Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
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Data de Publicação: | 2011 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional do INPA |
Texto Completo: | https://repositorio.inpa.gov.br/handle/1/16205 |
Resumo: | The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved. |
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MacEdo, Fernando C.Andrei, César CornélioCampiom, DaniloIshikawa, Noemia Kazue2020-05-31T18:05:42Z2020-05-31T18:05:42Z2011https://repositorio.inpa.gov.br/handle/1/1620510.1016/j.tetlet.2011.01.130The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved.Volume 52, Número 14, Pags. 1612-1614Attribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessAromatic CompoundDimethyl EtherElectrophileHydroquinone DerivativeMethyl GroupAb Initio CalculationAcylationDensity Functional TheoryNuclear Overhauser EffectRing OpeningStereochemistryStereospecificityRegioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindranceinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleTetrahedron Lettersengreponame:Repositório Institucional do INPAinstname:Instituto Nacional de Pesquisas da Amazônia (INPA)instacron:INPAORIGINALartigo-inpa.pdfartigo-inpa.pdfapplication/pdf291353https://repositorio.inpa.gov.br/bitstream/1/16205/1/artigo-inpa.pdfa75cdb593f5ae24bdd4953db285299a9MD511/162052020-05-31 14:10:49.297oai:repositorio:1/16205Repositório de PublicaçõesPUBhttps://repositorio.inpa.gov.br/oai/requestopendoar:2020-05-31T18:10:49Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA)false |
dc.title.en.fl_str_mv |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
title |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
spellingShingle |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance MacEdo, Fernando C. Aromatic Compound Dimethyl Ether Electrophile Hydroquinone Derivative Methyl Group Ab Initio Calculation Acylation Density Functional Theory Nuclear Overhauser Effect Ring Opening Stereochemistry Stereospecificity |
title_short |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
title_full |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
title_fullStr |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
title_full_unstemmed |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
title_sort |
Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance |
author |
MacEdo, Fernando C. |
author_facet |
MacEdo, Fernando C. Andrei, César Cornélio Campiom, Danilo Ishikawa, Noemia Kazue |
author_role |
author |
author2 |
Andrei, César Cornélio Campiom, Danilo Ishikawa, Noemia Kazue |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
MacEdo, Fernando C. Andrei, César Cornélio Campiom, Danilo Ishikawa, Noemia Kazue |
dc.subject.eng.fl_str_mv |
Aromatic Compound Dimethyl Ether Electrophile Hydroquinone Derivative Methyl Group Ab Initio Calculation Acylation Density Functional Theory Nuclear Overhauser Effect Ring Opening Stereochemistry Stereospecificity |
topic |
Aromatic Compound Dimethyl Ether Electrophile Hydroquinone Derivative Methyl Group Ab Initio Calculation Acylation Density Functional Theory Nuclear Overhauser Effect Ring Opening Stereochemistry Stereospecificity |
description |
The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved. |
publishDate |
2011 |
dc.date.issued.fl_str_mv |
2011 |
dc.date.accessioned.fl_str_mv |
2020-05-31T18:05:42Z |
dc.date.available.fl_str_mv |
2020-05-31T18:05:42Z |
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.uri.fl_str_mv |
https://repositorio.inpa.gov.br/handle/1/16205 |
dc.identifier.doi.none.fl_str_mv |
10.1016/j.tetlet.2011.01.130 |
url |
https://repositorio.inpa.gov.br/handle/1/16205 |
identifier_str_mv |
10.1016/j.tetlet.2011.01.130 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.pt_BR.fl_str_mv |
Volume 52, Número 14, Pags. 1612-1614 |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Tetrahedron Letters |
publisher.none.fl_str_mv |
Tetrahedron Letters |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional do INPA instname:Instituto Nacional de Pesquisas da Amazônia (INPA) instacron:INPA |
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Instituto Nacional de Pesquisas da Amazônia (INPA) |
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INPA |
institution |
INPA |
reponame_str |
Repositório Institucional do INPA |
collection |
Repositório Institucional do INPA |
bitstream.url.fl_str_mv |
https://repositorio.inpa.gov.br/bitstream/1/16205/1/artigo-inpa.pdf |
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Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA) |
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1809928865966981120 |