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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid
Autor:Orgueira, H.A.; Bueno, M.; Funes, J.L.; Galbis, J.A.; Varela, O.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Pabellon 2-Ciudad Universitaria, 1428 Buenos Aires, Argentina
Depto. de Quim. Organ. y Farmaceut., Facultad de Farmacia, Universidad de Sevilla, 41071-Seville, Spain
Palabras clave: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
Año:1998
Volumen:36
Número:15
Página de inicio:2741
Página de fin:2748
DOI: http://dx.doi.org/10.1002/(SICI)1099-0518(19981115)36:15<2741::AID-POLA10>3.0.CO;2-E
Título revista:Journal of Polymer Science, Part A: Polymer Chemistry
Título revista abreviado:J Polym Sci Part A
ISSN:0887624X
CODEN:JPACE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0887624X_v36_n15_p2741_Orgueira

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Citas:

---------- APA ----------
Orgueira, H.A., Bueno, M., Funes, J.L., Galbis, J.A. & Varela, O. (1998) . Synthesis and characterization of chiral polyamides derived from glycine and (S)-5-amino-4-methoxypentanoic acid. Journal of Polymer Science, Part A: Polymer Chemistry, 36(15), 2741-2748.
http://dx.doi.org/10.1002/(SICI)1099-0518(19981115)36:15<2741::AID-POLA10>3.0.CO;2-E
---------- CHICAGO ----------
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" . Journal of Polymer Science, Part A: Polymer Chemistry 36, no. 15 (1998) : 2741-2748.
http://dx.doi.org/10.1002/(SICI)1099-0518(19981115)36:15<2741::AID-POLA10>3.0.CO;2-E
---------- MLA ----------
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" . Journal of Polymer Science, Part A: Polymer Chemistry, vol. 36, no. 15, 1998, pp. 2741-2748.
http://dx.doi.org/10.1002/(SICI)1099-0518(19981115)36:15<2741::AID-POLA10>3.0.CO;2-E
---------- VANCOUVER ----------
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. J Polym Sci Part A. 1998;36(15):2741-2748.
http://dx.doi.org/10.1002/(SICI)1099-0518(19981115)36:15<2741::AID-POLA10>3.0.CO;2-E