Does intramolecular hydrogen bond play a key role in the stereochemistry of α- and β-d-glucose?

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorSilla, Josué M.-
Autor(es): dc.creatorCormanich, Rodrigo A.-
Autor(es): dc.creatorRittner, Roberto-
Autor(es): dc.creatorFreitas, Matheus P.-
Data de aceite: dc.date.accessioned2026-02-09T11:52:30Z-
Data de disponibilização: dc.date.available2026-02-09T11:52:30Z-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2020-07-12-
Data de envio: dc.date.issued2014-09-19-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/41846-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/abs/pii/S0008621514002511-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1149364-
Descrição: dc.descriptionFour α- and three β-isomers of the d-glucose were optimized in gas phase using ab initio (MP2) and DFT (ωB97X-D) methods, both using the aug-cc-pVDZ basis set. While earlier works suggest that the orientation of the hydroxyl groups is due to intramolecular hydrogen bonds (H-bonds), the present study reveals that most H-bonds forming five-membered rings are either weak or even do not exist. The quantum theory of atoms in molecules (QTAIM) analysis showed only a few cases of H-bond in d-glucose, particularly for those H-bonds forming six-membered rings, while the non-covalent interactions (NCI) analysis indicated that most intramolecular H-bonds are not strong enough to justify the counter-clockwise arrangement of the OH⋯O chains. Natural bond orbital analysis supported the findings obtained from QTAIM and NCI analyses and indicated that the anomeric effect for d-glucose in the gas phase is governed by a balance of steric, electrostatic, and hyperconjugative interactions.-
Idioma: dc.languageen-
Publicador: dc.publisherElsevier-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceCarbohydrate Research-
Palavras-chave: dc.subjectd-Glucose-
Palavras-chave: dc.subjectHydrogen bond-
Palavras-chave: dc.subjectNBO-
Palavras-chave: dc.subjectNCI-
Palavras-chave: dc.subjectQTAIM-
Palavras-chave: dc.subjectNatural bond orbital (NBO)-
Palavras-chave: dc.subjectNon-covalent interaction (NCI)-
Palavras-chave: dc.subjectQuantum theory of atoms in molecules (QTAIM)-
Título: dc.titleDoes intramolecular hydrogen bond play a key role in the stereochemistry of α- and β-d-glucose?-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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