Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations.
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/2031 |
Resumo: | Very few investigations concerning the crystal structure and chemical properties of dioxamic acids have been related in the literature. This work describes the chemical properties of ortho-phenylenebis(oxamic acid) (2) and its new derivative, hydrogeno ortho-phenylenebis(oxamato) benzimidazolium (3) using experimental (FT-IR, NMR, and X-ray single crystal diffraction) and theoretical (HF/3-21G_ and B3LYP/ 6-31G_ calculations) methodologies. Compound 2 displays intramolecular hydrogen bonding between the hydrogen of an amide group and the oxygen atom of another amide group present in the structure. Compound 3 was prepared by a newly developed synthetic route involving decomposition of the dioxamic acid in solution without the presence of metallic ions. Thermodynamic calculations indicate a process via two successive hydrolyzes of the amide groups of 2, followed by condensation with formic acid and finally dehydration. The structure of 3 was solved by X-ray single-crystal diffraction and it consists of meso-helical chains stabilized by intra and intermolecular hydrogen bonds and p–p stacking interactions. |
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Souza, Gilmar Pereira deKonzen, CibeleSimões, Tatiana Renata GomesRodrigues, Bernardo LagesAlcântara, Antônio Flávio de CarvalhoStumpf, Humberto Osório2012-12-14T19:11:45Z2012-12-14T19:11:45Z2012SOUZA, G. P. et al. Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. Journal of Molecular Structure, v. 1016, p. 13–21, 2012. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0022286012000749>. Acesso em: 11 dez. 2012.00222860http://www.repositorio.ufop.br/handle/123456789/2031Very few investigations concerning the crystal structure and chemical properties of dioxamic acids have been related in the literature. This work describes the chemical properties of ortho-phenylenebis(oxamic acid) (2) and its new derivative, hydrogeno ortho-phenylenebis(oxamato) benzimidazolium (3) using experimental (FT-IR, NMR, and X-ray single crystal diffraction) and theoretical (HF/3-21G_ and B3LYP/ 6-31G_ calculations) methodologies. Compound 2 displays intramolecular hydrogen bonding between the hydrogen of an amide group and the oxygen atom of another amide group present in the structure. Compound 3 was prepared by a newly developed synthetic route involving decomposition of the dioxamic acid in solution without the presence of metallic ions. Thermodynamic calculations indicate a process via two successive hydrolyzes of the amide groups of 2, followed by condensation with formic acid and finally dehydration. The structure of 3 was solved by X-ray single-crystal diffraction and it consists of meso-helical chains stabilized by intra and intermolecular hydrogen bonds and p–p stacking interactions.Molecule-based magnetDioxamic acidsSupramolecular chemistryX-ray crystal structureStructural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleO periódico Journal of Molecular Structure concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 3313101198477.info:eu-repo/semantics/openAccessengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://www.repositorio.ufop.br/bitstream/123456789/2031/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINALARTIGO_StructuralCharacterizationDioxamicAcid.pdfARTIGO_StructuralCharacterizationDioxamicAcid.pdfapplication/pdf647550http://www.repositorio.ufop.br/bitstream/123456789/2031/1/ARTIGO_StructuralCharacterizationDioxamicAcid.pdf2868b1ce8d68513dac66e235469108daMD51123456789/20312019-03-15 14:40:46.418oai:localhost: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Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-03-15T18:40:46Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
title |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
spellingShingle |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. Souza, Gilmar Pereira de Molecule-based magnet Dioxamic acids Supramolecular chemistry X-ray crystal structure |
title_short |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
title_full |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
title_fullStr |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
title_full_unstemmed |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
title_sort |
Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. |
author |
Souza, Gilmar Pereira de |
author_facet |
Souza, Gilmar Pereira de Konzen, Cibele Simões, Tatiana Renata Gomes Rodrigues, Bernardo Lages Alcântara, Antônio Flávio de Carvalho Stumpf, Humberto Osório |
author_role |
author |
author2 |
Konzen, Cibele Simões, Tatiana Renata Gomes Rodrigues, Bernardo Lages Alcântara, Antônio Flávio de Carvalho Stumpf, Humberto Osório |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Souza, Gilmar Pereira de Konzen, Cibele Simões, Tatiana Renata Gomes Rodrigues, Bernardo Lages Alcântara, Antônio Flávio de Carvalho Stumpf, Humberto Osório |
dc.subject.por.fl_str_mv |
Molecule-based magnet Dioxamic acids Supramolecular chemistry X-ray crystal structure |
topic |
Molecule-based magnet Dioxamic acids Supramolecular chemistry X-ray crystal structure |
description |
Very few investigations concerning the crystal structure and chemical properties of dioxamic acids have been related in the literature. This work describes the chemical properties of ortho-phenylenebis(oxamic acid) (2) and its new derivative, hydrogeno ortho-phenylenebis(oxamato) benzimidazolium (3) using experimental (FT-IR, NMR, and X-ray single crystal diffraction) and theoretical (HF/3-21G_ and B3LYP/ 6-31G_ calculations) methodologies. Compound 2 displays intramolecular hydrogen bonding between the hydrogen of an amide group and the oxygen atom of another amide group present in the structure. Compound 3 was prepared by a newly developed synthetic route involving decomposition of the dioxamic acid in solution without the presence of metallic ions. Thermodynamic calculations indicate a process via two successive hydrolyzes of the amide groups of 2, followed by condensation with formic acid and finally dehydration. The structure of 3 was solved by X-ray single-crystal diffraction and it consists of meso-helical chains stabilized by intra and intermolecular hydrogen bonds and p–p stacking interactions. |
publishDate |
2012 |
dc.date.accessioned.fl_str_mv |
2012-12-14T19:11:45Z |
dc.date.available.fl_str_mv |
2012-12-14T19:11:45Z |
dc.date.issued.fl_str_mv |
2012 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SOUZA, G. P. et al. Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. Journal of Molecular Structure, v. 1016, p. 13–21, 2012. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0022286012000749>. Acesso em: 11 dez. 2012. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/2031 |
dc.identifier.issn.none.fl_str_mv |
00222860 |
identifier_str_mv |
SOUZA, G. P. et al. Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. Journal of Molecular Structure, v. 1016, p. 13–21, 2012. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0022286012000749>. Acesso em: 11 dez. 2012. 00222860 |
url |
http://www.repositorio.ufop.br/handle/123456789/2031 |
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eng |
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