| Abstract
| - A regular set of 2-(α-hydroxymethyl)- and 2,7-di(α-hydroxymethyl)-1,8-bis(dimethylamino)naphthaleneshas been prepared. Their X-ray, NMR, and IR studies have demonstrated that in tertiary mono-alcoholsthe orientation of free nitrogen electron pairs in crystals and solution corresponds to nonconventionalin/out conformers stabilized by O−H···N intramolecular hydrogen bonding. For tertiary 2,7-dialcohols,the superimposed equilibrating in/out−out/in nitrogen invertomers are observed in solution. Unlike this,primary and secondary mono- and dialcohols commonly exist in the in/in form, which is typical for theparent proton sponge and the majority of its derivatives.
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