Introduction
Although electronegativity according to its original definition by Pauling is a property of an element it
is such a useful concept that attempts have been made to apply it to functional groups as well.
The electronegativity of functional groups can be estimated using a number of different approaches.
The values shown here are computed using the assumption of electronegativity
equalization. A key feature of group electronegativities is that they are not constant but vary depending on their surrounding.
They can be seen as a complement to Hammett-type parameters when describing functional
group polarity but are less versatile.
- J.E. Huheey, J. Phys. Chem. 69 (1965) 3284-3291,
J. Phys. Chem. 70 (1966) 2086-2092
- S.G. Bratsch, J. Chem. Edu. 62 (1985) 101-103
Group electronegativities by different methodsName | Symbol | Huheey (1965, -66) | Bratsch (1985) |
---|
1,1-difluoroethyl‐ | ‐CF2CH3 | 2.9 | |
2,4,6-tribromophenyl‐ | ‐C6H2Br3 | 2.61 | |
2,4,6-trichlorophenyl‐ | ‐C6H2Cl3 | 2.71 | |
2,4,6-trichlorostyryl‐ | ‐CH=CHC6H2Cl3 | 2.65 | |
2,4,6-trifluorophenyl‐ | ‐C6H2F3 | 2.89 | |
2,4,6-triiodophenyl‐ | ‐C6H2I3 | 2.57 | |
2,4,6-trimethylstyryl‐ | ‐CH=CHC6H2(CH3)3 | 2.41 | |
2,4,6-trinitrophenyl‐ | ‐C6H2(NO2)3 | 3.68 | |
2,4,6-trinitrostyryl‐ | ‐CH=CHC6H2(NO2)3 | 3.56 | |
3,5-dibromophenyl‐ | ‐C6H3Br2 | 2.57 | |
3,5-dichlorophenyl‐ | ‐C6H3Cl2 | 2.64 | |
3,5-dichlorostyryl‐ | ‐CH=CHC6H3Cl2 | 2.59 | |
3,5-difluorophenyl‐ | ‐C6H3F2 | 2.75 | |
3,5-diiodophenyl‐ | ‐C6H3I2 | 2.55 | |
3,5-dimethylstyryl‐ | ‐CH=CHC6H3(CH3)2 | 2.43 | |
3,5-dinitrophenyl‐ | ‐C6H3(NO2)2 | 3.36 | |
3,5-dinitrostyryl‐ | ‐CH=CHC6H3(NO2)2 | 3.16 | |
acetoxy‐ | ‐OCOCH3 | 2.95 | 2.56 |
acetyl‐ | ‐COCH3 | 2.69 | 2.46 |
allyl‐ | ‐CH2CH=CH2 | 2.37 | |
amino‐ | ‐NH2 | 2.61 | 2.42 |
azido‐ | ‐N3 | 4.42 | 3.04 |
benzenesulfinyl‐ | ‐S(=O)C6H5 | 2.7 | |
benzenesulfonyl‐ | ‐S(=O)2C6H5 | 2.9 | |
beryllanyl‐ | ‐BeH | 1.89 | |
boranyl‐ | ‐BH2 | 2.09 | |
bromoberyllanyl‐ | ‐BeBr | 1.94 | |
bromochlorofluoromethyl‐ | ‐CBrClF | 2.9 | |
bromochloroiodomethyl‐ | ‐CBrClI | 2.64 | |
bromochloromethyl‐ | ‐CHBrCl | 2.58 | |
