24476-07-1Relevant articles and documents
Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring
Kozlecki, Tomasz,Tolstoy, Peter M.,Kwocz, Agnieszka,Vovk, Mikhail A.,Kochel, Andrzej,Polowczyk, Izabela,Tretyakov, Peter Yu.,Filarowski, Aleksander
, p. 254 - 262 (2015)
Three β-hydroxynaphthylamides (morpholine, pyrrolidine and dimethylamine derivatives) have been synthesized and their conformational state was analyzed by NMR, X-ray and DFT calculations. In aprotic solution the molecules contain intramolecular OHO hydrogen bonds, which change into intermolecular ones in solid state. The energy barriers for the amide group rotation around the CN bond were estimated from the line shape analysis of 1H and 13C NMR signals. A tentative correlation between the barrier height and the strength of OHO bond was proposed. Calculations of the potential energy profiles for the rotations around CC and CN bonds were done. In case of morpholine derivative experimental indications of additional dynamics: chair-chair 'ring flip' in combination with the twisting around CC bond were obtained and confirmed by quantum chemistry calculations.
Photochemical generation and the reactivity of o-naphthoquinone methides in aqueous solutions
Arumugam, Selvanathan,Popik, Vladimir V.
, p. 11892 - 11899 (2009)
Irradiation of 3-hydroxy-2-naphthalenemethanol (3a) and 2-hydroxy-1-naphthalenemethanol (4a) results in efficient (Φ254 ) 0.17 and 0.20) dehydration and the formation of isomeric naphthoquinone methides, 2,3-naphthoquinone-3-methide (1) and 1,2
