendrimers. Bioconjugate Chemistry, 24, 282-290.

[11]   Fulton, D.A., Elemento, E.M., Aime, S., Chaabane, L., Botta, M. and Parker, D. (2006) Glycoconjugates of Gadolinium Complexes for MRI Applications. Chemical Communications, 10, 1064-1066.

[12]   Schick, I., Lorenz, S., Gehrig, D., Schilmann, A.M., Baur, H., Panthofer, M., Fischer, K., Starnd, D., Laquai, F. and Tremel, W. (2014) Multifunctional Two-Photon Active Silica-Coated AuMnO Janus Particles for Selective Dual Functionalization and Imaging. Journal of the American Chemical Society, 136, 2473-2483.

[13]   Lee, C.C., MacKay, J.A., Fréchet, J.M.J. and Szoka, F.C. (2005) Designing Dendrimers for Biological Applications. Nature Biotechnology, 23, 1517-1526.

[14]   Bazzicalupi, C., Bianchi, A., Giorgi, C., Gratteri, P., Mariani, P. and Valtancoli, B. (2013) Metal Ion Binding by a G-2 Poly(Ethylene Imine) Dendrimer. Ion-Directed Self-Assembling of Hierarchical Mono- and Two-Dimensional Nanostructured Materials. Inorganic Chemistry, 52, 2125-2137.

[15]   Bergeron, R.J. (1986) Methods for the Selective Modification of Spermidine and Its Homologues. Accounts of Chemical Research, 19, 105-113.

[16]   Kuksa, V., Buchnan, R. and Lin, P.T. (2000) Synthesis of Polyamines, Their Derivatives, Analogues and Conjugates. Synthesis, 2000, 1189-1207.

[17]   Sánchez-Sandoval, A., Alvarez-Toledano, C., Gutierrez-Pérez, R. and Reyes-Ortega, Y. (2003) A Modified Procedure for the Preparation of Linear Polyamines. Synthetic Communications, 33, 481-492.

[18]   McMurry, J. (2001) Química Orgánica. 5th Edition, Thomson International, México.

[19]   Atkins, P.W., Overton, T.L., Rourke, J.P., Weller, M.T. and Armstrong, F.A. (2010) Inorganic Chemistry. Oxford University Press, New York.

[20]   Tanaka, K. and Toda, F. (2000) Solvent-Free Organic Synthesis. Chemical Reviews, 100, 1025-1074.

[21]   Nakamoto, K. (1999) Infrared and Raman Spectra of Inorganic and Coordination Compounds. John Wiley and Sons, New York.

[22]   Cimerman, Z., Galic, N. and Bosner, B. (1997) The Schiff Bases of Salicylaldehyde and Aminopyridines as Highly Sensitive Analytical Reagents. Analytica Chimica Acta, 343, 145-153.

[23]   Smith, G.S. (2003) An Investigation into the Synthesis, Characterization and Some Applications of Novel-Containing Polymers and Dendrimers of Transition Metals. Doctoral Thesis.

[24]   Louie, O., Massoudi, A., Vahedi, H., Asadi, H. and Sajjadifar, S. (2012) The Modification of Poly Amidoamine (PAMAM-G0.5) by Cytosine. Engineering, 5, 103-105.

[25]   Radhi, M.M. and Mel-Bermani, M.F. (1990) Infrared Studies of the Conformation in Salicylaldehyde, Methylsalicylate and Ethylsalicylate. Spectrochimica Acta Part A, 46, 33-42.

[26]   Yildiz, M., Kilic, Z. and Hokelek, T. (1998) Intramolecular Hydrogen Bonding and Tautomerism in Schiff Bases. Part 1. Structure of 1,8-Dif[N-2-Oxy-Phenyl-Salicylidene]-3,6-Dioxaoctane. Journal of Molecular Structure, 441, 1-10.

[27]   Freedman, H.H. (1961) Intramolecular H-Bonds. I. Spectroscopic Study of the Hydrogen Bond between Hydroxyl and Nitrogen. Journal of the American Chemical Society, 83, 2900-2905.

[28]   Colthup, N.B., Daly, L.H. and Wiberley, S.E. (1990) Introduction to Infrared and Raman Spectroscopy. 3rd Edition, Academic Press, Waltham.

[29]   Nazir, H., Yildiz, M., Yilmaz, H., Tahir, M.N. and ülkü, D. (2000) Intramolecular Hydrogen Bonding and Tautomerism in Schiff Bases. Structure of N-(2-Pyridil)-2-Oxo-1-Naphthylidenemethylamine. Journal of Molecular Structure, 524, 241-250.

[30]   Pavia, D.L., Lampman, G.M. and Kriz, G.S. (1996) Introduction to Spectroscopy. Saunders Golden-Sunburst Series, USA.

[31]   Drago, R.S. (1992) Physical Methods in Chemistry. 2nd Edition, Saunders College Publishing, USA.

[32]   Pretsch, E., Bühlmann, P. and Affolter, C. (2000) Structure Determination of Organic Compounds. Springer, London.