bromoiodomethyl‐ | ‐CHBrI | 2.47 | |
bromomagnesanyl‐ | ‐MgBr | 1.73 | |
bromomethyl‐ | ‐CH2Br | 2.4 | |
bromoxy‐ | ‐OBr | 3.4 | |
bromyloxy‐ | ‐OBrO2 | | 3.31 |
carboxy‐ | ‐COOH | 3.49 | 2.8 |
chloroberyllanyl‐ | ‐BeCl | 2.02 | |
chlorofluoromethyl‐ | ‐CHClF | 2.82 | |
chloromagnesanyl‐ | ‐MgCl | 1.79 | |
chloromethyl‐ | ‐CH2Cl | 2.47 | |
chlorosyloxy‐ | ‐OClO | 4.6 | 3.34 |
chloroxy‐ | ‐OCl | 3.73 | 3.29 |
chloroxy‐ | ‐OCl | 4.4 | 3.29 |
chloryloxy‐ | ‐OClO2 | 4.8 | 3.37 |
cyanato‐ | ‐OCN | 4.66 | 2.97 |
cyano‐ | ‐CN | 3.84 | 2.77 |
di(trifluoromethyl)methyl‐ | ‐CH(CF3)2 | 3.19 | |
dibromoboranyl‐ | ‐BBr2 | 2.38 | |
dibromomethyl‐ | ‐CHBr2 | 2.5 | |
dibromophosphino‐ | ‐PBr2 | 2.56 | |
dibromophosphoryl‐ | ‐P(=O)Br2 | 3.1 | |
dichloroamino‐ | ‐NCl2 | 3.14 | |
dichloroboranyl‐ | ‐BCl2 | 2.55 | |
dichloromethyl‐ | ‐CHCl2 | 2.66 | |
dichlorophosphino‐ | ‐PCl2 | 2.71 | |
dichlorophosphoryl‐ | ‐P(=O)Cl2 | 3.3 | |
diethylamino‐ | ‐N(CH2CH3)2 | 2.36 | |
diethylphosphino‐ | ‐P(CH2CH3)2 | 2.29 | |
difluoroamino‐ | ‐NF2 | 3.64 | 3.61 |
difluoroboranyl‐ | ‐BF2 | 2.92 | |
difluoromethyl‐ | ‐CHF2 | 3 | |
difluorophosphino‐ | ‐PF2 | 3.29 | |
difluorophosphoryl‐ | ‐P(=O)F2 | 3.8 | |
dihydroxyphosphoryl‐ | ‐P(=O)(OH)2 | 3.6 | |
diiodoboranyl‐ | ‐BI2 | 2.3 | |
diiodomethyl‐ | ‐CHI2 | 2.44 | |
dimethylamino‐ | ‐N(CH3)2 | 2.4 | |
dimethylboranyl‐ | ‐B(CH3)2 | 2.23 | |
dimethylphosphino‐ | ‐P(CH3)2 | 2.28 | |
ethoxy‐ | ‐OCH2CH3 | 2.53 | |
ethyl‐ | ‐CH2CH3 | 2.27 | 2.29 |
ethylamino‐ | ‐NHCH2CH3 | 2.4 | |
ethylsulfanyl‐ | ‐SCH2CH3 | 2.39 | |
ethynyl‐ | ‐C≡CH | 2.9 | |
fluoroberyllanyl‐ | ‐BeF | 2.16 | |
fluorohydroxy‐ | ‐OF | 4.14 | |
fluoromagnesanyl‐ | ‐MgF | 1.87 | |
fluoromethyl‐ | ‐CH2F | 2.61 | |
formyl‐ | ‐CHO | 3.14 | 2.64 |
formyloxy‐ | ‐OCHO | 3.54 | 2.8 |
germanyl‐ | ‐GeH3 | 2.32 | |
hydrazino‐ | ‐NHNH2 | 2.63 | |
hydroxamino‐ | ‐NHOH | 3.16 | |
hydroxy‐ | ‐OH | 3.51 | 2.68 |
hydroxymethyl‐ | ‐CH2OH | 2.74 | |
iodoberyllanyl‐ | ‐BeI | 1.91 | |
iodomagnesanyl‐ | ‐MgI | 1.7 | |
iodomethyl‐ | ‐CH2I | 2.37 | |
iodyloxy‐ | ‐OIO2 | | 3.21 |
isocyanato‐ | ‐NCO | 4.46 | 2.97 |
isopropyl‐ | ‐CH(CH3)2 | 2.28 | |
