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ORGANIC SUBSTITUENT GROUPS AND RING SYSTEMS

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

by systematic rules (e.g., methyl from methane, ethyl from ethane,


etc.) are included here only for the first few members of a homologous series.
In the second part of the table a number of common organic
ring compounds are shown, with the conventional numbering of
the ring positions indicated.
The help of Warren H. Powell in preparing this table is greatly appreciated. Pertinent references may be found in the table
Nomenclature of Chemical Compounds.

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-

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Organic Substituent Groups and Ring Systems


hydroperoxy
hydroxyamino
hydroxy
imino
iodoso* (iodosyl)
iodyl
isoamyl* (isopentyl; 3-methylbutyl)
isobutenyl (2-methyl-1-propenyl)
isobutoxy (2-methylpropoxy)
isobutyl (2-methylpropyl)
isobutylidene (3-methylpropylidene)
isobutyryl (2-methyl-1-oxopropyl)
isocyanato
isocyano
isohexyl (4-methylpentyl)
isoleucyl (from isoleucine)
isonitroso* (hydroxyamino)
isopentyl (3-methylbutyl)
isopentylidene (3-methylbutylidene)
isopropenyl (1-methylethenyl)
isopropoxy (1-methylethoxy)
isopropyl (1-methylethyl)
isopropylidene (1-methylethylidene)
isothiocyanato (isothiocyano)
isovaleryl* (3-methyl-1-oxobutyl)
lactoyl (from lactic acid)
lauroyl (from lauric acid)
lauryl (dodecyl)
leucyl (from leucine)
levulinoyl (from levulinic acid)
malonyl (from malonic acid)
mandeloyl (from mandelic acid)
mercapto
mesityl
methacryloyl (from methacrylic acid)
methallyl (2-methyl-2-propenyl)
methionyl (from methionine)
methoxy
methyl
methylene
methylthio
myristoyl (from myristic acid)
myristyl (tetradecyl)
naphthyl
naphthylene
neopentyl (2,2-dimethylpropyl)
nitramino (nitroamino)
nitro
nitrosamino (nitrosoamino)
nitrosimino (nitrosoimino)
nitroso
nonanoyl (from nonanoic acid)
oleoyl (from oleic acid)
oxalyl (from oxalic acid)
oxo
palmitoyl (from palmitic acid)
pentamethylene (1,5-pentanediyl)
pentyl
tert-pentyl
phenacyl
phenacylidene
phenethyl (2-phenylethyl)
phenoxy
phenyl

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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-

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Organic Substituent Groups and Ring Systems

2-18

Organic Ring Compounds


5
4

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

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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)

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Organic Substituent Groups and Ring Systems

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

Octahydronaphthalene 2H-1-Benzopyran 2H-1-Benzopyran-2-one


1,2,3,4-Tetra(Decalin)
hydronaphthalene
(2H-Chromene)
(Coumarin)
(Tetralin)

Benzoxazole 2,1-Benzisoxazole Naphthalene

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

R = Nearly always methyl


R' = Usually methyl
R'' = Various groups

Steroid ring system

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