title: Static and dynamic properties of 1,1'-bi-2-naphthol and its conjugated acids and bases.
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.
authors.affiliation: Instituto de Química Médica, CSIC, Juan de la Cierva, 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853. ibon@iqm.csic.es.
authors.forename: Ibon
authors.initials: I
authors.lastname: Alkorta
authors.forename: Céline
authors.initials: C
authors.lastname: Cancedda
authors.forename: Emilio José
authors.initials: EJ
authors.lastname: Cocinero
authors.forename: Juan Z
authors.initials: JZ
authors.lastname: Dávalos
authors.forename: Patrica
authors.initials: P
authors.lastname: Ecija
authors.forename: José
authors.initials: J
authors.lastname: Elguero
authors.forename: Javier
authors.initials: J
authors.lastname: González
authors.forename: Alberto
authors.initials: A
authors.lastname: Lesarri
authors.forename: Rocio
authors.initials: R
authors.lastname: Ramos
authors.forename: Felipe
authors.initials: F
authors.lastname: Reviriego
authors.forename: Christian
authors.initials: C
authors.lastname: Roussel
authors.forename: Iciar
authors.initials: I
authors.lastname: Uriarte
authors.forename: Nicolas
authors.initials: N
authors.lastname: Vanthuyne
keywords: acidity; atropisomerism; binaphthol; density functional calculations; rotational spectroscopy