Key Functional Groups

R may be any unspecified group including H. Where two or more R groups are indicated these may be the same or different groups. Where aromatic rings or other cyclic systems are shown they may also contain substituents when they are not specified as part of the key functional group.

Acetal

Alicyclic ketone

(CH2) C=O

Acetamide

CH3CNHR

Alkadiene

C=CH-CH=~ /

N-Acetoxy

N-Acetyl aryl amine

iso-Alkane

RCH2, RCH2

CH-

Acetylene

RCfCR

Alkene

/ \C=C<

N-Acetylimine

R,

Alkene carboxamide

RCH=CHCONHR

R/C=N-CCH3

Acetyl t hio

Alkene carboxylate

RCH=CHC02R

Adenine

);

L,

Alkene carboxylic acid

H

RCH=CHC02H

Alanine

H2NCH(CH3)C02H

Alkenyl aldehyde

RCH=CHCHO

tert-Alcohol

R
R~C-OH

Alkenyl ketone

0
RCH=CHCR
ll

ix

Alkyl alcohol

RCH20H

iso-Alkyl aryl amine

sec-Alkyl alcohol

R CH-OH R

sec-Alkyl aryl amine

tert-Alkyl alcohol

R\ RC ,

-OH

Alkyl aryl ether

RCH20

Alkyl aldehyde

RCHpCHO

Alkyl aryl sulfoxide

R C H 2 ! a

Alkyl amide

RCNHCH2 R

: :

Alkyl aryl thioether

R C H 2 S a

Alkyl amine

RCH2NH2

Alkyl azoxy

Alkyl tert-amine

N-R

Alkyl carbamate

0 It RCH2OCNHR

sec-Alkyl amine

ZCH-NHR R
R R-\C-NHR R

Alkyl carbonate

KH20,

RCH,O

c=o

tert-Alkyl amine

Alkyl carboxamide

RCH2CNHR

Alkylamino

RCHZNH-

iso-Alkyl carboxamide

RCHCNHR ?
R

iso-Alkylamino/iso-alkylamine

R\ R~cHNH-

Alkyl carboxylate

RCH2C02R

*CN *-

Alkyl aryl amide

0
X

/CH2R

tert-Alkyl carboxylate

R~C--CO,R
R

Alkyl carboxylic acid

RCH2COH

i:

N -Alkylimine

R-CHzN-R

iso-Alkyl carboxylic acid

o \CH;OH R

N-Alkylindole

QQ
R

0 II RCH2CR

Alkylcyclohexane

N-Alkylmorpholine

Alkyl cyclopentane

RCH2-()

Alkyl nitrate

RCHzON02

Alkyl ester

RCOCH2R
0

Alkyl nitrile

R&N CC

iso-Alkyl ester

Alkyl N-oxide

Alkyl ether

RCH2OR

Alkyl peroxide

RCHpO-OCHpR

Alkyl hydrazide

RCNHNHR

!?

Alkylphenyl

Alkyl hydrazine

RCHzNHNHR

iso-Alkyl phenyl
R

N -Alkylimidazole

CH2R

Alkyl phosphate

RCH20P OR
OR

: :

