The kinetic acidity of oligofluorobenzenes correlated with their gas phase deprotonation energies

The relative reactivities of fluorobenzene, all di-, tri-, and tetrafluorobenzenes and pentafluorobenzene toward sec-butyllithium have been assessed in THF at -100 DegC. At this temp. no subsequent transmetalation reactions take place but those compromise the outcome of the competition expts. if the latter are conducted at -75 Deg. The rates detd. at -100 Deg reflect the basicity differences between the naked (oligo)fluorophenyl anions to the extent of 10%. [on SciFinder (R)]


Published in:
Chemistry - A European Journal, 11, 11, 3449-3454
Year:
2005
Keywords:
Note:
CAN 143:133044 22-12 Physical Organic Chemistry Institute for Chemical Sciences and Engineering,Ecole Polytechnique Federale (EPFL, BCh),Lausanne,Switz. Journal 0947-6539 written in English. 66186-10-5; 124020-65-1; 150295-36-6; 177267-59-3; 177267-67-3; 181320-43-4; 848933-91-5; 848933-93-7; 848933-95-9; 848933-97-1; 848933-98-2 Role: FMU (Formation, unclassified), PRP (Properties), FORM (Formation, nonpreparative) (kinetic acidity of oligofluorobenzenes correlated with their gas phase deprotonation energies); 327-54-8; 363-72-4; 367-11-3 (1,2-Difluorobenzene); 367-23-7; 372-18-9 (1,3-Difluorobenzene); 372-38-3; 462-06-6 (Fluorobenzene); 540-36-3; 551-62-2; 1489-53-8 (1,2,3-Trifluorobenzene); 2367-82-0 Role: PRP (Properties), RCT (Reactant), RACT (Reactant or reagent) (kinetic acidity of oligofluorobenzenes correlated with their gas phase deprotonation energies); 598-30-1 (sec-Butyl lithium) Role: RGT (Reagent), RACT (Reactant or reagent) (kinetic acidity of oligofluorobenzenes correlated with their gas phase deprotonation energies)
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 Record created 2006-03-03, last modified 2018-12-03


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