Professional Documents
Culture Documents
The first part of this table lists substituent groups and their line
formulas. A substituent group is defined by IUPAC as a group
that replaces one or more hydrogen atoms attached to a parent
structure. Such groups are sometimes called radicals, but IUPAC
now reserves the term radical for a free molecular species with
unpaired electrons. IUPAC does not recommend some of these
names, which are marked here with asterisks (e.g., amyl*), but
they are included in this list because they are often encountered
in the older literature. Substituent group names which are formed
Substituent Groups
acetamido (acetylamino)
acetoacetyl
acetonyl
acetyl
acryloyl* (1-oxo-2-propenyl)
alanyl (from alanine)
-alanyl
allyl (2-propenyl)
allylidene (2-propenylidene)
amidino (aminoiminomethyl)
amino
amyl* (pentyl)
anilino (phenylamino)
anisidino
anthranoyl (2-aminobenzoyl)
arsino
azelaoyl (from azelaic acid)
azido
azino
azo
azoxy
benzal* (benzylidene)
benzamido (benzoylamino)
benzhydryl (diphenylmethyl)
benzoxy* (benzoyloxy)
benzoyl
benzyl
benzylidene
benzylidyne
biphenylyl
biphenylene
butoxy
sec-butoxy (1-methylpropoxy)
tert-butoxy (1,1-dimethylethoxy)
butyl
sec-butyl (1-methylpropyl)
tert-butyl (1,1-dimethylethyl)
butyryl (1-oxobutyl)
caproyl* (hexanoyl)
capryl* (decanoyl)
capryloyl* (octanoyl)
carbamido (carbamoylamino)
carbamoyl (aminocarbonyl)
carbamyl (aminocarbonyl)
carbazoyl (hydrazinocarbonyl)
carbethoxy (ethoxycarbonyl)
carbonyl
carboxy
cetyl* (hexadecyl)
chloroformyl (chlorcarbonyl)
CH3CONHCH3COCH2COCH3COCH2CH3COCH2=CHCOCH3CH(NH2)COH2N(CH2)2COCH2=CHCH2CH2=CHCH=
H2NC(=NH)H2NCH3(CH2)4C6H5NHCH3OC6H4NH2-H2NC6H4COAsH2-OC(CH2)7CON3=N-N=
-N=N-N(O)=NC6H5CH=
C6H5CONH(C6H5)2CHC6H5COOC6H5COC6H5CH2C6H5CH=
C6H5C=
C6H5C6H5-C6H4-C6H4C4H9OC2H5CH(CH3)O(CH3)3COCH3(CH2)3CH3CH2CH(CH3)(CH3)3CCH3(CH2)2COCH3(CH2)4COCH3(CH2)8COCH3(CH2)6COH2NCONHH2NCOH2NCOH2NNHCOC2H5OCO=C=O
HOOCCH3(CH2)15ClCO-
cinnamoyl
cinnamyl (3-phenyl-2-propenyl)
cinnamylidene
cresyl* (hydroxymethylphenyl)
crotonoyl
crotyl (2-butenyl)
cyanamido (cyanoamino)
cyanato
cyano
decanedioyl
decanoyl
diazo
diazoamino
disilanyl
disiloxanyloxy
disulfinyl
dithio
enanthoyl* (heptanoyl)
epoxy
ethenyl (vinyl)
ethynyl
ethoxy
ethyl
ethylene
ethylidene
ethylthio