Alkyl imide

Alkyl phosphine

G P-R
R

N-Alkyl imide

N-Alkylpiperazine

RNVNCH2

xi

N-Alkylpiperidine
NHR
I

S-Alkyl thiocarbamate

RCH@ONHR

N-Alky lpurine
ri

Alkyl thiocarboxylate

RCH2C,/

/o
SR

Alkylpyridine

Alkyl thioester

RCSCH2R

Alkylpyridone

Alkyl thioe ther

RCH2SR

N -Alkylpyridone

Alkyl thiol

RH H C&
0 I1

Alkylpyrimidine

N+

LNTCHpR

Alkylurea

RNHCNHCH2R

N -Alky1pyrrolidine

(2
R

Alkyne

RCECR

Alkyl quaternary ammonium

\+ -N-CH,R /

Allyl

Alkyl sulfamate

RCHpOSOpNHR

Allyl amine

Alkyl sulfate

RCHpOSOaH

Allylic alcohol

RCH=CHCHOH

F;1

Alkyl sulfonate

RCHpOSOpR

Allylic methyl

CH&H=CHR

Alkyl sulfonic acid

RCH&OaH

Amidine

RC' +NR

NR,

Alkyl sulfoxide

RCHpS,

f0
R

Amidoxime

xii

Amino acid Aminoglycoside

RCHNH2 CO2H
I

Ant hr acene

Anthraquinone

@
0
eCH2CONH2 e C H 2 C O Z H

Aminoimidazole
H H

Aminoimidazoline

Aryl acetamide

Aryl acetic acid Aminopurine Aryl aldehyde Aminopyridine Arylalkene Aminoquinoline Arylalkyl Aminothiazole Aryl tert-alkyl Aminothiophene Aryl amide Aminot riazine Aryl amine

Androstadienone

Aryl amino acid

Aryl carbamate

Androsten-3-one
Aryl carboxamide

Xlll

...

Aryl carboxylate

@OR

Aryl ketone

Aryl carboxylic acid

-H ! O

Arylmethyl

Aryl dihydrodiol

a: :

Aryl methyl ketone

Aryl disulfide

Aryl nitrile

Aryl ester

N-Arylnitrosamine

Aryl ether

Arylnitroso

Aryle t hylene

o C H z C H 2

Aryl N-oxide

Aryl hydrazine

O N H N H 2

Aryloxacetic acid

Arylhydroxylamine

O N H o H

Aryloxypropionic acid

Arylhydroxymethy1

( & X - l * O H

Aryl phosphate

N-Arylimide

Arylpiperidine

N-Arylimine

N
NCO

Aryl propionic acid

Aryl isocyanate

Aryl sulfonic acid

xiv

Aryl thiocarboxymide

Q-LHR

Benzazepine

Aryl t hiocarboxylate

O ! O R

Benzhydrol

Aryl thioether

Benzhydryl

76H5

Aryl thiol

Benzhydryl carboxylate

RCO~-CR
I
c6H5

Aryl triazene

Azetidine

Benzimidazole

hide

R-N=N=N

+ -

Benzimidazoline

Aziridine

7 4

Benzodiazepine

Azobenzene

Benzodioxane

R-N=N-R

AzoxY

Benzodioxin

Barbiturate

:2xo
0
R

Benzofuran

Benzamide

Benzofurazan

a:N;o N

Benzan t hr acene

&

Benzoindoline

Benzoisoselenazolone

R :@

Benzotriazine

Benzoisothiazole

Benzotriazole
R

Benzoisoxazole
CN

1,2-Benzoxazole

Benzonitrile

Benzo(c1phenanthrene

Benzoxazoline

Benzopyran

Benzyl

Benzopyranone

cjo

Benzyl alcohol

Benzyl amine Benzo[a]pyrene

Benzoquinone

6
0

Benzyl bromide

Benzyl ester

Benzothiadiazole

Benzyl ether

Benzothiazine

us] aR
Y
R
XVl

Benzyl nitrile

0 C H 2 C *

Benzothiazole

N-Benzylpiperidine

OCH*(-J

Benzyl thioether

e C H 2 S R

Chiral carbon

Biphenyl

Q-Q
! BrCH2CR
BrCH2R

Chloroacetamide

CICH2CNHR

!
II

Bromoacetyl

Chloroacetyl

CKH2CR

Bromoalkane

Chloroalkane

CICH2R

Bromoalkyl

Bat!

Chloroalkene

CICH=CHR

Bromophenyl

Chloroalkyne

CICECR

Bromopyridine

Chloroalkyl

,R CICH,

iso-Butyl

Chlorobenzoyl
CH3 CH3-kCH3'

tert-Butyl

Chlorobenzyl

N-ter t -Butyl

'N-c(cH,)~

R'

Chlorobiphenyl

Carbamate

ROCNHR

Chlorocyclopropane

&Cl

Carbazole

N-Chloroethyl

CICH,CH,N<

Cephalosporin

RNHn>R
0

Chlor opheny1

CI

k02H

Ch 1oropyr idazinone

'C I

k , R

Cycloalkene

l $ &

Chloropyridine

Cycloalkylamine

Chlorotriazine

N'

