Despite ideal conformation of the two naphthyl esters 1a, b in the solid state, they do not form any edge-to-face associates with 9-ethyladenine in solution. Rather, as detailed NOE and 2D-NOESY NMR measurements have shown, face-to-face associates such as 2 are preferentially formed by stacking interactions, whereby the nature of the base pairing and the bond strengths can be engineered as desired by variation of the substituents.
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Rebek et al. (1987) studied this question.