A Simple Guide to the Nomenclature in Organic Chemistry

Nol P.G. Roeges, Marc O. De Moor

Contents
1 Paramount of the Substitutive Nomenclature
1.1 Common rules to build up a compound name 1.2 Numerical locants 1.3 Chemical functions arranged in descending order of priority 1.3.1 Cations 1.3.2 Acids and modifications 1.3.2.1 Acids 1.3.2.2 Anhydrides 1.3.2.3 Esters 1.3.3 Acid halides 1.3.4 Amides 1.3.5 Nitriles 1.3.6 Aldehydes 1.3.7 Ketones 1.3.8 Alcohols & phenols 1.3.9 Amines & imines 1.3.10 Functions as prefix only 1.4 Use of chemical functions and examples 1.4.1 Cations 1.4.2 Acids and modifications 1.4.2.1 Acids 1.4.2.2 Anhydrides 1.4.2.3 Esters 1.4.3 Acid halides 1.4.4 Amides 1.4.5 Nitriles 1.4.6 Aldehydes 1.4.7 Ketones 1.4.8 Alcohols & phenols 1.4.9 Amines & imines 1.4.10 Functions as prefix only 4 4 5 6 6 6 6 7 7 7 8 8 8 9 9 9 9 10 10 11 11 13 13 15 16 16 17 17 18 19 19 21 21 21 22 26 27 28 28 30 30 33

2 Molecular skeleton
2.1 Hydrocarbons 2.1.1 Acyclic and monocyclic hydrocarbons 2.1.2 Polycyclic hydrocarbons 2.1.3 Bridged structures 2.1.4 Fused rings with bridges 2.1.5 Spiro compounds 2.1.6 Connected identical rings 2.2 Compounds with heteroatoms 2.2.1 Chains 2.2.2 Monocyclic rings

2.2.3 Polycyclic heterocyclic systems 2.2.4 Heterocyclic bridged structures 2.2.5 Fused heterocyclic rings with bridges 2.2.6 Heterocyclic spiro compounds 2.2.7 Connected identical heterocyclic rings

36 40 40 41 41 42

3 Principal rules for the determination of skeletons in relation to the parent compound name 4 Rules for substituents and numbering 5 Names with multiple identical heading parents 6 Nomenclature with conjunctive parent compound names 7 Examples References

45 47 49 50

1
Paramount of the Substitutive Nomenclature
1.1 Common rules to build up a compound name [1,2] According to the substitutive nomenclature the parent compound name is formed by replacing hydrogen atoms by a functional group with the highest precedence ( 1.3 ), named principal function, as a suffix behind a basic molecular skeleton name. If necessary, this suffix has a multiplicative prefix and a locant fixing its position. This parent compound name becomes the heading parent. The remaining functions or fractions, not belonging to the heading parent, are substituents and become prefixes on this parent compound name with a numerical locant also.

prefix prefix prefix parent compound name

In the Chemical Substance Index of Chemical Abstracts [4] the compound names are inverted. The heading parent is printed bold face followed by a comma and the prefixes with locant in alphabetical order ( section 4.1 ). If appropriate, stereochemical and configurational descriptors are added at the end. Modifications by citing any derivatives are put behind the compound name with a space: ionic terms (chloride ), anhydride, ester, hydrazide, hydrazone, oxime, salt, inner salt, fragments covalently attached like N-oxide, other additive terms. Examples:
formula inverted name uninverted name
molecular skeleton

suffix

HO(O=)C-CH2-CH2-C N HO-CH2-CH2-CH2-C(=O)NH2 HO-CH2CH2-SH HO(O=)C-(CH2)4-C(=O)-NH-NH2

Propanoic acid, 3-cyano3-cyanopropanoic acid Butanamide, 4-hydroxy4-hydroxybutanamide Ethanol, 2-mercapto2-mercaptoethanol Hexanedioic acid monohydrazide

When no suffix is available to represent the preferred compound class ( section 1.3 ), and in that case only, molecular skeletons, chains or rings of atoms with only hydrogen atoms, themselves become the heading parent. Substituents are expressed as prefixes.
CH3CH2CH2CH=CH2 CH3-(CH2)4-O-Ph 1-pentene Benzene, pentyloxypentyloxybenzene

1.2 Numerical locants When numbers do not precede a skeleton, the numerical locant of the principal function is placed before the parent compound name.
HS-CH2-CH2-CH2-CH2-SH 1,4-Butanedithiol

N O O
3-pyridinecarboxylic acid, 1-oxide

OH

When a skeleton is already preceded by numbers, which designate the skeleton, the numerical locant of the principal function is placed between the name of the skeleton and the principal function.
CH2=CHCH(OH)CH3 CH3O-CH=CH-C(=O)CH3 3-Butene-2-ol 3-Butene-2-one, 4-methoxy4-methoxy-3-butene-2-one

1.3 Chemical functions arranged in descending order of priority ( representative examples, nonlimiting list ) Formula 1.3.1 Cations
cyclic a nomenclature cyclic not a nomenclature >N< =N< >O>S>P< -onia -ium ammonioiminiooxoniosulfoniophosphonio-aminium -iminium -oxonium (1) -sulfonium (1) -phosphonium (1)

