Literature DB >> 23960019

Intramolecular OH···FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2.

Guy T Giuffredi1, Véronique Gouverneur, Bruno Bernet.   

Abstract

An intramolecular bifurcated H-bond from the axial HO-2 group to the axial F-4 atom and to the O5 atom of α-D-hexopyranosides in apolar solvents is evidenced in (1)H NMR spectra. The H-accepting properties of the F atom are modulated by the orientation of the O-substituent at the C3 atom and by an additional F atom at the C4 atom.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbohydrates; density functional calculations; fluorinated alcohols; hydrogen bonds; scalar couplings

Mesh：

Substances：

Year:  2013        PMID： 23960019     DOI： 10.1002/anie.201303766

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Influence of Fluorination on the Conformational Properties and Hydrogen-Bond Acidity of Benzyl Alcohol Derivatives.

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2.  A Study of Intramolecular Hydrogen Bonding in Levoglucosan Derivatives.

Authors:  Lucas Quiquempoix; Elena Bogdan; Neil J Wells; Jean-Yves Le Questel; Jérôme Graton; Bruno Linclau
Journal:  Molecules       Date:  2017-03-24       Impact factor: 4.411

3.  3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation.

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Review 4.  Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F).

Authors:  Louise Ruyet; Tatiana Besset
Journal:  Beilstein J Org Chem       Date:  2020-05-18       Impact factor: 2.883

5.  The role of intermolecular interactions in stabilizing the structure of the nematic twist-bend phase.

Authors:  Katarzyna Merkel; Barbara Loska; Chris Welch; Georg H Mehl; Antoni Kocot
Journal:  RSC Adv       Date:  2021-01-13       Impact factor: 3.361

6.  Understanding the effects of vicinal carbon substituents and configuration on organofluorine hydrogen-bonding interaction.

Authors:  Qingqing Jia; Qingzhong Li; Mo Luo; Hai-Bei Li
Journal:  RSC Adv       Date:  2018-11-20       Impact factor: 3.361

7.  Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane.

Authors:  Pier Alexandre Champagne; Alexandre Saint-Martin; Mélina Drouin; Jean-François Paquin
Journal:  Beilstein J Org Chem       Date:  2013-11-13       Impact factor: 2.883

8.  Intramolecular OH⋅⋅⋅Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif.

Authors:  Bruno Linclau; Florent Peron; Elena Bogdan; Neil Wells; Zhong Wang; Guillaume Compain; Clement Q Fontenelle; Nicolas Galland; Jean-Yves Le Questel; Jérôme Graton
Journal:  Chemistry       Date:  2015-10-23       Impact factor: 5.236
  8 in total

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