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The Torsional Barriers of 2‐Hydroxy‐ and 2‐Fluorobiphenyl: Small but Measurable
Author(s) -
Mazzanti Andrea,
Lunazzi Lodovico,
Ruzziconi Renzo,
Spizzichino Sara,
Schlosser Manfred
Publication year - 2010
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.200903372
Subject(s) - aryl , ab initio , chemistry , spectroscopy , measure (data warehouse) , nuclear magnetic resonance spectroscopy , position (finance) , crystallography , internal rotation , computational chemistry , stereochemistry , physics , organic chemistry , quantum mechanics , engineering , data mining , mechanical engineering , alkyl , computer science , finance , economics
By making use of a novel diastereotopicity probe, namely C(CF 3 ) 2 OH, it has been possible to measure by very low temperature 19 F NMR spectroscopy the elusive aryl–aryl rotation barriers of biphenyls bearing an OH or F group in one ortho position. The experimental values (5.4 and 4.4 kcal mol −1 , respectively) are matched by those from ab initio calculations (5.3 and 4.3 kcal mol −1 , respectively).