Effect of Substituents on Aromatic Substitution

Substituents in Order of Decreasing Reactivity of Ring

Substituent Position of
Reaction
log(rate
relative to H)
NR2 o, p 1.3
OH, OR o, p 0.9
R o, p 0.3
Ar o, p 0.2
F o, p 0.1
H "o, p" 0
NHCOR o, p -0.1
Cl, Br, I o, p -0.1
CO2H m -0.4
COR, CO2R m -0.5
CX3 m -0.5
SO3H m -0.6
CN m -0.7
NO2 m -0.8
NR3+ m -0.9