Prefix

Suffix

1.3.2 Acids and modifications 1.3.2.1 Acids

-C(=O)OOH -(C)(=O)OOH -(C)(=S)SSH -C(=O)SSH -(C)(=O)SSH -(C)(=S)OOH -C(=O)OSH -C(=O)SOH -(C)(=O)OSH -(C)(=O)SOH -S(=O)2OOH -C(=O)OH -(C)(=O)OH -C(=S)SH -(C)(=S)SH -C(=S)OH ; -C(=O)SH -(C)(=S)OH ; -(C)(=O)SH -C(=N-NH2)OH -(C)(=N-NH2)OH -C(=NH)-OH -(C)(=NH)-OH -C(=NH)-SH -S(=O)2OH -S(=S)2SH -S(=S)2OH; -S(=O)(=S)SH -S(=O)2SH; -S(=O)(=S)OH -S(=O)(=NH-NH2)OH -S(=O)(=NH)OH -S(=O)OH -S(=S)SH (hydroperoxycarbonyl)-carboperoxoic acid -peroxoic acid -(dithioperoxo)thioic acid -carbo(dithioperoxoic) acid -(dithioperoxoic) acid -peroxothioic acid -carbo(thioperoxoic) acid -carbo(thioperoxoic) acid -(thioperoxoic) acid -(thioperoxoic) acid -sulfonoperoxoic acid -carboxylic acid -oic acid -carbodithioc acid -dithioic acid -carbothioic acid -thioic acid -carbohydrazonic acid -hydrazonic acid -carboximidic acid -imidic acid -carboximidothioic acid -sulfonic acid (3) -sulfonotrithioic acid -sulfonodithioic acid -sulfonothioic acid -sulfonohydrazonic acid -sulfonimidic acid -sulfinic acid -sulfinodithioic acid

[(thiosulfeno)carbonyl](thiosulfeno) oxo(mercaptooxycarbonyl)(sulfenocarbonyl)(mercaptooxy) oxosulfeno oxo(hydroperoxysulfonyl)carboxy-

(dithiocarboxy)-

(thiocarboxy)-

(hydrazonohydroxymethyl)hydrazono hydroxy(hydroxyiminomethyl)hydroxy imino(mercaptoiminomethyl)sulfo(trithiosulfo)(dithiosulfo)(thiosulfo)(hydrazonosulfo)(iminosulfo)sulfino(dithiosulfino)-

-S(=O)SH; -S(=S)OH -S(=N-NH2)OH -S(=NH)OH -SOH -SSH -P(=O)(OH)(O-OH) -P(=O)(OH)2 -P(=S)(SH)2 -P(=O)(SH)2 -P(=S)(OH)(SH) -P(=S)(OH)2 -P(=O)(OH)(SH) -P(=O)(OH)Cl -P(=O)(OH)(NH2) >P(=O)OH -HP(=O)OH >P(=S)SH >P(=S)OH >P(=O)SH -P(OH)2 -P(SH)2 -P(OH)(SH) >P-OH -HP-OH >P-SH

(thiosulfino)(hydrazonosulfino)(iminosulfino)sulfeno(thiosulfeno)(hydroperoxyhydroxyphosphinyl)phosphono(dimercaptophosphinothioyl)(dimercaptophosphinyl)(hydroxymercaptophosphinothioyl)(dihydroxyphosphinothioyl)(hydroxymercaptophosphinyl)(chlorohydroxyphosphinyl)(aminohydroxyphosphinyl)(hydroxyphosphinylidene)- (2) (hydroxyphosphinyl)(mercaptophosphinothioylidene)(hydroxyphosphinothioylidene)(mercaptophosphinylidene)(dihydroxyphosphino)(dimercaptophosphino)(hydroxymercaptophosphino)(hydroxyphosphinidene)(hydroxyphosphino)(mercaptophosphinidene)-

-sulfinothioic acid -sulfinohydrazonic acid -sulfinimidic acid -sulfenic acid -sulfenothioic acid -phosphonoperoxoic acid -phosphonic acid (1) (3) -phosphonotrithioic acid -phosphonodithioic acid -phosphonothioic acid -phosphonochloridic acid -phosphonamidic acid -phosphinic acid -phosphinodithioic acid -phosphinothioic acid -phosphonous acid -phosphonodithous acid -phosphonothious acid -phosphinous acid -phosphinothious acid

1.3.2.2 Anhydrides
-C(=O)-O-C(=O)-S(=O)2-O-C(=O)-R [(1-oxo R-oxy)-sulfonyl]acid anhydride ( with ) acid anhydride with

1.3.2.3 Esters
-C(=O)OR -(C)(=O)OR -S(=O)2OR -O-C(=O)-R -C(=S)OR -C(=O)SR -(C)(=S)OR -(C)(=O)SR (R-oxycarbonyl)R-oxy oxo(R-oxysulfonyl)1-oxo R-oxy(R-oxythioxomethyl)(R-thiocarbonyl)(R-oxythioxo)R-thio oxo R ...carboxylate R ...oate R-sulfonate

