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)
cinnamoyl
cinnamyl (3-phenyl-2-propenyl)
cinnamylidene
cresyl* (hydroxymethylphenyl)
crotonoyl
crotyl (2-butenyl)

2000 by CRC PRESS LLC

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)15ClCOC6H5CH=CHCOC6H5CH=CHCH2C6H5CH=CHCH=
HO(CH3)C6H4CH3CH=CHCOCH3CH=CHCH2-

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
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)

NCNHNCONC-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)2COHOOHONHHOHN=
OIO2I(CH3)2CH(CH2)2(CH3)2C=CH(CH3)2CHCH2O(CH3)2CHCH2(CH3)2CHCH=
(CH3)2CHCO-

ORGANIC SUBSTITUENT GROUPS AND RING SYSTEMS (continued)

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
phenylene (benzenediyl)
phosphino* (phosphanyl)
phosphinyl* (phosphinoyl)
phospho
phosphono
phthaloyl (from phthalic acid)

2000 by CRC PRESS LLC

OCNCN(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-C6H4H2PH2P(O)O2P(HO)2P(O)1,2-C6H4(CO-)2

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)]

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-

ORGANIC SUBSTITUENT GROUPS AND RING SYSTEMS (continued)

ORGANIC RING COMPOUNDS
H
5

1
3

Spiropentane

Cyclopropane

5
4

Cyclobutane

2
3

N
5
4

5
4

2
3

Pyrazole
(1,2-Diazole)

N
2H-Imidazole
(1,3-Diazole)

N
1,2,3-Triazole

N
1,2,4-Triazole

1,2-Dithiole

5
4

Thiazole
(1,3-Thiazole)
O
1
5
2O
3

1,2,3,5-Oxatriazole

2
3

Oxazole
(1,3-Oxazole)
O
N 5 1 2N

1,2,3,4-Oxatriazole

2
3

Isoxazole
(1,2-Oxazole)
O
1
5
2N
N

3H-1,2,3-Dioxazole

2
3

2
3

Isothiazole
(1,2-Thiazole)
O
1
5
2O
H

2
3

2N

1,3,2-Dioxazole

2
3

2H-Pyrrole
(2H-Azole)

O
2

2S
3

4
S
1,3-Dithiole

3H-1,2-Oxathiole

N5

2N

N
2

N
N
N
N
1,2,3-Oxadiazole 1,2,4-Oxadiazole 1,2,5-Oxadiazole 1,3,4-Oxadiazole
(Furazan)
O
O
O
O
1
1
1
H N 5 1 2S
5
2N H
5
2
5
2

1,2,4-Dioxazole

O
6

2N

5
4

3H-Pyrrole
(3H-Azole)
1

S
2S
3

Pyrrole
(Azole)

2
3

Thiophene

1
2
3

H
1
5
4

Furan

N
N

Cyclopentane

O
2

1,3,4-Dioxazole

5H-1,2,5-Oxathiazole

O
2

O
2

1,3-Oxathiole

O
2O

2
3

Benzene

Cyclohexane

2H-Pyran

4H-Pyran

2H-Pyran-2-one
(2-Pyrone)

O
4H-Pyran-4-one
(4-Pyrone)