R kNJ
N

Cycloalkyl amine

(CH2)n

n
W

CH-NH2

Cycloalkyl ester Chlorour acil

H
OAN

(CHd,

n:: CHOCR
W

Cyclohexadienone

Cholanic acid

Cyclohexane/cyclohexyl

CtFC0*"
Cholestenone
HO

Cyclohexanol

6
O * H

Cyclohexanone

i i
0

Chrysene

Cyclohexene

Coumarin

Cyclohexenol

Cyanamide

RNHCN

Cyclohexenone

oo
c>N&

N-Cyanoguanidine

RNHENHR
NCN

Cyclohexyl amide

Cycloalkane/cycloalkyl

Cyclopentene

xviii

Cyclopentenone

Do
B!!
D-CH2R

Dialkyl aryl amine

Cyclopropane

Dialkyl ether

RCH2OCH2R

Cyclopropylalkyl

Dialkylisoxazole

Cyclopropyl carboxylate

p, .
R-NCH24

Dialkyl sulfonamide

W02kR R ,

N-Cyclopropylmethyl

Dialkyl sulfone

RSOpR

Cysteine

H02CCHCH2SH
I
NH2

Dialkyl sulfoxide

RCH2SCH2R

Cyt i dine

Dialkyl thioether

RCH2SCH2R

OH OH

Diaryl amine

Q-.G
/ \
/ \

Cytosine
H

Diaryl ether

Dialkyl amide

Diaryl sulfoxide

@ a
0

/ \

/ \

Dialkyl amine

Diaryl t hioet her

0a / \
/ \

9
Dialkylamino Diazepine

Diazohydroxide

RN=N-OH

XiX

Dibenzazepine

Dihydrofuran

Dibenzocycloheptane

Dihy dropyr an

Dibenzocycloheptene

Dihydropyridazinone

Dibenzofuran

Dihydropyridine

0
R

Dibenzothiazine

Dihydroquinoline

Dibenzothiepine

Dihydrothiazine

Dibenzoxepine

Dimethylamide

RCN\

: :

9 4 3

CH3

Dichloroalkene

H::
F2CH-R

> ( I =

Dimethylamino

H3C, H3C

N-R

Difluoromethyl

Dimethylaminoalkyl

H3C, H3C

NCHZR

Digitoxigenin

Dimethylcarbamate

0 H3C. NCOR It
H3C

Dihydroarene

0
02

Dimethylcyclopropyl

H3xH3
H3C, H3C NSOZR

Dihydrobenzofuran

Dimet hylsulfonamide

Dihydrodiol

Dioxolane

Diphenyl ether

Fluoroalkyl

FCH2CH:
R

Disulfide

R-S-S-R

Fluorocytosine
S II

Dithiocarbamate

RCH2NHCSR

tH2OH

Fluor ohexose Dithiolane

Epoxide

Ester glucuronide

* qR
HO,C

0 s-s

Fluromethoxyphenyl

0 0 C t - 1 2 F or --OCHF2

Fluor ophenyl

HO

b
HN%F
OJ-N

Ethynyl

R-C=C-R

Fluor our acil

Fatty acid (saturated)

R(CH2),CO2H

Formamide

RNHCHO

Fatty acid (unsaturated)

R(CH=CH),CH2CO,H

N -For my1

(R)*NCHO

Fluoranthene

Furan

Fluorene

Furfural

QCHO

Fluoroacetyl

FCH2C-R

Furoyl carboxylate
R

QCOR II 0

Fluoroalkene

CHZCH:
R

Germanorganic

Glutamic acid

C02H I HZNCHCH2CH2COzH

Hydroperoxide

ROOH OH
I

Glutathione

HO2C$HCH2CH2CO-NHCHCO-NHCH2C02H NH2 CHZSH I

Hydroquinone
OH

Glycolamide

RCHCONHR

YH

Hydroxamic acid

RCYOH

II

Glycoside

O
HO

R OH

N-Hydroxy

R 'N-OH
R'

