Secondary phosphine oxides: tautomerism and chiral recognition monitored by multinuclear NMR spectroscopy of their Rh 2 [( R )‐MTPA] 4  adducts | Zendy

Magiera Damian | Zendy; Szmigielska Anna | Zendy; Pietrusiewicz K. Michal | Zendy; Duddeck Helmut | Zendy

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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.

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