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Synthesis and polymerization of chiral acrylamidosulfonic acids

Journal Article


Abstract


  • Reductive amination of (1S)-(+)-10-camphorsulfonic acid with NaCNBH3/NH4OAc has afforded diastereomeric exo- and endo-aminosulfonic acids, that can be separated by crystallization from methanol. Treatment of these diastereomers with acryloyl chloride gave high yields of novel, chiral acrylamides that incorporate both a sulfonic acid substituent and a chiral auxiliary. The free radical (AIBN) polymerization of these acrylamides gave high yields (84-90%) of novel, water-soluble polyacrylamides (Mw = 5500-7800). 1H NMR studies showed these to be essentially atactic. Their circular dichroism spectra were similar to their corresponding acrylamide monomers. This indicates that the sulfonic acid chiral auxiliary in the monomer precursors does not induce and/or maintain macroasymmetry in the resulting polyacrylamide chains. Hydrogels with equilibrium water contents as high as 99.96% could be obtained by copolymerizing {(NH4)2S2O8 initiator} these chiral acrylamides with equimolar acrylamide and varying ratios of N,N′-methylenebisacrylamide as cross-linker.

Publication Date


  • 1998

Citation


  • Ashraf, S. A., Kane-Maguire, L. A. P., Pyne, S. G., & Wallace, G. G. (1998). Synthesis and polymerization of chiral acrylamidosulfonic acids. Macromolecules, 31(25), 8737-8743. doi:10.1021/ma971242v

Scopus Eid


  • 2-s2.0-0346976001

Start Page


  • 8737

End Page


  • 8743

Volume


  • 31

Issue


  • 25

Abstract


  • Reductive amination of (1S)-(+)-10-camphorsulfonic acid with NaCNBH3/NH4OAc has afforded diastereomeric exo- and endo-aminosulfonic acids, that can be separated by crystallization from methanol. Treatment of these diastereomers with acryloyl chloride gave high yields of novel, chiral acrylamides that incorporate both a sulfonic acid substituent and a chiral auxiliary. The free radical (AIBN) polymerization of these acrylamides gave high yields (84-90%) of novel, water-soluble polyacrylamides (Mw = 5500-7800). 1H NMR studies showed these to be essentially atactic. Their circular dichroism spectra were similar to their corresponding acrylamide monomers. This indicates that the sulfonic acid chiral auxiliary in the monomer precursors does not induce and/or maintain macroasymmetry in the resulting polyacrylamide chains. Hydrogels with equilibrium water contents as high as 99.96% could be obtained by copolymerizing {(NH4)2S2O8 initiator} these chiral acrylamides with equimolar acrylamide and varying ratios of N,N′-methylenebisacrylamide as cross-linker.

Publication Date


  • 1998

Citation


  • Ashraf, S. A., Kane-Maguire, L. A. P., Pyne, S. G., & Wallace, G. G. (1998). Synthesis and polymerization of chiral acrylamidosulfonic acids. Macromolecules, 31(25), 8737-8743. doi:10.1021/ma971242v

Scopus Eid


  • 2-s2.0-0346976001

Start Page


  • 8737

End Page


  • 8743

Volume


  • 31

Issue


  • 25