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...
Guardado en:
| Autores principales: | , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0887624X_v36_n15_p2741_Orgueira |
| Aporte de: |
| id |
todo:paper_0887624X_v36_n15_p2741_Orgueira |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_0887624X_v36_n15_p2741_Orgueira2023-10-03T15:40:58Z Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid Orgueira, H.A. Bueno, M. Funes, J.L. Galbis, J.A. Varela, O. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, H.A. Bueno, M. Funes, J.L. Galbis, J.A. Varela, O. 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. |
| format |
JOUR |
| author |
Orgueira, H.A. Bueno, M. Funes, J.L. Galbis, J.A. Varela, O. |
| author_facet |
Orgueira, H.A. Bueno, M. Funes, J.L. Galbis, J.A. Varela, O. |
| author_sort |
Orgueira, H.A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_0887624X_v36_n15_p2741_Orgueira |
| work_keys_str_mv |
AT orgueiraha synthesisandcharacterizationofchiralpolyamidesderivedfromglycineands5amino4methoxypentanoicacid AT buenom synthesisandcharacterizationofchiralpolyamidesderivedfromglycineands5amino4methoxypentanoicacid AT funesjl synthesisandcharacterizationofchiralpolyamidesderivedfromglycineands5amino4methoxypentanoicacid AT galbisja synthesisandcharacterizationofchiralpolyamidesderivedfromglycineands5amino4methoxypentanoicacid AT varelao synthesisandcharacterizationofchiralpolyamidesderivedfromglycineands5amino4methoxypentanoicacid |
| _version_ |
1782025834928799744 |