formamido (formylamino)
formyl
furmaroyl (from fumaric acid)
furfuryl (2-furanylmethyl)
furfurylidene (2-furanylmethylene)
glutamoyl (from glutamic acid)
glutaryl (from glutaric acid)
glycylamino
glycoloyl; glycolyl (hydroxyacetyl)
glycyl (aminoacetyl)
glyoxyloyl; glyoxylyl (oxoacetyl)
guanidino
guanyl (aminoiminomethyl)
heptadecanoyl
heptanamido
heptanedioyl
heptanoyl
hexadecanoyl
hexamethylene (1,6-hexanediyl)
hexanedioyl
hippuryl (N-benzoylglycyl)
hydrazino
hydrazo
hydrocinnamoyl
C6H5CH=CHCOC6H5CH=CHCH2C6H5CH=CHCH=
HO(CH3)C6H4CH3CH=CHCOCH3CH=CHCH2NCNHNCONC-OC(CH2)8COCH3(CH2)8CON2=
-NHN=NH3SiSiH2H3SiOSiH2O-S(O)S(O)-SSCH3(CH2)5CO-OCH2=CHHCCC2H5OCH3CH2-CH2CH2CH3CH=
C2H5SHCONHHCO-OCCH=CHCOOC4H3CH2OC4H3CH=
-OC(CH2)2CH(NH2)CO-OC(CH2)3COH2NCH2CONHHOCH2COH2NCH2COHCOCOH2NC(=NH)NHH2NC(=NH)CH3(CH2)15COCH3(CH2)5CONH-OC(CH2)5COCH3(CH2)5COCH3(CH2)14CO-(CH2)6-OC(CH2)4COC6H5CONHCH2COH2NNH-HNNHC6H5(CH2)2CO-
2-16
HC&P_S02.indb 16
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HC&P_S02.indb 17
HOOHONHHOHN=
OIO2I(CH3)2CH(CH2)2(CH3)2C=CH(CH3)2CHCH2O(CH3)2CHCH2(CH3)2CHCH=
(CH3)2CHCOOCNCN(CH3)2CH(CH2)3C2H5CH(CH3)CH(NH2)COHON=
(CH3)2CH(CH2)2(CH3)2CHCH2CH=
CH2=C(CH3)(CH3)2CHO(CH3)2CH(CH3)2C=
SCN(CH3)2CHCH2COCH3CH(OH)COCH3(CH2)10COCH3(CH2)11(CH3)2CHCH2CH(NH2)COCH3CO(CH2)2CO-OCCH2COC6H5CH(OH)COHS2,4,6-(CH3)3C6H2CH2=C(CH3)COCH2=C(CH3)CH2CH3SCH2CH2CH(NH2)COCH3OH3CH2C=
CH3SCH3(CH2)12COCH3(CH2)13(C10H7)-(C10H6)(CH3)3CCH2O2NNHO2NONNHONN=
ONCH3(CH2)7COCH3(CH2)7CH=CH(CH2)7CO-OCCOO=
CH3(CH2)14CO-(CH2)5CH3(CH2)4CH3CH2C(CH3)2C6H5COCH2C6H5COCH=
C6H5CH2CH2C6H5OC6H5-
2-17
phenylene (benzenediyl)
phosphino* (phosphanyl)
phosphinyl* (phosphinoyl)
phospho
phosphono
phthaloyl (from phthalic acid)
picryl (2,4,6-trinitrophenyl)
pimeloyl (from pimelic acid)
piperidino (1-piperidinyl)
pivaloyl (from pivalic acid)
prenyl (3-methyl-2-butenyl)
propargyl (2-propynyl)
1-propenyl
2-propenyl (allyl)
propionyl* (propanyl)
propoxy
propyl
propylidene
pyrryl (pyrrolyl)
salicyloyl (2-hydroxybenzoyl)
selenyl* (selanyl; hydroseleno)
seryl (from serine)
siloxy
silyl
silylene
sorboyl (from sorbic acid)
stearoyl (from stearic acid)
stearyl (octadecyl)
styryl (2-phenylethenyl)
suberoyl (from suberic acid)
succinyl (from succinic acid)
sulfamino (sulfoamino)
