A new NMR approach for the assignment of symmetric isomers

Journal of the American Chemical Society
Lodovico Lunazzi, Andrea Mazzanti

Abstract

Irradiation of the (13)C satellite (1% natural abundance) of the NMR (1)H signals yields NOE effects on the spatially close hydrogens of the same isotopomer but not on the hydrogens of the 99% isotopomer having only (12)C atoms. In a DPFGSE-NOE sequence, the latter signals are completely canceled, and it is possible, therefore, to detect NOE effects experienced by isochronous lines that would not be otherwise observable. This allows the structural assignments of symmetric isomers to be unambiguously obtained. Examples are reported for the cases of the cis and trans dimethylstilbene, cis and trans stilbeneoxide, 2,5- and 3,4-dimethylthiophene, 1,8- and 1,5-dimethylnaphthalene, syn and anti 1,2-bis(2-methyl-1-naphthyl)benzene, 1,3-cyclooctadiene, and cycloheptatriene.

Citations

Jun 14, 2017·The Journal of Organic Chemistry·Michele MancinelliAndrea Mazzanti
Nov 11, 2008·Magnetic Resonance in Chemistry : MRC·Pau NolisTeodor Parella
Feb 19, 2008·The Journal of Organic Chemistry·Lodovico LunazziAndrea Mazzanti
Jan 31, 2009·The Journal of Organic Chemistry·Lodovico LunazziAndrea Mazzanti
Jun 15, 2007·The Journal of Organic Chemistry·Lodovico LunazziAndrea Mazzanti
Mar 6, 2012·The Journal of Organic Chemistry·Lodovico LunazziAndrea Mazzanti
Mar 10, 2007·The Journal of Organic Chemistry·Paloma VidalJuan F Espinosa

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