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2-α-hydroxyalkyl- and 2,7-di(α-hydroxyalkyl)-1,8-bis(dimethylamino)naphthalenes: stabilization of nonconventional in/out conformers of "proton sponges" via N···H-–O intramolecular hydrogen bonding. A remarkable kind of tandem nitrogen inversion.
Autorzy
Rok wydania
2007
Czasopismo
Numer woluminu
72
Strony
3006-3019
DOI
10.1021/jo062667v
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A regular set of 2-(α-hydroxymethyl)- and 2,7-di(α-hydroxymethyl)-1,8-bis(dimethylamino)naphthalenes has been prepared. Their X-ray, NMR, and IR studies have demonstrated that in tertiary mono-alcohols the orientation of free nitrogen electron pairs in crystals and solution corresponds to nonconventional in/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 the parent proton sponge and the majority of its derivatives.
Słowa kluczowe
Alcohols, Diols, Nitrogen, Conformation, Molecular structure
Adres publiczny
https://doi.org/10.1021/jo062667v
Strona internetowa wydawcy
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