Abstract
Undergraduate texts commonly discuss the anisochrony (non-coincidence of NMR signals) of methylene protons near chiral center using projections in which the chiral center and the carbon bearing the methylene protons are separated by a single bond. An analysis of the various rotational conformers about this bond demonstrate the non equality of the protons in question and reinforces the fact that the chemical shift for a given proton is the weighted average for the proton in its various conformations. N-substituted derivatives of the alpha-aminobenzenebutanenitrile system and alpha-methyaminopropanenitrile are obtained by easy one step syntheses. During the characterization of these compounds, which have two consecutive methylene groups attached to their chiral center, we were surprised to observe that although both pairs of methylene protons are diastereotopic and therefore anisochronous, only the gamma protons actually displayed different chemical shifts. The s protons, which are separated from the chiral...
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