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Metal ion complexation by the phosphoryl and the carbonyl groups probed by 17 O NMR spectroscopy
Author(s) -
Belciug MarieP.,
Modro Agnes M.,
Modro Tomasz A.,
Wessels Philippus L.
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080906
Subject(s) - chemistry , intramolecular force , chelation , nuclear magnetic resonance spectroscopy , metal , spectroscopy , metal ions in aqueous solution , hydrogen bond , inorganic chemistry , metal carbonyl , ion , medicinal chemistry , crystallography , stereochemistry , molecule , organic chemistry , physics , quantum mechanics
Interactions between compounds containing phosphoryl, carbonyl, or hydroxyl groups (or combinations of these groups) with metal ions (Na + , Mg 2+ ) were probed in CD 3 CN solutions by 17 O NMR spectroscopy. For all phosphoryl and carbonyl substrates a strong high—field shift of the PO and CO signals was observed on the addition of a salt; no shift was observed, however, for the OH group signal, indicating that no chelation takes place in the hydroxyphosphoryl (or hydroxycarbonyl) derivatives. For 2‐hydroxy‐3‐benzoylpropylphosphonic diester the 17 O NMR studies, together with conformational analysis based on the 1 H spectroscopy, demonstrated the chelation of a metal ion by the PO and CO functions (fermation of an eight–membered cyclic structure) with the OH group involved in the intramolecular hydrogen bonding, but not in the complexation to the metal ion.