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Secondary phosphine oxides: tautomerism and chiral recognition monitored by multinuclear NMR spectroscopy of their Rh 2 [( R )‐MTPA] 4 adducts
Author(s) -
Magiera Damian,
Szmigielska Anna,
Pietrusiewicz K. Michal,
Duddeck Helmut
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10306
Subject(s) - chemistry , phosphine , tautomer , adduct , enantiomer , nuclear magnetic resonance spectroscopy , solvent , ligand (biochemistry) , chirality (physics) , molecule , acetone , proton nmr , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , nambu–jona lasinio model , receptor , chiral symmetry breaking , physics , quantum mechanics , quark
Six secondary phosphine oxides and their tautomeric equilibria as free ligands and in the presence of an equimolar amount of the chiral dirhodium complex Rh* are described and discussed. Discrimination of enantiomers is easily possible by inspecting the 31 P NMR resonances; some 1 H and 13 C NMR resonances are useful as well. H/D exchange of the acidic protons in the phosphine oxides takes place with acetone‐d 6 , the solvent additive, after some hours but does not obscure the chiral recognition experiment. 103 Rh, 31 P coupling constants are discussed briefly. Decomposition of ligand molecules in 1:1‐Rh*‐ adducts occurs slowly but completely. Chirality 16:57–64, 2004. © 2003 Wiley‐Liss, Inc.