Premium
Investigation of the Hydrogen Bonding Properties of a Series of Monosaccharides in Aqueous Media by 1 H NMR and IR Spectroscopy
Author(s) -
Hawley Joanne,
Bampos Nick,
Aboitiz Nuria,
JiménezBarbero Jesus,
Paz Manuela López de la,
Sanders Jeremy K. M.,
Carmona Pedro,
Vicent Cristina
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200206)2002:12<1925::aid-ejoc1925>3.0.co;2-9
Subject(s) - chemistry , hydrogen bond , intramolecular force , aqueous solution , counterion , intermolecular force , molecule , monosaccharide , proton nmr , nuclear magnetic resonance spectroscopy , ammonium , organic chemistry , ion
A technique, based on 1 H NMR and IR experiments, to characterise intramolecular hydrogen bonds in aqueous medium in a series of amino, amido and ammonium sugar derivatives has been established. Three groups of molecules, representing amides ( 4 , 5 and 6 ), amines ( 7 and 8 ) and ammonium salts (chlorides 9 and 10 , and phosphates 11 and 12 ), with different relative configurations of their functional groups, have been investigated to assess the effect of the nature and the stereochemistry of these groups on the hydrogen‐bonding features of the sugar. The deduced features in water solution are compared to those obtained previously in nonpolar solvents. The phosphate salts of amines 7 and 8 ( 11 and 12 ) were also prepared, in order to evaluate the influence of the OH groups on the binding of the phosphate counterion, and the possibility of establishing cooperative hydrogen bonds involving the phosphate group. The data presented here indicate that the 1,3‐ cis ‐diaxial‐type configuration in sugar diols and amino alcohols produces an intramolecular six ‐ membered ‐ ring hydrogen bond that survives in water and, moreover, offers the possibility to establish cooperative intermolecular hydrogen bonds. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)