1,2-Dioxin

1,3-Dioxin

H
N

6
5

6
5

3
4

2N

6
5

3
4

2
3

6
5

N
6

N
3

Pyridazine

Pyrimidine

Pyrazine

H
Piperazine

2N

6
5

2
3

6
5

2
3

6
5

6
5

3
4

6
5

N
1

2
3

6
5

1
6
5

2H-1,3-Oxazine 6H-1,3-Oxazine
O
O
1
1
N
H
2
6
2
6
5

3
4

1,4-Oxazine

H
4H-1,4-Oxazine

2H-1,2-Oxazine

6
5

1,2,3-Triazine
(v-Triazine)
O
1
S

2H-1,2-Oxazine
O
1
2N
6
5

3
4

1,2,5-Oxathiazine

6
5

3
4

6
5

2N

6
5

3
4

1,4-Oxazine
O
1
N
2S

1,3,5-Triazine
1,2,4-Triazine
(s-Triazine)
(as-Triazine)
O
O
1
1
N H

6H-1,2-Oxazine
O
1
6
2S

1
6
5

N
4H-1,2-Oxazine
O

N
2N

Pyridine

H
4H-1,4-Oxazine 1,2,5-Oxathiazine
O
O
1

6
5

3
4

6
5

2
3

1,2,6-Oxathiazine 1,2,4-Oxadiazine 1,3,5-Oxadiazine

Morpholine

H
N

3
5

Azepine

2000 by CRC PRESS LLC

3
5

Oxepin

3
5

Thiepin

3
5

4H-1,2-Diazepine

7
6
5

Indene

O
2
3

6
5

2H-Indene
(Isoindene)

2
3

6
5

Benzofuran

2
3

6
5

2O
3

Isobenzofuran

ORGANIC SUBSTITUENT GROUPS AND RING SYSTEMS (continued)

ORGANIC RING COMPOUNDS (continued)
H
S
6
5

1 2

6
5

Benzo[b]thiophene

1 2S
3

7
4

6
5

N
2
3

Benzo[c]thiophene

6
5

N
2
3

2N
3

3
2

3H-Indole

Indole

6
5

6
7

N
Cyclopenta[b]pyridine

1H-Indole

H
N
6
5

1 2N

6
5

Indazole

1 2N

Benzisoxazole
(Indoxazine)

Benzoxazole

1 2O
3

6
5

7
6

2,1-Benzisoxazole

2
3

7
6

Naphthalene

O
8
5

1
2
3

7
6

2H-1-Benzopyran
(2H-Chromene)
8
5

2
3

7
6

7
6

2O

7
6

2O
3

7
6

2H-1-Benzopyran-2-one 4H-1-Benzopyran-4-one 1H-2-Benzopyran-1-one 3H-2-Benzopyran-1-one

(Coumarin)
(Chromen-4-one)
(Isocoumarin)
(Isochromen-3-one)

N
7
6

N
N

2
3

7
6

2
3

7
6

N
N

2
3

7
6

2
3

Pyrano[3,4-b]pyrrole

7
6

2
3

7
6

7
6

2N
3

Isoquinoline

N
2
3

Octahydronaphthalene
(Decalin)

Quinoline

N
2
3

1,2,3,4-Tetrahydronaphthalene
(Tetralin)
N

O
7
6

6
5

1 2

6
5

O
2
3

7
6

2
3

N
Cinnoline

Quinazoline

1,8-Naphtyridine

1,7-Naphtyridine

1,5-Naphtyridine

O
7
6

1,6-Naphtyridine

O
2
3

7
6

2
3

6
7

3
2

7
6

1H-2,3-Benzoxazine

7
6

4 3

4H-3,1-Benzoxazine

3 2

N H

2
3

2H-1,4-Benzoxazine

N
H

2H-1,2-Benzoxazine

4H-1,4-Benzoxazine

1
7
6

6
7

2
3

10

Anthracene

5
8

9
8

10

Phenanthrene

7
6

6 5

1
2
3

Phenalene

Fluorene

H
N

N
7
6

1
2
3

7
6

8
5

5
2
3

10

6
7

10

O
Carbazole

Xanthene

Acridine
R

4
1

3
2

3
4

2 1
5

N
N

1
2

6
3

N
7H-Purine

2000 by CRC PRESS LLC

14
8 H H
7

10

2
3
4

17

16
15

1
8
9

11

12 13

Steroid ring system

7 6

Norpinane
(Bicyclo[3.1.1]heptane)

R = Nearly always methyl

R = Usually methyl
R = Various groups

2H-1,3-Benzoxazine