Long-Range Shielding Effects in the 1H NMR Spectra of Mosher-like Ester Derivatives
Year: 2010
Type: article
Abstract: The relative magnitudes of the chemical shift differences (Deltadeltas) in the two diastereomers of menthyl esters of known chiral derivatizing agents (CDAs) were compared to those of the alpha-methoxy-alpha-trifluoromethyl-1-naphthylacetyl (MTN((1))A) analogues I. Discrimination of the terminal diastereotopic methyl resonances in esters of the homologous, symmetrical carbinols II was evaluated. Remarkably, the methyls differed in the MTN((1))A esters III even when n = 15; an unexpected crossover in the sign of the Deltadelta values was also observed.
Source: Organic Letters
DOI: 10.1021/ol1003862
Institution: University of Minnesota
Language: English
Subfield: Spectroscopy
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W1990844730