Conformational study of arbutin by quantum chemical calculations and multivariate analysis
Autor(a) principal: | |
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Data de Publicação: | 2010 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/18074 https://doi.org/10.1016/j.molstruc.2010.04.002 |
Resumo: | A conformational study of the molecule of arbutin (4-hydroxyphenyl-β-d-glucopyranoside) has been undertaken. The molecule is composed by a glucopyranoside moiety bound to a phenol ring. It has eight conformationally relevant dihedral angles, five of them related with the orientation of the hydroxyl groups and the remaining three taking part in the skeleton of the molecule. A systematic search on the conformational space of arbutin was performed using molecular orbital methods, followed by the identification of structural similarities between the different conformers, using multivariate analyses. This approach allowed the grouping of conformers according to their structural affinity and the establishment of correlations between their structures and several properties. Intramolecular interactions involving OH groups were also investigated and correlations between spectroscopic, structural and thermodynamic properties established. The developed strategy might be useful to investigate the structure and structure/properties correlations in other conformationally flexible molecules |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Conformational study of arbutin by quantum chemical calculations and multivariate analysisA conformational study of the molecule of arbutin (4-hydroxyphenyl-β-d-glucopyranoside) has been undertaken. The molecule is composed by a glucopyranoside moiety bound to a phenol ring. It has eight conformationally relevant dihedral angles, five of them related with the orientation of the hydroxyl groups and the remaining three taking part in the skeleton of the molecule. A systematic search on the conformational space of arbutin was performed using molecular orbital methods, followed by the identification of structural similarities between the different conformers, using multivariate analyses. This approach allowed the grouping of conformers according to their structural affinity and the establishment of correlations between their structures and several properties. Intramolecular interactions involving OH groups were also investigated and correlations between spectroscopic, structural and thermodynamic properties established. The developed strategy might be useful to investigate the structure and structure/properties correlations in other conformationally flexible moleculesElsevier2010-06info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/18074http://hdl.handle.net/10316/18074https://doi.org/10.1016/j.molstruc.2010.04.002engAraujo-Andrade, CuauhtémocLopes, SusyFausto, RuiGómez-Zavaglia, Andreainfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2021-09-03T10:13:59Zoai:estudogeral.uc.pt:10316/18074Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:47.110867Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
title |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
spellingShingle |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis Araujo-Andrade, Cuauhtémoc |
title_short |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
title_full |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
title_fullStr |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
title_full_unstemmed |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
title_sort |
Conformational study of arbutin by quantum chemical calculations and multivariate analysis |
author |
Araujo-Andrade, Cuauhtémoc |
author_facet |
Araujo-Andrade, Cuauhtémoc Lopes, Susy Fausto, Rui Gómez-Zavaglia, Andrea |
author_role |
author |
author2 |
Lopes, Susy Fausto, Rui Gómez-Zavaglia, Andrea |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Araujo-Andrade, Cuauhtémoc Lopes, Susy Fausto, Rui Gómez-Zavaglia, Andrea |
description |
A conformational study of the molecule of arbutin (4-hydroxyphenyl-β-d-glucopyranoside) has been undertaken. The molecule is composed by a glucopyranoside moiety bound to a phenol ring. It has eight conformationally relevant dihedral angles, five of them related with the orientation of the hydroxyl groups and the remaining three taking part in the skeleton of the molecule. A systematic search on the conformational space of arbutin was performed using molecular orbital methods, followed by the identification of structural similarities between the different conformers, using multivariate analyses. This approach allowed the grouping of conformers according to their structural affinity and the establishment of correlations between their structures and several properties. Intramolecular interactions involving OH groups were also investigated and correlations between spectroscopic, structural and thermodynamic properties established. The developed strategy might be useful to investigate the structure and structure/properties correlations in other conformationally flexible molecules |
publishDate |
2010 |
dc.date.none.fl_str_mv |
2010-06 |
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 |
http://hdl.handle.net/10316/18074 http://hdl.handle.net/10316/18074 https://doi.org/10.1016/j.molstruc.2010.04.002 |
url |
http://hdl.handle.net/10316/18074 https://doi.org/10.1016/j.molstruc.2010.04.002 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
|
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1799133908007124992 |