ChemInform Abstract: ELECTROPHILIC AROMATIC SUBSTITUTION. PART XVII. PROTIODETRITIATION OF SOME CYCLOALKYL- AND SECONDARY ALKYL-BENZENES. A LINEAR FREE ENERGY RELATION FOR ORTHO-AROMATIC SUBSTITUTION

1976 ◽  
Vol 7 (26) ◽  
pp. no-no
Author(s):  
M. M. JEAN LE GUEN ◽  
ROGER TAYLOR
Keyword(s):  
Free Energy ◽  
Electrophilic Aromatic Substitution ◽  
Energy Relation ◽  
Aromatic Substitution ◽  
Linear Free Energy ◽  
Free Energy Relation ◽  
Alkyl Benzenes

The transmission of polar effects. Part VI. The ionization of ortho-substituted benzoic acids

1968 ◽  
Vol 46 (18) ◽  
pp. 2941-2944 ◽  
Author(s):  
Keith Bowden ◽  
G. E. Manser
Keyword(s):  
Free Energy ◽  
Benzoic Acid ◽  
Field Effect ◽  
Energy Relation ◽  
Benzoic Acids ◽  
Linear Free Energy ◽  
Free Energy Relation ◽  
Substituted Benzoic Acids ◽  
Reaction Constants

The pKa values of a series of ortho-substituted benzoic acids in 50% ethanol–water have been determined. The effect of ortho-substitution on the ionization of benzoic acid in this and other solvents has been correlated by a linear free energy relation. The reaction constants found are compared with those for the meta/para-substituted benzoic acids. While those for the former system are insensitive to changes in the medium, the latter vary considerably. It is suggested that this is due to transmission by the field effect passing almost entirely through the molecular cavity for ortho-substituents.

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