Guanidine

RNHCNHp

tH

N-Hydroxy aryl amide

0

Haloalkyne

(Br)CICZCR

Hydroxycoumarin

Hexahydroazepine

0
0

Hy droxyisoxazole

Hexahydronaph t halene

Hy droxylamine

RNHOH

Hexose

Hydroxypiperidine

R--NT\ L'O"

Hydantoin

? o J
0

N-Hydroxy sulfate
H

R
'N-OSO,H R'

Hydrazide

dkNHNH2

N-Hydroxyurea

RN-ENHz

PH

Hydrazine

RNHNHz

Imidazole
H

Hydrazone

RCH=NNHR

Imidazolidinone
0

xxii

Imidazoline
H

Ketal

Imidazopyridine

Lactam

Iminecarboxylate

II =N-C-OR

Lactone

Indane

Leucine

Indene

Lysine

Indole

Macrocyclic lactone

Indolone

Mercapturic acid

NHCOCH3 RSCH&HCO,H I

Iodoalkyl

ICH2R

Methanesulfonamide

RNHS02CH3

Iodophenyl

Methanesulfonate

CH3S020R

OH

Isoprenoid

o-Me t hoxyphenol

Isoquinoline

Met hoxypheny1

Isothiocyanate

RN=C=S

Methoxypyridine

Isoxazole

fi
0-N

N-Methylalkylamine

R.

N-CH,

R'

xxiii

Methyl arnide

0 II RCNHCH3

Methylcyclohexenone

N-methy lamidine

NH II R-CNHCH3

N-Methyl diary1 arnine

Met hylamino

CH3NHR

N-Methyldiazepine

NwNCH3

fi

N-Methyl aryl amine

e N H C H 3

N-Met hylperhydrodiazepine

YJNCH3
RCOCH3

N-Methylaziridine

Methyl ester

N-Methy1azepine
CH3

Methyl ether

CH30R

N-Methylbenzylamine

e C H 2 N H C H 3

N-Met hylhexahydroazepine

C N C H 3

Methyl carbamate

RNHCOCHs

N-Methylimidazole

CH3

N-Methyl carbamate

CH3NHCOR

N-Methylirnide

Methyl carboxylate

CHsCOR

: :

N-Methylcycloalkylamine

N-Methylcycloalkylarnine

(CH2I2

N4H3

Methylindole
H

W
Methylcyclohexane
H( + a -

Methyl ketone

CH&R

: :

Methylcyclohexene

C-CH3

N-Methylnitroarnine

xxiv

N-Methylnitrosamine

CH3rNO R

N-Methylpyridinium

Q
I
CH3

Methyloxazole

N-Methylpyridone

Met hy1p heny1

Met hylpyrimidine

Methylphosphinoyl

H3C-P-OR

PH

Methylpyrimidinone

CH30$ 0-Methylphosphorodithioate P-SR CH30 CH~O,$(~) P-SR CH,O (0)

N-Me t hylpyrrole

0-Methylphosphorothioate

N-Met hylpyrrolidine

N-Me t hylpiper azine

CHaN-NR

N-Me t hylpyrrolidone

N-Methylpiperidine

Methylquinoline

N-Methylpurine

Methylquinoxaline

Methylpyran

Methylsulfinyl

FH3

RNSOpR

Methylpyrazolinone

N-Me t hylsulfonamide

CH3SR

Methylpyridazine

Methyl sulf onat e

CH3OSO2R

Met hylpyridine

Methylsulfonyl

CHBSOPR

N-Methyltetrahydropyridine

0 0
;3 H ;a H

Nitrile

RCN

Methylthio ester

RCSCH,

II

Nitroalkyl

RCH2NQ

Methyl thioether

RSCH3

Nitrofuran

N-methyltriazene

RN=N-NCHa R

Nitroimidazole

[N 2 +O

N
H

N-Methyltriazinone

Nitrophenyl

Methyltriazole

Nitroquinoline

Met hyluracil
H

Nitrosamine

R "NO

' R

Monoclonal antibody

Nitrosourea

RNHCYR N=O

: :

Morphinan

Nucleoside

Morpholine

Octyl

Naphthalene

a
0

Oestradiol
HO

Naphthaquinone

@
0
R.
R'

