
TY  - JOUR
A1  - Wells, PR 
A1  - Adcock, W 
T1  - Substituent effects in naphthalene. II. The strengths of the 4, 5, 6, 7, and 8-substituted 2-naphthoic acids
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1965
VL  - 18
IS  - 9
SP  - 1365
EP  - 1376
KW  - 
UR  - https://doi.org/10.1071/CH9651365 
N2  - The apparent pKa values of 44 substituted 2-naphthoic acids, six substituted 1-naphthoic acids, and the unsubstituted naphthoic acids have been determined for 50% v/v aqueous ethanol at 25°. The &#916;pK values are examined in terms of Dewar and Grisdale's simple expression for aromatic substituent effects. This expression proves to be fairly satisfactory, but takes no account of substituent dipole orientation, secondary resonance effects, nor &#960;-inductive effects. A survey of the naphthoic acid strengths demonstrates the importance of these factors. In particular, unambiguous evidence for the important role played by direct electrostatic interactions is obtained. 
ER  -