sulfamoyl (sulfamyl)
sulfanilyl [(4-aminophenyl)sulfonyl]
sulfeno
sulfhydryl (mercapto)
sulfinyl
sulfo
sulfonyl (sulfuryl)
terephthaloyl
tetramethylene
thienyl (from thiophene)
thiocarbonyl (carbothionyl)
thiocarboxy
thiocyanato (thiocyano)
thionyl* (sulfinyl)
threonyl (from threonine)
toluidino [(methylphenyl)amino]
toluoyl (methylbenzoyl)
tolyl (methylphenyl)
-tolyl (benzyl)
tolylene (methylphenylene)
tosyl [(4-methylphenyl) sulfonyl)]
triazano
trimethylene (1,3-propanediyl)
trityl (triphenylmethyl)
valeryl* (pentanoyl)
valyl (from valine)
vinyl (ethenyl)
vinylidene (ethenylidene)
xylidino [(dimethylphenyl)amino]
xylyl (dimethylphenyl)
xylylene [phenelenebis(methylene)]
-C6H4H2PH2P(O)O2P(HO)2P(O)1,2-C6H4(CO-)2
2,4,6-(NO2)3C6H2-OC(CH2)5COC5H10N(CH3)3CCO(CH3)2C=CHCH2HCCCH2-CH=CHCH2
CH2=CHCH2CH3CH2COCH3CH2CH2OCH3CH2CH2CH3CH2CH=
C3H4N2-HOC6H4COHSeHOCH2CH(NH2)COH3SiOH3SiH2Si=
CH3CH=CHCH=CHCOCH3(CH2)14COCH3(CH2)17C6H5CH=CH-OC(CH2)6CO-OCCH2CH2COHOSO2NHH2NSO24-H2NC6H4SO2HOSHSOS=
HO3S-SO21,4-C6H4(CO-)2
-(CH2)4(C4H3S)=CS
HOSCNCS-SOCH3CH(OH)CH(NH2)COCH3C6H4NHCH3C6H4COCH3C6H4C6H5CH2-(CH3C6H3)4-CH3C6H4SO2H2NNHNH-(CH2)3(C6H5)3CCH3(CH2)3CO(CH3)2CHCH(NH2)COCH2=CHCH2=C=
(CH3)2C6H3NH(CH3)2C6H3-CH2C6H4CH2-
5/2/05 2:50:39 PM
2-18
1
3 2
Cyclopropane
N
1
5
4
1
2
1
4
5
4
Cyclobutane
Spiropentane
H
N
2
3
2
3
H
N
5
4
5 1 2
4
3
5 1 2
4
3
5 1 2
4
3
Furan
Thiophene
Pyrrole
(Azole)
2
3
Cyclopentane
H
N
5 1 2S
4
3
H
N
2
3
3H-Pyrrole
(3H-Azole)
Pyrazole
(1,2-Diazole)
5 1 2
4
3
5 1 2N
4
3
2H-Pyrrole
(2H-Azole)
5 1 2N
4
3
5 1 2S
4
3
5 1 2
4
3
N
1
5 1 2
4
3
5 1 2
4
3
5 1 2N
5 1 2N
N
N
N
S
4
3
4
3
2H-Imidazole
Isoxazole
Thiazole
Oxazole
N
N
(1,3-Diazole) 1,2,3-Triazole 1,2,4-Triazole 1,2-Dithiole 1,3-Dithiole 3H-1,2-Oxathiole (1,2-Oxazole) (1,3-Thiazole) (1,3-Oxazole)
5 1 2N
4
3
5 1 2N
4
3
5 1 2N
4
3
N
1,2,3-Oxadiazole
Isothiazole
(1,2-Thiazole)
N
1,2,4-Oxadiazole
5 1 2O
4
3
5 1 2O
4
3
N5
1 2N
4
3
5 1 2N
4
3
5 1 2
4
3
1,2,5-Oxadiazole
(Furazan)
N
N
1,3,4-Oxadiazole
5 1 2N
4
3
5 1 2
4
3
N5
1 2S
3
1 2N
3
N
1,2,3,5-Oxatriazole
6
5
5 1 2
4
3
N
N
1,2,3,4-Oxatriazole
N5
6
5
2
3
2
3
N
O
N
O
S
H
1,2,4-Dioxazole 1,3,2-Dioxazole 1,3,4-Dioxazole 5H-1,2,5-Oxathiazole 1,3-Oxathiole Benzene Cyclohexane
3H-1,2,3-Dioxazole
O
6 1 2
5
3
4
2H-Pyran
4H-Pyran
6
5
H
N
1
6 1 2