isothiocyanato‐ | ‐NCS | 4.17 | 2.71 |
magnesanyl‐ | ‐MgH | 1.5 | |
mercapto‐ | ‐SH | 2.32 | 2.37 |
methoxy‐ | ‐OCH3 | 2.68 | 2.44 |
methoxycarbonyl‐ | ‐COOCH3 | 2.94 | |
methyl‐ | ‐CH3 | 2.27 | 2.28 |
methylamino‐ | ‐NHCH3 | 2.45 | |
methylberyllanyl‐ | ‐BeCH3 | 2.01 | |
methylmagnesanyl‐ | ‐MgCH3 | 1.88 | |
methylsulfanyl‐ | ‐SCH3 | 2.45 | |
methylsulfinyl‐ | ‐S(=O)CH3 | 2.8 | |
methylsulfonyl‐ | ‐S(=O)2CH3 | 3.1 | |
nitro‐ | ‐NO2 | 4.58 | 3.3 |
nitrooxy‐ | ‐ONO2 | 4.58 | 3.33 |
nitroso‐ | ‐NO | 4.45 | 3.23 |
nitrosooxy‐ | ‐ONO | 4.43 | 3.3 |
p-bromophenyl‐ | ‐C6H4Br | 2.53 | |
p-chlorophenyl‐ | ‐C6H4Cl | 2.56 | |
p-chlorostyryl‐ | ‐CH=CHC6H4Cl | 2.54 | |
p-fluorophenyl‐ | ‐C6H4F | 2.55 | |
p-hydroxyphenyl‐ | ‐C6H4OH | 2.68 | |
p-iodophenyl‐ | ‐C6H4I | 2.52 | |
p-methylstyryl‐ | ‐CH=CHC6H4CH3 | 2.45 | |
p-nitrophenyl‐ | ‐C6H4NO2 | 2.98 | |
p-nitrostyryl‐ | ‐CH=CHC6H4NO2 | 2.85 | |
pentamethylphenyl‐ | ‐C6(CH3)5 | 2.37 | |
pentamethylstyryl‐ | ‐CH=CHC6(CH3)5 | 2.38 | |
perchloryloxy‐ | ‐OClO3 | | 3.38 |
perfluoroethyl‐ | ‐CF2CF3 | 3.4 | |
perfluoroisopropyl‐ | ‐CF(CF3)2 | 3.38 | |
phenoxy‐ | ‐OC6H5 | | 2.44 |
phenyl‐ | ‐C6H5 | 2.49 | 2.38 |
phosphino‐ | ‐PH2 | 2.13 | 2.2 |
phosphoroso‐ | ‐PO | 3.8 | |
silyl‐ | ‐SiH3 | 2.21 | 2.12 |
stannyl‐ | ‐SnH3 | 2.32 | |
styryl‐ | ‐CH=CHC6H5 | 2.48 | |
thiocyanato‐ | ‐SCN | 3.91 | 2.71 |
tribromogermanyl‐ | ‐GeBr3 | 2.58 | |
tribromomethyl‐ | ‐CBr3 | 2.59 | |
tribromosilyl‐ | ‐SiBr3 | 2.54 | |
tribromostannyl‐ | ‐SnBr3 | 2.55 | |
trichlorogermanyl‐ | ‐GeCl3 | 2.79 | |
trichloromethyl‐ | ‐CCl3 | 2.84 | 2.98 |
trichlorosilyl‐ | ‐SiCl3 | 2.78 | |
trichlorostannyl‐ | ‐SnCl3 | 2.73 | |
trifluorogermanyl‐ | ‐GeF3 | 3.25 | |
trifluoromethoxy‐ | ‐OCF3 | 3.74 | |
trifluoromethyl‐ | ‐CF3 | 3.46 | 3.49 |
trifluorosilyl‐ | ‐SiF3 | 3.35 | 3.12 |
trifluorostannyl‐ | ‐SnF3 | 3.11 | |
triiodogermanyl‐ | ‐GeI3 | 2.51 | |
triiodomethyl‐ | ‐CI3 | 2.51 | |
triiodosilyl‐ | ‐SiI3 | 2.46 | |
triiodostannyl‐ | ‐SnI3 | 2.49 | |
trimethylgermanyl‐ | ‐Ge(CH3)3 | 2.19 | |
trimethylsilyl‐ | ‐Si(CH3)3 | 2.27 | |
trimethylstannyl‐ | ‐Sn(CH3)3 | 2.3 | |
vinyl‐ | ‐CH=CH2 | 2.41 | |