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metadata.artigo.dc.title: Does intramolecular hydrogen bond play a key role in the stereochemistry of α- and β-d-glucose?
metadata.artigo.dc.creator: Silla, Josué M.
Cormanich, Rodrigo A.
Rittner, Roberto
Freitas, Matheus P.
metadata.artigo.dc.subject: d-Glucose
Hydrogen bond
Natural bond orbital (NBO)
Non-covalent interaction (NCI)
Quantum theory of atoms in molecules (QTAIM)
metadata.artigo.dc.publisher: Elsevier 19-Sep-2014
metadata.artigo.dc.identifier.citation: SILLA, JOSUÉ M. et al. Does intramolecular hydrogen bond play a key role in the stereochemistry of α- and β-d-glucose? Carbohydrate Research, [S.l.], v. 396, p. 9-13, Sept. 2014. DOI: 10.1016/j.carres.2014.06.013.
metadata.artigo.dc.description.abstract: Four 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.
metadata.artigo.dc.language: en_US
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