New Family of Functionalized Monomers Based on Amines: A Novel Synthesis that Exploits the Nucleophilic Substitution Reaction
Lissette Agüero, Luis G. Guerrero-Ramírez, Issa Katime
DOI: 10.4236/msa.2010.13018   PDF   HTML     7,995 Downloads   14,515 Views   Citations


Chemistry modifications are usually performed to introduce specific group that can increase properties and functionality of materials. In this study, we present the synthesis of six new functionalized monomers prepared by nucleophilic substitution reactions. Reaction of aliphatic and aromatic amines with acryloyl chloride at –20ºC, in presence of triethylamine allowed the synthesis of the corresponding amides. Proton nuclear magnetic resonance (1H NMR) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy and ultraviolet- visible (UV-Vis) measurements confirmed the success of the synthesis with a yield over 90%. These compounds emerged as potentially attractive monomers since they can be used to obtain stimuli-sensitive polymeric materials, due to the presence of amide and pyridine groups.

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L. Agüero, L. Guerrero-Ramírez and I. Katime, "New Family of Functionalized Monomers Based on Amines: A Novel Synthesis that Exploits the Nucleophilic Substitution Reaction," Materials Sciences and Applications, Vol. 1 No. 3, 2010, pp. 103-108. doi: 10.4236/msa.2010.13018.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] . L. Pérez, V. Sáez, E. Hernaz, E. Rodríguez and I. Katime, “Synthesis and Characterization of Reactive Copolymeric Microgels,” Polymer International, Vol. 54, No. 6, 2005, pp. 963-971.
[2] L. G. Guerrero-Ramírez, S. M. Nu?o-Donlucas, L. C. Ces- teros and I. Katime, “Smart Copolymeric Nanohydrogels: Synthesis, Characterization snd Properties,” Material Chemistry and Physics, Vol. 112, No. 3, 2008, pp. 1088- 1092.
[3] L. G. Guerrero-Ramírez, S. Nu?o-Donlucas, L. C. Ces- teros and I. Katime, “Novel Functionalized Nanohy- drogels, Synthesis and some Applications,” Journal of Physics Conference Series, Vol. 127, No. 1, 2008, pp. 1-10.
[4] R. Arshady, “Microspheres for Biomedical Applications: Preparation of Reactive and Labeled Microspheres,” Biomaterials, Vol. 14, No. 1, 1993, 5-15.
[5] J. P. Clayden, N. Greeves, S. G. Warren and P. D. Woth-ers, Organic Chemistry, 1st Edition, Publishing Ltd., Ox-ford, 2000.
[6] J. J. Shiers, M. Shipman, J. H. Hayes and A. M. Z. Slawin, “Rare Example of Nucleophilic Substitution at Vinylic Carbon with Inversion: Mechanism of Methyleneaziridine Formation by Sodium Amide Induced Ring Closure Re- visited,” Journal of American Chemical Society, Vol. 126, No. 22, 2004, pp. 6868-6869.
[7] S. Thamizharasi, P. Gnanasundaram and S. Balasu- bramanian, “Synthesis, Characterization and Reactivity Ratios of Copolymers Derived from 4-Nitrophenyl Acry- late and N-Butyl Methacrylate,” Journal of Applied Polymer Science, Vol. 88, No. 7, 2003, pp. 1817-1824.
[8] J. M. J. Frechet and L. J. Nuyens, “Use of Polymers as Pro-tecting Groups in Organic Synthesis. III. Selective Func-tionalization of Polyhydroxy Alcohols,” Canadian Jour-nal of Chemistry, Vol. 54, No. 6, 1976, pp. 926-934.
[9] A. Dasgupta and S. Sivaram, “Polymerization of Mono-mers Bearing Amide Functionalities,” Macromolecules, Vol. 27, No. 1, 1994, pp. 165.
[10] A. P. Krapcho and C. S. Kuell, “Mono-(BOC)-Protected Diamines. Synthesis of Tert-Butyl-N-Alkyl-N-(2-Amino- ethyl) Carbamates and Tert-Butyl-N-[2-(Alkylamino) Ethyl] Carbamates,” Synthetic Communications, Vol. 23, No. 17, 1993, pp. 2443-2449.
[11] L. Pérez, V. Sáez, E. Hernaz and I. Katime, “Novel pH and Temperature Responsive Methacrylamide Microgels,” Macromolecular Chemistry and Physics, Vol. 210, No. 6, 2009, pp. 467-477.
[12] P. H. Toy and K. D. Janda, “Soluble Polymer-Supported Organic Synthesis,” Chemical Research, Vol. 33, No. 8, 2000, pp. 546-554.
[13] D. C. Snyder, “Conversion of Alcohols to Chlorides by TMSCL and DMSO,” Journal of Organic Chemistry, Vol. 60, No. 8, 1995, pp. 2638-2639.
[14] J. March, Advanced Organic Chemistry, 4th Edition, Wiley, New York, 1992.
[15] W. C. Matthew and P. H. Toy, “An Improved and Gen- eral Synthesis of Monomers for Incorporating Trityl Linker Groups into Polystyrene Synthesis Supports,” Tetrahedron, Vol. 60, No. 12, 2004, pp. 2903-2907.
[16] A. Gomtsyan, “Direct Synthesis of β-Aminoketones from Amides via Novel Sequential Nucleophilic Substitu- tion/Michael Reaction,” Organic Letters, Vol. 2, No. 1, 2000, pp. 11-13.
[17] R. A. Rossi and R.H. de Rossi, “Aromatic Substitution by the SRN1 Mechanism,” ACS Monograph Series, American Chemical Society, No. 178, 1983, p. 178.
[18] N. S. Imyanitov, “Electrophilic Bimolecular Substitution as an Alternative to Nucleophilic Monomolecular Substitution in Inorganic and Organic Chemistry,” Journal of General Chemistry, Vol. 60, No. 3, 1990, pp. 417-419.
[19] J. Sudimack and R. Lee, “Targeted Drug Delivery via the Folate Receptor,” Advanced Drug Delivery Reviews, Vol. 41, No. 2, 2000, pp. 147-162.
[20] V. Saéz, L. Pérez, M. T. Herrero, E. Hernaz and I. Katime, “Chemical Functionalization of Poly (Nitrophenyl Acry-late-Co-Methacryl-Amide) Microgels with Pyridines to Provide them Specific PH-Sensitivity,” Polymer, Vol. 47, No. 2, 2006, pp. 818-819.

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