Hammett Sigma Constants*
Group | σmeta | σpara | σI | σv | π | Es | MR |
---|---|---|---|---|---|---|---|
H | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 1.03 |
CH3 | -0.07 | -0.17 | -0.04 | 0.52 | 0.56 | -1.24 | 5.65 |
C2H5 | -0.07 | -0.15 | -0.05 | 0.56 | 1.02 | -1.31 | 10.30 |
n-C3H7 | -0.07 | -0.13 | -0.03 | 0.68 | 1.55 | -1.60 | 14.96 |
i-C3H7 | -0.07 | -0.15 | -0.03 | 0.76 | 1.53 | -1.71 | 14.96 |
n-C4H9 | -0.08 | -0.16 | -0.04 | 0.68 | 2.13 | -1.63 | 19.61 |
t-C4H9 | -0.10 | -0.20 | -0.07 | 1.24 | 1.98 | -2.78 | 19.62 |
H2C=CH** | 0.05 | -0.02 | 0.09 | 2.11 | 0.82 | 10.99 | |
C6H5** | 0.06 | -0.01 | 0.10 | 2.15 | 1.96 | -3.82 | 25.36 |
CH2Cl | 0.11 | 0.12 | 0.15 | 0.60 | 0.17 | -1.48 | 10.49 |
CF3 | 0.43 | 0.54 | 0.42 | 0.91 | 0.88 | -2.40 | 5.02 |
CN | 0.56 | 0.66 | 0.53 | 0.40 | -0.57 | -0.51 | 6.33 |
CHO | 0.35 | 0.42 | 0.25 | -0.65 | 6.88 | ||
COCH3 | 0.38 | 0.50 | 0.29 | 0.50 | -0.55 | 11.18 | |
CO2H** | 0.37 | 0.45 | 0.39 | 1.45 | -0.32 | 6.93 | |
Si(CH3)3 | -0.04 | -0.07 | -0.13 | 1.40 | 2.59 | 24.96 | |
F | 0.34 | 0.06 | 0.52 | 0.27 | 0.14 | -0.46 | 0.92 |
Cl | 0.37 | 0.23 | 0.47 | 0.55 | 0.71 | -0.97 | 6.03 |
Br | 0.39 | 0.23 | 0.50 | 0.65 | 0.86 | -1.16 | 8.88 |
I | 0.35 | 0.18 | 0.39 | 0.78 | 1.12 | -1.40 | 13.94 |
OH | 0.12 | -0.37 | 0.29 | 0.32 | -0.67 | -0.55 | 2.85 |
OCH3 | 0.12 | -0.27 | 0.27 | 0.36 | -0.02 | -0.55 | 7.87 |
OCH2CH3 | 0.10 | -0.24 | 0.27 | 0.48 | 0.38 | 12.47 | |
SH | 0.25 | 0.15 | 0.26 | 0.60 | 0.39 | -1.07 | 9.22 |
SCH3 | 0.15 | 0.00 | 0.23 | 0.64 | 0.61 | -1.07 | 13.82 |
NO2** | 0.71 | 0.78 | 0.76 | 1.39 | -0.28 | -2.52 | 7.36 |
NO | 0.62 | 0.91 | 0.37 | -0.12 | 5.20 | ||
NH2 | -0.16 | -0.66 | 0.12 | -1.23 | -0.61 | 5.42 | |
NHCHO | 0.19 | 0.00 | 0.27 | -0.98 | 10.31 | ||
NHCOCH3 | 0.07 | -0.15 | 0.26 | -0.37 | 16.53 | ||
N(CH3)2 | -0.15 | -0.83 | 0.06 | 0.43 | 0.18 | 15.55 | |
N(CH3)3+ | 0.88 | 0.82 | 0.93 | 1.22 | -5.96 | 21.20 |
* σmeta, σpara = Hammett constants; σI = inductive sigma constant; σv = Charton's v (size) values; p = hydrophobicity parameter; Es = Taft size parameter; MR = molar refractivity (polarizability) parameter.
** indicates that the group is in the most sterically hindered conformation.
Reference: C. Hansch and A. Leo, "Substituent Constants for Correlation Analysis in Chemistry and Biology," Wiley-Interscience, NY, 1979.