Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid

Stereoregular, enantiomerically pure, chiral polyamides of the -AB- type, containing a natural (glycine) and a synthetic [(S)-5-amino-4-methoxypentanoic acid (AMP)] component have been prepared by the active ester polycondensation method. Thus, polyamide 7 was obtained by polycondensation of the con...

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Autores principales: Orgueira, Hernan Antonio, Varela, Oscar José
Publicado: 1998
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Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0887624X_v36_n15_p2741_Orgueira
http://hdl.handle.net/20.500.12110/paper_0887624X_v36_n15_p2741_Orgueira
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spelling paper:paper_0887624X_v36_n15_p2741_Orgueira2023-06-08T15:46:52Z Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid Orgueira, Hernan Antonio Varela, Oscar José Chiral polyamides Glycine Stereoregular polymers ω-amino acids Amino acids Crystal microstructure Crystalline materials Esters Evaporation Infrared spectroscopy Molecular structure Nuclear magnetic resonance spectroscopy Plastic films Polycondensation Synthesis (chemical) Aminomethoxypentanoic acid Elemental analysis Formic acid Glycine Pentachlorophenyl ester Polyamides Stereoregular, enantiomerically pure, chiral polyamides of the -AB- type, containing a natural (glycine) and a synthetic [(S)-5-amino-4-methoxypentanoic acid (AMP)] component have been prepared by the active ester polycondensation method. Thus, polyamide 7 was obtained by polycondensation of the conveniently activated H2NGly-AMPCO2R unit (6). In this reaction, 7 appeared accompanied by a considerable amount of cyclic (Gly-AMP)2 (8), which makes the isolation and purification of 7 difficult. The formation of cyclic byproducts could be avoided by preparing and polymerizing the oligoamide H2NGly-AMP-AMPCO2R (11), which has the terminal carboxyl group activated as the pentachlorophenyl ester. The resulting polyamide (12) was obtained in 85% yield and free of macrolactams, such as 8. The new polyamides 7 and 12 were characterized by elemental analysis and infrared and 1H- and 13C-nuclear magnetic resonance spectroscopies. Thermal studies revealed that 12 is crystalline and yields films with spherulitic texture by slow evaporation of formic acid solutions. © 1998 John Wiley & Sons, Inc. Fil:Orgueira, H.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1998 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0887624X_v36_n15_p2741_Orgueira http://hdl.handle.net/20.500.12110/paper_0887624X_v36_n15_p2741_Orgueira
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Chiral polyamides
Glycine
Stereoregular polymers
ω-amino acids
Amino acids
Crystal microstructure
Crystalline materials
Esters
Evaporation
Infrared spectroscopy
Molecular structure
Nuclear magnetic resonance spectroscopy
Plastic films
Polycondensation
Synthesis (chemical)
Aminomethoxypentanoic acid
Elemental analysis
Formic acid
Glycine
Pentachlorophenyl ester
Polyamides
spellingShingle Chiral polyamides
Glycine
Stereoregular polymers
ω-amino acids
Amino acids
Crystal microstructure
Crystalline materials
Esters
Evaporation
Infrared spectroscopy
Molecular structure
Nuclear magnetic resonance spectroscopy
Plastic films
Polycondensation
Synthesis (chemical)
Aminomethoxypentanoic acid
Elemental analysis
Formic acid
Glycine
Pentachlorophenyl ester
Polyamides
Orgueira, Hernan Antonio
Varela, Oscar José
Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
topic_facet Chiral polyamides
Glycine
Stereoregular polymers
ω-amino acids
Amino acids
Crystal microstructure
Crystalline materials
Esters
Evaporation
Infrared spectroscopy
Molecular structure
Nuclear magnetic resonance spectroscopy
Plastic films
Polycondensation
Synthesis (chemical)
Aminomethoxypentanoic acid
Elemental analysis
Formic acid
Glycine
Pentachlorophenyl ester
Polyamides
description Stereoregular, enantiomerically pure, chiral polyamides of the -AB- type, containing a natural (glycine) and a synthetic [(S)-5-amino-4-methoxypentanoic acid (AMP)] component have been prepared by the active ester polycondensation method. Thus, polyamide 7 was obtained by polycondensation of the conveniently activated H2NGly-AMPCO2R unit (6). In this reaction, 7 appeared accompanied by a considerable amount of cyclic (Gly-AMP)2 (8), which makes the isolation and purification of 7 difficult. The formation of cyclic byproducts could be avoided by preparing and polymerizing the oligoamide H2NGly-AMP-AMPCO2R (11), which has the terminal carboxyl group activated as the pentachlorophenyl ester. The resulting polyamide (12) was obtained in 85% yield and free of macrolactams, such as 8. The new polyamides 7 and 12 were characterized by elemental analysis and infrared and 1H- and 13C-nuclear magnetic resonance spectroscopies. Thermal studies revealed that 12 is crystalline and yields films with spherulitic texture by slow evaporation of formic acid solutions. © 1998 John Wiley & Sons, Inc.
author Orgueira, Hernan Antonio
Varela, Oscar José
author_facet Orgueira, Hernan Antonio
Varela, Oscar José
author_sort Orgueira, Hernan Antonio
title Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
title_short Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
title_full Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
title_fullStr Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
title_full_unstemmed Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
title_sort synthesis and characterization of chiral polyamides derived from glycine and (s)-5-amino-4-methoxypentanoic acid
publishDate 1998
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0887624X_v36_n15_p2741_Orgueira
http://hdl.handle.net/20.500.12110/paper_0887624X_v36_n15_p2741_Orgueira
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