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Updated: Apr 23, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Static and dynamic properties of 1,1'-bi-2-naphthol and its conjugated acids and bases
Ibon Alkorta1, Céline Cancedda, Emilio José Cocinero
1Instituto de Química Médica, CSIC, Juan de la Cierva, 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853. ibon@iqm.csic.es.
Abstract:
Several convergent techniques were used to characterize 1,1'-bi-2-naphthol (BINOL) and some of its properties. Its acidity in the gas-phase, from neutral species to monoanion, was measured by mass spectrometry. The conformation and structure of BINOL in the gas phase was determined by microwave rotational spectroscopy. NMR experiments in fluorosulfonic acid established that BINOL was monoprotonated on one of the hydroxyl oxygen atoms. The enantiomerization barriers reported in the literature for BINOL under neutral, basic, and acid conditions were analyzed with regard to the species involved. Finally, DFT calculations allowed all of these results to be gathered in a coherent picture of the BINOL structure.
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