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The Kinetic Acidity of Oligofluorobenzenes Correlated with Their Gas Phase Deprotonation Energies
Author(s) -
Schlosser Manfred,
Marzi Elena
Publication year - 2005
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.200401094
Subject(s) - fluorobenzene , deprotonation , chemistry , tetrahydrofuran , transmetalation , gas phase , kinetic energy , medicinal chemistry , phase (matter) , photochemistry , organic chemistry , benzene , catalysis , solvent , ion , physics , quantum mechanics
Abstract The relative reactivities of fluorobenzene, all di‐, tri‐, and tetrafluorobenzenes and pentafluorobenzene toward sec ‐butyllithium have been assessed in tetrahydrofuran at −100 °C. At this temperature no subsequent transmetalation reactions take place but those compromise the outcome of the competition experiments if the latter are conducted at −75 °C. The rates determined at −100 °C reflect the basicity differences between the naked (oligo)fluorophenyl anions to the extent of 10 %.