Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity

1,6-Diaminohexane and a 2-(S)-hydroxypentanedioic acid 5,2-lactone derivative (3) were polycondensed to afford an aregic polyamide 4. A chiral monomer (5) having a 2-fold axis of symmetry was chemoselectively constructed from 3, and upon polymerization with the diamine led to an AABB-type polyamide...

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Autores principales: Orgueira, Hernan Antonio, Erra Balsells, Rosa, Varela, Oscar José
Publicado: 2001
Materias:
Copolymerization
Crystal orientation
Crystal symmetry
Crystalline materials
Homopolymerization
Infrared spectroscopy
Mass spectrometry
Molecular weight
Monomers
Polycondensation
Synthesis (chemical)
Viscosity measurement
Stereoregularity
Syndioregic orientations
Polyamides
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00249297_v34_n4_p687_Orgueira
http://hdl.handle.net/20.500.12110/paper_00249297_v34_n4_p687_Orgueira
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00249297_v34_n4_p687_Orgueira
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spelling paper:paper_00249297_v34_n4_p687_Orgueira2023-06-08T14:52:33Z Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity Orgueira, Hernan Antonio Erra Balsells, Rosa Varela, Oscar José Copolymerization Crystal orientation Crystal symmetry Crystalline materials Homopolymerization Infrared spectroscopy Mass spectrometry Molecular weight Monomers Polycondensation Synthesis (chemical) Viscosity measurement Stereoregularity Syndioregic orientations Polyamides 1,6-Diaminohexane and a 2-(S)-hydroxypentanedioic acid 5,2-lactone derivative (3) were polycondensed to afford an aregic polyamide 4. A chiral monomer (5) having a 2-fold axis of symmetry was chemoselectively constructed from 3, and upon polymerization with the diamine led to an AABB-type polyamide having a syndioregic orientation of the hydroxyl substituents. The analogous isoregic polyamide 11 was also prepared. The three polymers had the same basic structure, but they differ in their regio and stereoregularity. These polyamides, which displayed optical activity, were characterized by IR and 1H and 13C NMR, and their molecular weights were estimated by GPC, viscosimetry, and matrix-assited ultraviolet laser desorption/ionization time-of-flight mass spectrometry (UV-MALDI-TOF MS). This technique was particularly convenient to confirm the repeat units and to detect the functional groups at both ends of the chains. In accordance with their growth processes polyamides 11 and 12 showed the typical UV-MALDI-TOF spectrum for homopolymerization, and polyamides 4 and 6 showed those corresponding to growing by copolymerization. Besides, in agreement with their stereoregularity, polyamides 6 and 11 showed better crystalline properties than those of 4. Fil:Orgueira, H.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. 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. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00249297_v34_n4_p687_Orgueira http://hdl.handle.net/20.500.12110/paper_00249297_v34_n4_p687_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 Copolymerization
Crystal orientation
Crystal symmetry
Crystalline materials
Homopolymerization
Infrared spectroscopy
Mass spectrometry
Molecular weight
Monomers
Polycondensation
Synthesis (chemical)
Viscosity measurement
Stereoregularity
Syndioregic orientations
Polyamides
spellingShingle Copolymerization
Crystal orientation
Crystal symmetry
Crystalline materials
Homopolymerization
Infrared spectroscopy
Mass spectrometry
Molecular weight
Monomers
Polycondensation
Synthesis (chemical)
Viscosity measurement
Stereoregularity
Syndioregic orientations
Polyamides
Orgueira, Hernan Antonio
Erra Balsells, Rosa
Varela, Oscar José
Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
topic_facet Copolymerization
Crystal orientation
Crystal symmetry
Crystalline materials
Homopolymerization
Infrared spectroscopy
Mass spectrometry
Molecular weight
Monomers
Polycondensation
Synthesis (chemical)
Viscosity measurement
Stereoregularity
Syndioregic orientations
Polyamides
description 1,6-Diaminohexane and a 2-(S)-hydroxypentanedioic acid 5,2-lactone derivative (3) were polycondensed to afford an aregic polyamide 4. A chiral monomer (5) having a 2-fold axis of symmetry was chemoselectively constructed from 3, and upon polymerization with the diamine led to an AABB-type polyamide having a syndioregic orientation of the hydroxyl substituents. The analogous isoregic polyamide 11 was also prepared. The three polymers had the same basic structure, but they differ in their regio and stereoregularity. These polyamides, which displayed optical activity, were characterized by IR and 1H and 13C NMR, and their molecular weights were estimated by GPC, viscosimetry, and matrix-assited ultraviolet laser desorption/ionization time-of-flight mass spectrometry (UV-MALDI-TOF MS). This technique was particularly convenient to confirm the repeat units and to detect the functional groups at both ends of the chains. In accordance with their growth processes polyamides 11 and 12 showed the typical UV-MALDI-TOF spectrum for homopolymerization, and polyamides 4 and 6 showed those corresponding to growing by copolymerization. Besides, in agreement with their stereoregularity, polyamides 6 and 11 showed better crystalline properties than those of 4.
author Orgueira, Hernan Antonio
Erra Balsells, Rosa
Varela, Oscar José
author_facet Orgueira, Hernan Antonio
Erra Balsells, Rosa
Varela, Oscar José
author_sort Orgueira, Hernan Antonio
title Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
title_short Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
title_full Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
title_fullStr Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
title_full_unstemmed Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
title_sort synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
publishDate 2001
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00249297_v34_n4_p687_Orgueira
http://hdl.handle.net/20.500.12110/paper_00249297_v34_n4_p687_Orgueira
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AT errabalsellsrosa synthesisofchiralpolyhydroxypolyamideshavingchainsofdefinedregioandstereoregularity
AT varelaoscarjose synthesisofchiralpolyhydroxypolyamideshavingchainsofdefinedregioandstereoregularity
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