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Static and Dynamic Properties of 1,1′‐Bi‐2‐naphthol and Its Conjugated Acids and Bases
Author(s) -
Alkorta Ibon,
Cancedda Céline,
Cocinero Emilio José,
Dávalos Juan Z.,
Écija Patrica,
Elguero José,
González Javier,
Lesarri Alberto,
Ramos Rocio,
Reviriego Felipe,
Roussel Christian,
Uriarte Iciar,
Vanthuyne Nicolas
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402686
Subject(s) - chemistry , conjugated system , gas phase , oxygen atom , oxygen , mass spectrometry , phase (matter) , spectroscopy , computational chemistry , molecule , organic chemistry , polymer , chromatography , physics , quantum mechanics
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.