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2-α-hydroxybenzhydryl- and 2,7-di(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes: the first examples of stabilization of in/out proton sponge conformers by intramolecular hydrogen bonding. The most flattened amino group ever participating in IHB.
Autorzy
Rok wydania
2005
Czasopismo
Numer woluminu
46
Strony
3973-3976
DOI
10.1016/j.tetlet.2005.04.045
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
2-(α-Hydroxybenzhydryl)- 6 and 2,7-di(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes 8 have been shown to exist in crystals as in/out conformers stabilized by O–H⋯N intramolecular hydrogen bonding. In agreement with X-ray studies, the NMR data are also consistent with 7 retaining its in/out form in solution, whilst for 8 superimposed equilibrating in/out–out/in conformers are observed.
Adres publiczny
https://doi.org/10.1016/j.tetlet.2005.04.045
Strona internetowa wydawcy
Podobne publikacje
2007
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.
Pozharskii Alexander F., Degtyarev A. V., Ryabtsova O. V., Ozeryanskii Valery A., Kletskii M. E., Starikova Z. A., Sobczyk Lucjan, Filarowski Aleksander