O-R thiocarboxylate S-R thiocarboxylate O-R thioate S-R thioate

1.3.3 Acid halides

F as example, followed by Cl > Br > I -C(=O)F -(C)(=O)F -C(=S)F chloro-; bromo-; iodo(fluorocarbonyl)fluoro oxo(fluorothioxomethyl)chloride ; bromide ; iodide -carbonyl fluoride -oyl fluoride -carbothioyl fluoride

-(C)(=S)F -C(=O)N3 -(C)(=O)N3 -C(=O)N=C=O -(C)(=O)N=C=O -C(=O)N=C=S -(C)(=O)N=C=S -C(=O)NC -(C)(=O)NC -C(=O)CN -(C)(=O)CN -C(=N-NH2)F -(C)(=N-NH2)F -C(=NH)F -(C)(=NH)F -S(=O)2F -S(=O)2-N=C=O -S(=O)2-N=C=S -S(=O)(=NH)F -S(=O)F -S-F -P(=O)F2 -P(=S)F2 -P(=O)(NH2)F >P(=O)F -PF2

fluoro thioxo(azidocarbonyl)azido oxo(isocyanatocarbonyl)isocyanato oxo(isothiocyanatocarbonyl)isothiocyanato oxo(isocyanocarbonyl)isocyano oxo(cyanocarbonyl)cyano oxo(fluorohydrazonemethyl)fluoro hydrazono(fluoroiminomethyl)fluoro imino(fluorosulfonyl)(isocyanatosulfonyl)(isothiocyanatosulfonyl)(fluoroiminosulfonyl)(fluorosulfinyl)(fluorosulfenyl)(difluorophosphinyl)(difluorophosphinothioyl)(aminofluorophosphinyl)(fluorophosphinylidene)(difluorophosphino)-

-thioyl fluoride -carbonyl azide -oyl azide -carbonyl isocyanate -oyl isocyanate -carbonyl isothiocyanate -oyl isothiocyanate -carbonyl isocyanide -oyl isocyanide -carbonyl cyanide -oyl cyanide -carbohydrazonoyl fluoride -hydrazonoyl fluoride -carboximidoyl fluoride -imidoyl fluoride -sulfonyl fluoride -sulfonyl isocyanate -sulfonyl isothiocyanate -sulfonimidoyl fluoride -sulfinyl fluoride -sulfenyl fluoride -phosphonic difluoride (1) -phosphonothioic difluoride -phosphonamidic fluoride -phosphinic fluoride -phosphonous difluoride

1.3.4 Amides
-C(=O)NH2 -(C)(=O)NH2 -C(=S)NH2 -(C)(=S)NH2 -C(=N-NH2)-NH2 -(C)(=N-NH2)-NH2 -C(=NH)-NH2 -(C)(=NH)-NH2 -S(=O)2NH2 -S(=O)NH2 -S-NH2 -P(=O)(NH2)2 >P(=S)(NH2)2 >P(=O)NH2 >P(=S)NH2 -P(=NH)(NH2)2 (aminocarbonyl)amino oxo(aminothioxomethyl)amino thioxo(aminohydrazonomethyl)amino hydrazono(aminoiminomethyl)amino imino(aminosulfonyl)(aminosulfinyl)(aminosulfenyl)(diaminophosphinyl)(diaminophosphinothioyl)(aminophosphinylidene)(aminophosphinothioylidene)(diaminophosphinimyl)-carboxamide -amide -carbothioamide -thioamide -carbohydrazonamide -hydrazonamide -carboximidamide -imidamide -sulfonamide -sulfimamide -sulfenamide -phosphonic diamide (1) -phosphonothioic diamide -phosphinic amide -phosphinothioic amide -phosphonimidic diamide

1.3.5 Nitriles
-C N -(C) N cyano-carbonitrile -nitrile

1.3.6 Aldehydes
-C(=O)H -(C)(=O)H -C(=S)H -(C)(=S)H formyloxo(thioxomethyl)thioxo-carboxaldehyde -al -carbothioaldehyde -thial

1.3.7 Ketones
=C=O ; >C=O >(C)(=O) =C=S >C=S >(C)(=S) carbonyl- (2) oxocarbonothioyl- (2) (thioxomethyl)thioxo-one

-thione

1.3.8 Alcohols & phenols

-OH -SH -O-OH -O-SH hydroxymercaptohydroperoxythiohydroperoxy-ol -thiol hydroperoxide (1) thiohydroperoxide

1.3.9 Amines & imines

-NH2 =N-H aminoimino- (2) -amine -imine

1.3.10. Functions as prefix only

-OR -SR -S(=O)R -S(=O)2R -F -Cl -Br -I -N3 -NO2 -NO -N=C=O -N=C=S -NC R-oxyR-thioR-sulfinylR-sulfonylfluorochlorobromoiodoazidonitronitrosoisocyanatoisothiocyanatoisocyano-

Other prefixes with exclusively heteroatoms ( N, P, Si ) : section 2.2.1 table 2.7

(1) Phosphorus and hydroperoxide suffixes and some cations are treated as functional parent compounds not based on a molecular skeleton. Parent names such as hydroperoxide and thiohydroperoxide are separated from the suffix with a space in the uninverted name according to the radicofunctional nomenclature. In the inverted name the suffix gets no hyphen.
CH3CH2CH2CH2-P(=O)(OH)2 CH3CH2CH2-O-O-H Phosphonic acid butylbutylphosphonic acid Hydroperoxide propyl propyl hydroperoxide

(2) Multiplying radicals : table 5.1 (3) Selenium ( seleno, selenyl ) and tellurium ( telluro, tellurinyl ) compounds are named similar to sulfur compounds. Arsenic ( arsino, arsinyl, arsinidene ) compounds are named similar to phosphorus compounds.

