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dc.contributor.author
Crespi, Ayelen Florencia
dc.contributor.author
Vega, Daniel Roberto
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Sanchez, Veronica Muriel
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Rodríguez Castellón, Enrique
dc.contributor.author
Lazaro Martinez, Juan Manuel
dc.date.available
2024-03-21T12:38:32Z
dc.date.issued
2022-09
dc.identifier.citation
Crespi, Ayelen Florencia; Vega, Daniel Roberto; Sanchez, Veronica Muriel; Rodríguez Castellón, Enrique; Lazaro Martinez, Juan Manuel; Shared Hydrogen Atom Location and Chemical Composition in Picolinic Acid and Pyridoxal Hydrochloride Derivatives Determined by X-ray Crystallography; American Chemical Society; Journal of Organic Chemistry; 87; 20; 9-2022; 13427-13438
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/231121
dc.description.abstract
Three new single-crystal structures were isolated for picolinic acid (2), the trifluoroacetate salt of picolinic acid (1), andpyridoxal hydrochloride (3). These compounds displayed unconventional crystallographic features that must be consideredwhen structural refinements are carried out. Thus, the generated Fourier differences map obtained with the diffraction datacollected at 100 K was crucial to visualize electron densities, which were balanced by either one hydrogen atom or a hydrogen atom with an occupancy factor of 1/2 located between either two carboxylate moieties, two phenolic oxygen atoms, or two pyridinic nitrogen atoms. Moreover, NMR studies were conducted to analyze the bulk chemical composition of single crystals of 2-pyridinecarboxylic acid obtained from the gem-diol/hemiacetal forms and the polymerization products after the treatment of 2-pyridinecarboxaldehyde with TFA:H2O (1) or a diluted Cu(NO3)2 solution (2). The quantitative yield of the pyridoxal hydrochloride crystalline material (3) obtained from a diluted CuCl2 solution was exhaustively characterized by solid-state NMR methods. These methods allowed the resolution of the signals corresponding to the protons of the hydroxyl moiety of the intramolecular hemiacetal group and the phenolic hydrogen. Theoretical calculations using DFT methods were done to complement the atomic location of the hydrogen atoms obtained from the X-ray analysis.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
X-RAY CRYSTALLOGRAPHY
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NUCLEAR MAGNETIC RESONANCE
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DFT
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Shared Hydrogen Atom Location and Chemical Composition in Picolinic Acid and Pyridoxal Hydrochloride Derivatives Determined by X-ray Crystallography
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2023-07-07T22:54:36Z
dc.journal.volume
87
dc.journal.number
20
dc.journal.pagination
13427-13438
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington
dc.description.fil
Fil: Crespi, Ayelen Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
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Fil: Vega, Daniel Roberto. Comisión Nacional de Energía Atómica; Argentina
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Fil: Sanchez, Veronica Muriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
dc.description.fil
Fil: Rodríguez Castellón, Enrique. Universidad de Málaga; España
dc.description.fil
Fil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
dc.journal.title
Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.2c00724
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1021/acs.joc.2c00724
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