Group electronegativities

Group electronegativities

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.
  1. J.E. Huheey, J. Phys. Chem. 69 (1965) 3284-3291, J. Phys. Chem. 70 (1966) 2086-2092
  2. S.G. Bratsch, J. Chem. Edu. 62 (1985) 101-103


Group electronegativities by different methods
NameSymbolHuheey (1965, -66)Bratsch (1985)
1,1-difluoroethyl‐‐CF2CH32.9
2,4,6-tribromophenyl‐‐C6H2Br32.61
2,4,6-trichlorophenyl‐‐C6H2Cl32.71
2,4,6-trichlorostyryl‐‐CH=CHC6H2Cl32.65
2,4,6-trifluorophenyl‐‐C6H2F32.89
2,4,6-triiodophenyl‐‐C6H2I32.57
2,4,6-trimethylstyryl‐‐CH=CHC6H2(CH3)32.41
2,4,6-trinitrophenyl‐‐C6H2(NO2)33.68
2,4,6-trinitrostyryl‐‐CH=CHC6H2(NO2)33.56
3,5-dibromophenyl‐‐C6H3Br22.57
3,5-dichlorophenyl‐‐C6H3Cl22.64
3,5-dichlorostyryl‐‐CH=CHC6H3Cl22.59
3,5-difluorophenyl‐‐C6H3F22.75
3,5-diiodophenyl‐‐C6H3I22.55
3,5-dimethylstyryl‐‐CH=CHC6H3(CH3)22.43
3,5-dinitrophenyl‐‐C6H3(NO2)23.36
3,5-dinitrostyryl‐‐CH=CHC6H3(NO2)23.16
acetoxy‐‐OCOCH32.952.56
acetyl‐‐COCH32.692.46
allyl‐‐CH2CH=CH22.37
amino‐‐NH22.612.42
azido‐‐N34.423.04
benzenesulfinyl‐‐S(=O)C6H52.7
benzenesulfonyl‐‐S(=O)2C6H52.9
beryllanyl‐‐BeH1.89
boranyl‐‐BH22.09
bromoberyllanyl‐‐BeBr1.94
bromochlorofluoromethyl‐‐CBrClF2.9
bromochloroiodomethyl‐‐CBrClI2.64
bromochloromethyl‐‐CHBrCl2.58
bromoiodomethyl‐‐CHBrI2.47
bromomagnesanyl‐‐MgBr1.73
bromomethyl‐‐CH2Br2.4
bromoxy‐‐OBr3.4
bromyloxy‐‐OBrO23.31
carboxy‐‐COOH3.492.8
chloroberyllanyl‐‐BeCl2.02
chlorofluoromethyl‐‐CHClF2.82
chloromagnesanyl‐‐MgCl1.79
chloromethyl‐‐CH2Cl2.47
chlorosyloxy‐‐OClO4.63.34
chloroxy‐‐OCl3.733.29
chloroxy‐‐OCl4.43.29
chloryloxy‐‐OClO24.83.37
cyanato‐‐OCN4.662.97
cyano‐‐CN3.842.77
di(trifluoromethyl)methyl‐‐CH(CF3)23.19
dibromoboranyl‐‐BBr22.38
dibromomethyl‐‐CHBr22.5
dibromophosphino‐‐PBr22.56
dibromophosphoryl‐‐P(=O)Br23.1
dichloroamino‐‐NCl23.14
dichloroboranyl‐‐BCl22.55
dichloromethyl‐‐CHCl22.66
dichlorophosphino‐‐PCl22.71
dichlorophosphoryl‐‐P(=O)Cl23.3
diethylamino‐‐N(CH2CH3)22.36
diethylphosphino‐‐P(CH2CH3)22.29
difluoroamino‐‐NF23.643.61
difluoroboranyl‐‐BF22.92
difluoromethyl‐‐CHF23
difluorophosphino‐‐PF23.29
difluorophosphoryl‐‐P(=O)F23.8
dihydroxyphosphoryl‐‐P(=O)(OH)23.6