1.4 Use of chemical functions, examples 1.4.1 Cations In cyclic cations named by the replacement nomenclature the a becomes onia
OH N Br
5-azoniaspiro[4.5]decane, 2-hydroxy- bromide 2-hydroxy-5-azoniaspiro[4.5]decane bromide

Other cyclic cations and acyclic molecular skeletons get the suffix ium with the (lowest) locant if necessary.
CH2 CH3 O Cl

Furanium, 1-ethyl- chloride 1-ethylfuranium chloride

O O

CH3 Cl

1,3-Dioxol-1-ium, 2-methyl- chloride 2-methyl-1,3-dioxol-1-ium chloride

Ethanaminium, N,N,N-trimethyl-2-sulfo- inner salt

10

O O S O

CH3 CH2CH2 N CH3 CH3

CH3 P CH3 O CH3 C O
N,N,N-trimethyl-2-sulfoethanaminium inner salt

CH3CH2 CH3

Phosphonium, ethyltrimethyl- acetate ethyltrimethylphosphonium acetate

Retained trivial names

Pyrylium

O
2H-Furylium

1.4.2 Acids and modifications 1.4.2.1 Acids Acyclic monoacids and diacids get the suffix oic acid.
HO-CH2-C(=O)-O-O-H Ethaneperoxoic acid, 2-hydroxy2-hydroxyethaneperoxoic acid Benzenecarboperoxoic acid, 4-carboxy4-carboxybenzenecarboperoxoic acid

O HO C
CH3O

O C O O H

O CH3O CH3O
HO(O=)C-CH2-CH2-CH2-CH2-S(=O)OH Pentanoic acid, 5-sulfino5-sulfinopentanoic acid Propanoic acid, 3-(hydroxyphosphinyl)-2-oxo3-(hydroxyphosphinyl)-2-oxopropanoic acid

Benzenecarbo(dithioperoxoic) acid, 3,4,5-trimethoxy3,4,5-trimethoxybenzenecarbo(dithioperoxoic) acid

O HO PH CH2

O O C C OH

CH3-C(=O)-S-CH2-CH(CH3)-C(=O)-SH

Propanethioic acid, 3-(acetylthio)-2-methyl3-(acetylthio)-2-methyl-propanethioic acid

O H HO C C

O CH2 C OH
Butanedioic acid, 2-formyl2-formylbutanedioic acid

C O H

11

The suffix carboxylic acid is used for a chain with more than two carboxyl groups (section 4.6 ) or a carboxylgroup attached to a heteroatom and for compounds in which the carboxyl group is attached to a ring.
O HO C C N
Cyclopentanecarboxylic acid, 3-cyano-4-methylene3-cyano-4-methylenecyclopentanecarboxylic acid

CH2
O CH3 C NH O C SH
Benzenecarbothioic acid, 4-acetylamino4-acetylaminobenzenecarbothioic acid

H2P-C(=O)OH

Phosphinecarboxylic acid

O HO C N N

O C OH
1,2-Diazenedicarboxylic acid

Retained trivial names of the most important carboxylic acids:

HC(=O)OH CH3C(=O)OH PhC(=O)OH HO-C(=O)-OH Cl-C(=O)-OH N C-OH N C-C(=O)OH H2N-C(=O)OH N C-SH H2N-C(=S)SH formic acid acetic acid benzoic acid carbonic acid carbonochloridic acid cyanic acid carbonocyanidic acid carbamic acid thiocyanic acid carbamodithioic acid

The amino acids such as alanine, arginine, glycine,

S HO P OH
S H2N C

O CH2 C OH

Acetic acid, 2-(dihydroxyphosphinothioyl)2-(dihydroxyphosphinothioyl)acetic acid

O C OH

Benzoic acid, 4-(aminothioxomethyl)4-(aminothioxomethyl)benzoic acid

OH P O O OH

Phosphonic acid, 2-furanyl2-furanylphosphonic acid

HO(O2)S-CH2-CH2-C(=O)NH2

Propanesulfonic acid, 3-amino-3-oxo3-amino-3-oxopropanesulfonic acid

12

O C NH

O S O SH
Benzenesulfonothioic acid, 4-benzoylamino4-benzoylaminobenzenesulfonothioic acid