Oestren-3-one
N-NO,

Nitramine

Oestrone

Pentyl

- HO
Pept ide Organoarsenic
R3h

RNHCCHNHCCHNH-

B : :
R
I

Organometallic complex, platinum

Phenol

Q
OS03H

Organoselenium

RSeR

Phenol sulfate

Orthoester

R-C-OR

OR I

OR

Phenothiazine

Oxadiazole

Phenoxyace t ate

Oxadiazolone

Phenoxybenzyl

Oxathiolane

Phenoxypropionate

Oxazole

Phenyl

Q-

Oxazolidinone

N-Phenyl

Oxime

RCH=NOH

P heny let hyl

Oximino

R=NOR

Phenylpyridine

Ozonide

RCHI CHR
\
0-0

Phenylurea

xxvii

Phosphonate

RO$

P-R RON

Platinum

Phosphoramide

RO$ P-NHR

Polycyclic aromatic

CHpOH

RNH'

Phosphoramidothioate

,P-OR RNH

R! O ,

Polycyclic aromatic amine

Phosphorodithioate

Polycyclic aromatic hydrocarbon

Phosphorothioate

ROJi

Ro/

P-SR

Prednisolone

do
9'
R2

Phthalazine Pregnadiene Ph t halazinone

0
N- N .

k
0

Phthalimide

Pregnene

Phthalidyl

d o
0

Prochiral carbon

R'-7*-R3

Piperazine

HN-Propyl

Piperazine dione

A0 RNYNR 0

Propy nyl

CHaCEC-

Piperidine

Pros t anoi d

Piperidinedione

Pteridine

xxviii

Purine

Pyrimidine
0

Pyrazine

Pyrimidone
R

Pyrazinone

Pyrrole

Pyrazole

Pyrrolidine

Pyrazolin-5-one
R

Pyrrolidine amide

Pyrazolopyr idine

Pyrrolidinone
R

Pyrene

Pyrrolidone

0
R

Pyridazine

Pyrrolizidine

Pyridazinone

Quinazolinedione

qxo
0

Pyridine

Quinoline

Pyridinium

Q
R

Quinolinone
R

Pyridone

0H

Quinolizidine

Pyridopyrimidine

Quinolone
R

mix

Quinone

()
0

Sydnone

Terpene Quinonedi-imine

CHF2CF2OR

Quinoneimine

6
NH

Te tr afluoroe t hy 1 ether

NH

Te trahydrobenzazepine
R

Quin oxaline

Tetrahydrocarboline
R

Steroid

Tetrahydrofuran

0
m N R

Sterol

Tetrahydroindazole

Sulfamic acid

RNHS03H

Tetrahydroisoquinoline

Sulfenamide

RS-NR,

Tetrahydronaphthalene

a
m R

Sulfonamide

RS02NHR

Tetrahydrophthalimide

Sulfonic acid

RSO3H

Tetrahydropyran

(2
R

N-Sulfonoxy

R~N-OSOSH

Tet rahydropyridine
R

Sulfonylurea

RSOZNHCNHR

Tetrahydropyridinium

0
R

Tetrahydropyridopyrirnidine

Thiirane

Tetrahydroquinoline

Thioarnide

RCNH,

Tetr azino ne

Thiobarbiturate
H

Tetr azole
R
N-S

2-Thiobenzothiazole

Thiadiazine

Thiadiazinone

CSko
N-NR

Thiocarbonyl

Thiadiazole

Thioke t a1

Thiazine

Thiomorpholine

SN nR

Thiazole

Thiophene
S

Thiazolidine
0

Thiophosphoramide

RZN-P-N

II

h .

R2

Thiazolidinone

rh
S\/N

Triazine

FN

kN!J
(. , N N

Thiazoline

Triazole

RN&

Thienylalkyl

Tr iazolopyridazine

N?NSN L N - 3

LN>

Thiocarbamate

RNHCS- X

Triazolopyrimidine Uracil
H

Tr ichloromet hyl

c(C113R

Trichothecene Trifluoromethylphenyl

m
F,c-(~

Ureide

RNHCNH,

: :

Vinca alkaloid

Xanthine
R

Trimethoxyphen y1

xxxii