diiodoboranyl‐‐BI22.3
diiodomethyl‐‐CHI22.44
dimethylamino‐‐N(CH3)22.4
dimethylboranyl‐‐B(CH3)22.23
dimethylphosphino‐‐P(CH3)22.28
ethoxy‐‐OCH2CH32.53
ethyl‐‐CH2CH32.272.29
ethylamino‐‐NHCH2CH32.4
ethylsulfanyl‐‐SCH2CH32.39
ethynyl‐‐C≡CH2.9
fluoroberyllanyl‐‐BeF2.16
fluorohydroxy‐‐OF4.14
fluoromagnesanyl‐‐MgF1.87
fluoromethyl‐‐CH2F2.61
formyl‐‐CHO3.142.64
formyloxy‐‐OCHO3.542.8
germanyl‐‐GeH32.32
hydrazino‐‐NHNH22.63
hydroxamino‐‐NHOH3.16
hydroxy‐‐OH3.512.68
hydroxymethyl‐‐CH2OH2.74
iodoberyllanyl‐‐BeI1.91
iodomagnesanyl‐‐MgI1.7
iodomethyl‐‐CH2I2.37
iodyloxy‐‐OIO23.21
isocyanato‐‐NCO4.462.97
isopropyl‐‐CH(CH3)22.28
isothiocyanato‐‐NCS4.172.71
magnesanyl‐‐MgH1.5
mercapto‐‐SH2.322.37
methoxy‐‐OCH32.682.44
methoxycarbonyl‐‐COOCH32.94
methyl‐‐CH32.272.28
methylamino‐‐NHCH32.45
methylberyllanyl‐‐BeCH32.01
methylmagnesanyl‐‐MgCH31.88
methylsulfanyl‐‐SCH32.45
methylsulfinyl‐‐S(=O)CH32.8
methylsulfonyl‐‐S(=O)2CH33.1
nitro‐‐NO24.583.3
nitrooxy‐‐ONO24.583.33
nitroso‐‐NO4.453.23
nitrosooxy‐‐ONO4.433.3
p-bromophenyl‐‐C6H4Br2.53
p-chlorophenyl‐‐C6H4Cl2.56
p-chlorostyryl‐‐CH=CHC6H4Cl2.54
p-fluorophenyl‐‐C6H4F2.55
p-hydroxyphenyl‐‐C6H4OH2.68
p-iodophenyl‐‐C6H4I2.52
p-methylstyryl‐‐CH=CHC6H4CH32.45
p-nitrophenyl‐‐C6H4NO22.98
p-nitrostyryl‐‐CH=CHC6H4NO22.85
pentamethylphenyl‐‐C6(CH3)52.37
pentamethylstyryl‐‐CH=CHC6(CH3)52.38
perchloryloxy‐‐OClO33.38
perfluoroethyl‐‐CF2CF33.4
perfluoroisopropyl‐‐CF(CF3)23.38
phenoxy‐‐OC6H52.44
phenyl‐‐C6H52.492.38
phosphino‐‐PH22.132.2
phosphoroso‐‐PO3.8
silyl‐‐SiH32.212.12
stannyl‐‐SnH32.32
styryl‐‐CH=CHC6H52.48
thiocyanato‐‐SCN3.912.71
tribromogermanyl‐‐GeBr32.58
tribromomethyl‐‐CBr32.59
tribromosilyl‐‐SiBr32.54
tribromostannyl‐‐SnBr32.55
trichlorogermanyl‐‐GeCl32.79
trichloromethyl‐‐CCl32.842.98
trichlorosilyl‐‐SiCl32.78
trichlorostannyl‐‐SnCl32.73
trifluorogermanyl‐‐GeF33.25
trifluoromethoxy‐‐OCF33.74
trifluoromethyl‐‐CF33.463.49
trifluorosilyl‐‐SiF33.353.12
trifluorostannyl‐‐SnF33.11
triiodogermanyl‐‐GeI32.51
triiodomethyl‐‐CI32.51
triiodosilyl‐‐SiI32.46
triiodostannyl‐‐SnI32.49
trimethylgermanyl‐‐Ge(CH3)32.19
trimethylsilyl‐‐Si(CH3)32.27
trimethylstannyl‐‐Sn(CH3)32.3
vinyl‐‐CH=CH22.41