Retained names of frequently used mineral acids

N(=O)2-OH N(=O)-OH S(=O)2(OH)2 S(=O)2(OH)(NH2) S(=O)(OH)2 P(=O)(OH)3 P(=S)(OH)3; P(=O)(OH)2(SH) P(=O)(OH)2(NH2) P(=O) (OH) (NH2)2 P(=O) (SH) (NH2)2 P(=O)(OH)(CN)(NH2) P(=O)(OH)2Cl P(OH)3 P(OH)2(SH) P(=O)OH P(=S)SH nitric acid nitrous acid sulfuric acid sulfamic acid sulfurous acid phosphoric acid phosphorothioic acid phosphoramidic acid phosphordiamidic acid phosphoramidothioic acid phosphoramidocyanic acid phosphorochloridic acid phosphorous acid phosphorothious acid phosphenous acid phosphenodithious acid

Hydrazides: The OH (SH) of an acid becomes NH-NH2

-C(=O)OH becomes -C(=O)NH-NH2 CH3CH2CH2-C(=S)-NH-NH2 H2N-NH-C(=O)CH3 Butanethioc acid, hydrazide Acetic acid, hydrazide

1.4.2.2 Anhydrides Anhydrides, with the exception of the cyclic ones and those named by the replacement nomenclature, are predominantly considered as modifications of an acid. Symmetric anhydrides take anhydride . Non symmetric anhydrides take anhydride with , monoanhydride with
O CH3 C O
O HO C

O S O O CH3
O O C CH3 Propanedioic acid, monoanhydride with acetic acid
Acetic acid, anhydride with methanesulfonic acid

CH2 C

Anhydride prefix as substituent on a compound with preferred function:

O CH3CH2 O O O C OH
Benzoic acid, 4-[(1-oxopropoxy)sulfonyl]4-[(1-oxopropoxy)sulfonyl]benzoic acid

C O S

13

Retained trivial names of anhydride prefixes:

R : methoxy, ethoxy, propoxy, butoxy, phenoxyCH3-C(=O)-O-C(=O)CH3-C(=O)-O-S(=O)2[(acetyloxy)carbonyl][(acetyloxy)sulfonyl]-

1.4.2.3 Esters Esters, other than cyclic esters or lactones, are considered usually as derivatives of an acid, but as a derivative of an alcohol, thiol or phenol in the case of an ester derived from a common acid ( acids class I ) and an either rare alcohol or phenol ( alcohols class II ) [3].
O CH3 C C O CH2CH3 O H C C O CH2CH3
2-Butenedioic acid, 2-methyl- (2Z)- ethyl ester Ethyl (2Z)-2-methyl-2-butenedioate

O CH3CH2 O P OH OH
O Cl P O O CH2CH3 CH2CH3
Phosphorochloridic acid diethyl ester diethyl phosphorochloridate Phosphoric acid monoethyl ester ethyl dihydrogen phosphate

O P

O CH2CH3 S CH3

Phosphonothioic acid, cyclohexyl- O-ethyl-S-methyl ester cyclohexylphosphonothioic acid O-ethyl-S-methyl ester

O CH3 C

(CH2)3 CH3 O CH2 CH (CH2)5 CH3

2-Butyl-1-octanol acetate 2-butyl-1-octyl acetate

O H C O CH2CH2 O

O C H

1,2-Ethanediol diformate 1,2-ethanediyl diformate

Ester prefix as substituent on a compound with preferred function.

O C O CH3 O C O (CH2)4CH3
benzoic acid, 2-(1-oxopentyloxy)- methyl ester methyl 2-(1-oxopentyloxy)benzoate

14

O C OCH3 CH CH C O OCH3
benzoic acid, 2-(3-methoxy-3-oxo-1-propenyl)methyl ester methyl 2-(3-methoxy-3-oxo-1-propenyl)benzoate

O
Cyclopentanone, 3-(benzoyloxy)3-(benzoyloxy)cyclopentanone

Retained trivial names used in ester prefixes:

R : methoxy-, ethoxy-, propoxy-, butoxy-, phenoxyCH3-C(=O)-OExample : CH3-CH2-C(=O)-O(1-oxopropoxy)(acetyloxy)-

Examples of retained trivial names of esters of mineral acids:

N(=O)2-O-R N(=O)-O-R S(=O)2(OH)(OR) S(=O)2(OR)2 S(=O)(OR)2 P(=O)(OH)2(OR) P(=O)(OR)3 P(OR)3 P(=S)(OR)3 R nitrate R nitrite R hydrogen sulfate di-R sulfate di-R sulfite R dihydrogen phosphate tri-R phosphate tri-R phosphite O,O,O-tri-R phosphorothioate

CH3CH2 O CH3CH2 O

S P O NO2
Phophorothioic acid, O,O-diethyl O-(4-nitrophenyl) ester O,O-diethyl O-(4-nitrophenyl) phosphorothioate

1.4.3 Acid halides

F-C(=O)-CH2-CH2-C(=O)I Butanoylfluoride, 4-iodo-4-oxo4-iodo-4-oxobutanoylfluoride

O H2N C

O C N C O
Cyclopentanecarbonylisocyanate, 3-(aminocarbonyl)3-(aminocarbonyl)cyclopentanecarbonylisocyanate

