Primary and secondary binding sites for lanthanide shift reagents with amides. Differential behavior of cis vs trans amide isomers with LSR
- 1 July 1980
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 14 (1) , 40-44
- https://doi.org/10.1002/mrc.1270140109
Abstract
Lanthanide induced shifts (LIS) were measured for four dimethylamides, RCON(CH3)2, and four monomethyl amides, RCONHCH3, R H, CH3, CF3 and CCl3, using Eu(fod)3 in CCl4 and benzene (C6D6) solution. Structural correlations for HCON(CH3)2 and CH3CON(CH3)2 in both solvents yield a preferred binding site for the Eu(fod)3 on one of the lone‐pair orbitals of the oxygen atom, with a probable site of secondary importance on the other lone‐pair orbital. The cis vs trans isomers of HCONHCH3 and CH3CONHCH3 exhibit remarkably different chemical shift behavior upon addition of Eu(fod)3.Keywords
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