5
3
4
2H-Pyran-2-one
(2-Pyrone)
6 1 2
5
3
N 4 N
2
3
6 1 2
5
3
4
6
5
N
1
6 1 2
5
3
4
6 1 2O
5
3
4
6 1 2
5
3
4 O
O
4H-Pyran-4-one
(4-Pyrone)
1,2-Dioxin
1,3-Dioxin
2N
3
6
5
N
1
2N
3
6
5
N
1
4
6
5
N
1
4
2N
3
6
5
Pyridazine
Pyridine
6 1 2N
5
3
4
2
3
N
1
6
5
2
3
2
3
N
Pyrazine
Pyrimidine
6 1 2N
5
3
4
6 1 2
5
3
4 N
6 1 2
5
3
4 N
N
1
6 1 2
5
3
4
4
4 N
N
N
1,3,5-Triazine 1,2,4-Triazine 1,2,3-Triazine 4H-1,2-Oxazine 2H-1,3-Oxazine 6H-1,3-Oxazine 6H-1,2-Oxazine 1,4-Oxazine
(s-Triazine)
(as-Triazine) (v-Triazine)
Piperazine
4
N
H
6 1 2N
5
3
4
6 1 2S
N5 4 3
6 1 2
5
3
4
N6
5
6 1 2N
5
3
4
1 2S
3
4
H
N
6 1 2
N5 4 3N
7 1 2
6 1 2
5
3
4
5 4
N
N
N
1,2,5-Oxathiazine 1,2,6-Oxathiazine 1,2,4-Oxadiazine 1,3,5-Oxadiazine Morpholine Azepine
2H-1,2-Oxazine
H
4H-1,4-Oxazine
7 1 2
6
3
5
7 1 2
6
Oxepin
6
5
7
4
3
5
1 2S
3
N
1
5
6
5
2N
3
4
6
5
7
4
H
N
1 2
3
Indole
6
5
7
4
1 2
3
3H-Indole
2
3
6
5
7
4
6
5
1 2
3
7
4
6
5
2H-Indene
(Isoindene)
Indene
4H-1,2-Diazepine
Thiepin
Benzo[c]thiophene
HC&P_S02.indb 18
7
6
2N
3
1H-Indole
3
2
4
1
7
4
1 2
3
Benzofuran
6
7
N
Cyclopenta[b]pyridine
O6
5
7
4
6
5
7
4
1 2O
3
6
5
Isobenzofuran
N
1
2
3
Pyrano[3,4-b]pyrrole
6
5
7
4
1 2
3
Benzo[b]thiophene
H
N
1 2N
3
Indazole
6
5
7
4
1 2N
3
Benzisoxazole
(Indoxazene)
5/2/05 2:51:05 PM
6
5
1 2
3
6
5
N
1
7
4
2O
3
7
6
2
3
7
6
2-19
2
3
7
6
1
4
2
3
7
6
1 2
3
4
7
6
1 2
3
4
O
7
6
1 2
3
4
7
6
O
4H-1-Benzopyran-4-one
(Chromen-4-one)
N
7
6
1,8-Naphthyridine
7
6
2O
3
1 2
3
4
2O
3
7
6
1H-2,3-Benzoxazine
7
6
1 2
3
4
1,7-Naphthyridine
7
6
7
6
4H-3,1-Benzoxazine
1 2N
3
4
8
5
1 2
3
4
7
6
1 2
3
4
H
7
6
7
6
2N
3
1
9
8
7
6
4
5
1
4
Fluorene
2
3
7
6
2
3
7
6
10
Carbazole
Xanthene
2
3
6
7
5
8
3
2
Acridine
1 2
3
4 N
1 2
3
4
2H-1,4-Benzoxazine
10
2
3
Anthracene
10
Quinazoline
7
6
4H-1,4-Benzoxazine
H
N
9
7
6
Cinnoline
1 2
3
4 N
7
6
N
H
2H-1,2-Benzoxazine
2H-1,3-Benzoxazine
1 2
3
4
7
6
2N
3
Isoquinoline
Quinoline
1,6-Naphthyridine
1,5-Naphthyridine
2O
3
7
6
O
3H-2-Benzopyran-1-one
(Isochromen-3-one)
2O
4 3
7
6
1H-2-Benzopyran-1-one
(Isocoumarin)
N7
1 2
3
4
6
7
3 2
1
5
8
10
Phenanthrene
2 1
3
4 76
5
Norpinane
(Bicyclo[3.1.1]heptane)
N1
6
3
H
N
5
4
7 8
9
7H-Purine
Phenalene
R'
R
2
3
1
4
H 11 12 13
10
5
14
R''
17
16
15
8
H
6 7H
HC&P_S02.indb 19
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