Cl-(=O)-(CH2)4-C(=O)Cl

Hexanedioyl dichloride

15

N OH C Cl

Benzenecarboximidoyl chloride, N-hydroxyN-hydroxybenzenecarboximidoyl chloride

Cl CH3 C CH2 CH3 PCl2

Phosphonous dichloride, (2-chloro-2-methylpropyl)(2-chloro-2-methylpropyl)phosphonous dichloride

Examples of retained trivial names of acid halogenides:

CH3C(=O)Cl PhC(=O)Cl Cl-C(=O)-Cl Cl-C(=S)-Cl H2N-C(=O)-Cl acetylchloride benzoylchloride carbonic dichloride carbonothioic dichloride carbamic chloride

Some halogenides derived from mineral acids:

S(=O)2Cl2 S(=O)2(NH2)Cl S(=O)Cl2 P(=O)Cl3 P(=O)(NH2)Cl2 P(=S)(NH2)Cl2 sulfuryl chloride sulfamoyl chloride thionyl chloride phosphoric trichloride phosphoramidic dichloride phosphoramidothioic dichloride

S Cl P Cl N

CH3 CH3

Phosphoramidothioic dichloride, dimethyldimethylphosphoramidothioic dichloride

1.4.4 Amides
O CH 3 (CH2)16 CH3 (CH2)16 C C NH
Octadecanamide, N-(1-oxooctadecyl)N-(1-oxooctadecyl)octadecanamide

O H-C(=S)-CH2-CH2-C(=S)NH2

Butanethioamide, 4-thioxo4-thioxobutanethioamide

Amides in which the nitrogen atom of the amide group is part of a heterocyclic ring (unexpressed amides ) are named at the highest ranking function present. [10]

O CH3CH2 C N
1-Propanone, 1-(1-piperidinyl)1-(1-piperidinyl)-1-propanone

Examples of substituted amide prefixes:

CH3-NH-C(=O)Ph-NH-C(=O)H2N-NH-C(=O)[(methylamino)carbonyl][(phenylamino)carbonyl](hydrazinocarbonyl)-

16

Some retained trivial names of amides, thioamides and amides of mineral acids:
HC(=O)NH2 C(=O)NH2 PhC(=O)NH2 H2N-C(=O)-NH2 H2N-C(=S)-NH2 S(=O)2(NH2)2 S(=O)(NH2)2 P(=O)(NH2)3 P(=S)(NH2)3 P(NH2)3 P(=O)NH2 P(=S)NH2 H2N-C(=NH)-NH2 formamide acetamide benzamide urea thiourea sulfamide sulfurous diamide phosphoric triamide phosphorothioic triamide phosphorous triamide phosphenous amide phosphenothious amide guanidine

1.4.5 Nitriles
HO-CH2CH2-C N Propanenitrile, 3-hydroxy3-hydroxypropanenitrile

Cyclohexanecarbonitrile, 4-carbonothioyl4-carbonothioylcyclohexanecarbonitrile

Retained trivial names of nitriles:

CH3C N PhC N acetonitrile benzonitrile

1.4.6 Aldehydes Acyclic mono and dialdehydes get the suffix (thi)al The suffixes carboxaldehyde and carbothioaldehyde are used for a chain with more than two aldehyde groups ( section 4.6 ) and for such groups attached to a ring.
HO-CH2-CH2-CH2-C(=O)H H(S=)C-CH2-CH2-CH2-CH(OCH3)-C(=S)H Butanal, 4-hydroxy4-hydroxybutanal Hexanedithial, 2-methoxy2-methoxyhexanedithial Cyclohexanecarbothioaldehyde, 4-(trifluoromethyl)4-(trifluoromethyl)cyclohexanecarbothioaldehyde

S CF 3 C H

Retained trivial names of aldehydes:

HC(=O)H CH3C(=O)H PhC(=O)H formaldehyde acetaldehyde benzaldehyde

17

1.4.7 Ketones
(CH3CH2)N-CH2-CH2-CH2-C(=O)CH3 2-Pentanone, 5-diethylamino5-diethylamino-2-pentanone

Examples of substituted prefixes:

CH3CH2-C(=O)CH2=CH-C(=O)HC C-C(=O)CH3-C(=O)-CH2-C(=O)H2N-CH2-CH2-C(=O)HO(O=)C-C(=O)CH3-C(=S)Ph-C(=S)(1-oxopropyl)(1-oxo-2-propenyl)(1-oxo-2-propynyl)(1,3-dioxobutyl)(3-amino-1-oxopropyl)(carboxycarbonyl)(1-thioxoethyl)(phenylthioxomethyl)-

S CH3 C

O C NH2
Cyclohexanecarboxamide, 4-(1-thioxoethyl)4-(1-thioxoethyl)cyclohexanecarboxamide Benzoic acid, 4-(phenylthioxomethyl)4-(phenylthioxomethyl)benzoic acid

S C

O C OH

Examples of retained trivial names of prefixes:

CH3C(=O)HOCH2-C(=O)H2NCH2-C(=O)HC(=O)-C(=O)Cl-C(=O)-C(=O)CH3CH2-O-C(=O)-C(=O)H2N-C(=O)-C(=O)PhC(=O)2-H2N-Ph-C(=O)acetyl(hydroxyacetyl)(aminoacetyl)(oxoacetyl)(chlorooxoacetyl)(ethoxyoxoacetyl)(aminooxoacetyl)benzoyl(2-aminobenzoyl)-

