Study of the interaction of KF with carbohydrates in DMSO-d6 by 1H and 13C NMR spectroscopy

Pedro Qrtiz, Edilso Reguera, José Fernández-Bertraán

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The interaction of KF with sugars (D-glucose, D-xylose, D-galactose, D-ribose, D-mannose, D-lyxose, cellobiose, maltose, maltotriose, amylose, saccharose and γ-cyclodextrin) were studied by 1H and 13C NMR spectroscopies in DMSO-d6. The main interactions are of the hydrogen bonding type between the sugar hydroxyl protons and the F- anions of KF. The shifts in mutarotation toward the β anomers are due to the breaking of the (OH)1· · ·(OH)2 intramolecular hydrogen bonds by F-, which destabilizes the α form in glucose, xylose, galactose and ribose. KF also attacks and breaks intermolecular hydrogen bond bridges as those observed between (OH)2 and (OH)3′ groups of neighboring hexose units in amylose.

Original languageEnglish
Pages (from-to)7-12
Number of pages6
JournalJournal of Fluorine Chemistry
Volume113
Issue number1
DOIs
StatePublished - 28 Jan 2002
Externally publishedYes

Keywords

  • H and C NMR
  • Hydrogen bonding
  • Mutarotation
  • Potassium fluoride
  • Sugars

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