O C

O C OH

Benzoic acid, 4-benzoyl4-benzoylbenzoic acid

Derivatives of aldehydes and ketones: Oximes : >C=O becomes >C=N-OH Hydrazones : >C=O becomes >C=N-NH2
(CH3)2C=N-OH : 2-propanone oxime

18

1.4.8 Alcohols & phenols

CH2OH H2 N C CH2OH CH2OH
CH3CH2CH2CH2-SiH2-OH 1,3-Propanediol, 2-amino-2-(hydroxymethyl)2-amino-2-(hydroxymethyl)-1,3-propanediol

Silanol, butylbutylsilanol

Retained trivial names:

Monosaccharides such as D-glucose, D-fructose, D-galactose, phenol

HO CH CH CH2 CH2OH
Phenol, 3-(4-hydroxy-1-butenyl)3-(4-hydroxy-1-butenyl)phenol

Prefixes are used when hydroxy and mercapto groups ( and estergroups) are attached to hetero atoms other than silicon.
Ph-N=N-N(OH)CH3 1-Triazene, 3-hydroxy-3-methyl-1-phenyl3-hydroxy-3-methyl-1-phenyl-1-triazene 1H-Pyrrole, 1-mercapto1-mercapto-1H-pyrrole

SH N

O NH O C CH3
Benzenamine, N-acetyloxyN-acetyloxybenzenamine

1.4.9 Amines & imines

(CH3)2HC-NH-CH(CH3)2 Ph-NH-Ph 2-Propanamine, N-(1-methylethyl)N-(1-methylethyl)- 2-propanamine Benzenamine, N-phenylN-phenylbenzenamine 1-Propanimine, 2,2-dimethyl2,2-dimethyl-1-propanimine

(CH3)3C-CH=NH

Examples of substituted amino prefixes:

CH3-NH(CH3CH2)2NPh-NHHOSO2NHNC-NHHO-NHO2N-NHO=N-NHCH3-CH2-C(=O)-NH(methylamino)(diethylamino)(phenylamino)(sulfoamino)(cyanoamino)(hydroxyamino)(nitroamino)(nitrosoamino)[(1-oxopropyl)amino]-

19

H2N-C(=O)-NHPh-C(=S)-NHH2N-C(=NH)-NH(H3Si)2N-

[(aminocarbonyl)amino][(phenylthioxomethyl)amino][(aminoiminomethyl)amino](disilylamino)-

Retained trivial names:

H(C=O)-NHCH3-C(=O)-NHH2N-C(=O)-C(=O)-NHPh-C(=O)-NHCH3-C(=O)-N= Ph-C(=O)-N= (formylamino)(acetylamino)[(aminooxoacetyl)amino](benzoylamino)(acetylimino)(benzoylimino)-

1.4.10 Functions as prefix only

O2N O C Cl CH C O

1-Propene-1,3-dione, 3-(3-chloro-5-nitrophenyl)3-(3-chloro-5-nitrophenyl)-1-propene-1,3-dione

S C SH S O CH3
Benzenecarbodithioic acid, 2-(methylsulfinyl)2-(methylsulfinyl)benzenecarbodithioic acid

Examples of substituted oxy compounds:

CH3(CH2)4-OH3Si-Opentyloxy(silyloxy)-

Retained trivial names:

CH3-OCH3CH2-OCH3CH2CH2-OCH3(CH2)3-OPh-Omethoxyethoxypropoxybutoxyphenoxy-

C N N C O
Benzene, 2,4-diisocyanato-1-methoxy2,4-diisocyanato-1-methoxybenzene

CH3O

20

2
Molecular skeleton
A molecular skeleton consists of a chain or a ring of atoms, on which only hydrogen atoms are bound. Hydrocarbons are made up of only carbon atoms in the skeleton, while heterocycles have atoms other than carbon also. 2.1 Hydrocarbons 2.1.1 Acyclic and monocyclic hydrocarbons Acyclic hydrocarbons : Alkanes receive the ending ane Alkenes receive the ending ene, or adiene, atriene, with appropriate locants Alkynes receive the ending yne, or adiyne, atriyne, with appropriate locants Monocyclic hydrocarbons take the same name as the corresponding acyclic compound plus the prefix cyclo. ( except. : benzene )

Table 2.1. Alkanes

Formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3(CH2)3CH3 CH3(CH2)4CH3 CH3(CH2)5CH3 CH3(CH2)6CH3 CH3(CH2)7CH3 CH3(CH2)8CH3 CH3(CH2)9CH3 CH3(CH2)10CH3 CH3(CH2)11CH3 CH3(CH2)12CH3 CH3(CH2)13CH3 CH3(CH2)14CH3 Name methane ethane propane butane pentane hexane heptane octane nonane decane undecane dodecane tridecane tetradecane pentadecane hexadecane Formula CH3(CH2)15CH3 CH3(CH2)16CH3 CH3(CH2)17CH3 CH3(CH2)18CH3 CH3(CH2)19CH3 CH3(CH2)20CH3 CH3(CH2)21CH3 CH3(CH2)22CH3 CH3(CH2)23CH3 CH3(CH2)28CH3 CH3(CH2)29CH3 CH3(CH2)30CH3 CH3(CH2)31CH3 CH3(CH2)38CH3 CH3(CH2)48CH3 CH3(CH2)98CH3 Name heptadecane octadecane nonadecane eicosane heneicosane docosane tricosane tetracosane pentacosane triacontane hentriacontane dotriacontane tritriacontane tetracontane pentacontane hectane

21

Table 2.2. Hydrocarbon radicals as prefixes attached to one atom. For multiplying radicals see table 5.1. Hydrocarbon ending -ane -ene -yne monovalent prefix ending -yl -enyl -ynyl divalent trivalent prefix ending prefix ending -ylidene -enylidene -ynylidene -ylidyne -enylidyne -ynylidyne

Retained trivial names : phenyl, methylene Examples of prefixes: Monovalent prefix divalent prefix
CH2= CH3CH= CH3CH2CH= CH2=C= CH3-CH=C= CH2=CH-CH= CH C-CH= methyleneethylidenepropylidene ethenylidene1-propenylidene2-propenylidene2-propynylidene-

trivalent prefix
HC CH3-C CH3-CH2-C methylidyneethylidynepropylidyne-

CH2=CHethenylCH3-CH=CH1-propen-1-ylCH2=CH-CH22-propen-1-ylHCCethynylCH3-C C1-propyn-1-ylHC C-CH22-propyn-1-ylCH2=CH-CH=CH- 1,3-butadien-1-yl-

Examples of substituted prefixes:

Ph-CH2HO(O=)C-CH2HO-CH2H2N-CH2Cl-CH2Ph-C(=O)-CH2CH3-C(=O)-CH2(CH3)2CH(CH3)3CH-C(=NH)Ph-C(=NH)Ph-C(=NOH)H2N-NH-C(=NH)CH3-C(=NH)CH3-C(=NOH)(phenylmethyl)(carboxymethyl)(hydroxymethyl)(aminomethyl)(chloromethyl)(2-oxo-2-phenylethyl)(2-oxopropyl)(1-methylethyl)(1,1-dimethylethyl)(iminomethyl)(iminophenylmethyl)[(hydroxyimino)phenylmethyl](hydrazinoiminomethyl)(1-iminoethyl)[1-(hydroxyimino)ethyl]Ph-CH= Ph2C= CH3CH2-C(CH3)= Ph-CH=CH-CH= (CH3)2C= 2-HO-Ph-CH= Ph-C (phenylmethylene)(diphenylmethylene)(1-methylpropylidene)(3-phenyl-2-propylidene)(1-methylethylidene)[(2-hydroxyphenyl)methylene](phenylmethylidyne)-

2.1.2 Polycyclic hydrocarbons. For the nomenclature of these cyclic compounds we refer to specialised literature such as Index of Ring Systems [5], Parent Compound Handbook [6] or Chemical Substance Index of Chemical Abstracts [4]. About twenty trivial names are used ( table 2.3 ). For radicals, the suffix ene changes to enyl and the locants of attachment have to be indicated. A concise summary for the nomenclature of fused polycyclic ring assemblies: Fused systems contain at least two five or more membered rings. The rings have at least two adjacent atoms in common. Therefore, a bicyclic system with a four or three membered ring is interpreted as a bridged system ( section 2.1.4) .

22

The total system is oriented so that a maximum number of rings is in a horizontal row with a maximum number in the upper right quadrant. Numbering begins clockwise with the atom next to the fused bond on the ring situated most right in the upper right quadrant. The locants of the fused atoms are derived from those of the preceding no fused positions by addition of the characters a,b,c, etc, When, a further choice is needed for orientation and numbering, atoms in fused positions are assigned with the lowest numbers. - linearly fused benzenoid rings: Five rings or more: multiplicative prefix + acene, but retained names are: naphthalene(two rings),
anthracene(three) and naphthacene(four) see also table 2.3
11 1 2 9 7 5 3 4

pentacene

4a

- angular fused benzenoid rings with five or more rings: multiplicative prefix + phene; retained name: phenanthrene(three rings)
2 1 3 4

5 11

pentaphene

alternated fused benzene ( naphthalene) rings: multiplicative prefix + phenylene (naphthylene)

8 1

biphenylene
5 4

two identical monocyclic ring systems : multiplicative prefix + alene

1
1

pentalene
4 3
5 4

except. : naphthalene

The most unsaturated compound only is named in this way. The more saturated compounds have, according to the additive nomenclature, the same name with the prefix di-, tetra-, hexa-, octa-, deca-, ... hydro-, preceded by the numerical locant of saturation.
octahydropentalene 1,2,3,4-tetrahydronaphthalene

- general method to build fused ring systems : The basic component is the ring system with the largest number of rings, the ring system

23

with the largest individual ring ( except benzindene) or the most linear ring system.
1
8 1

9 3
3 5

1H-benz[f]indene

1H-benz[e]indene

The place(s) on which the other ring(s) are fused, are indicated with a letter ( letter indication ). The small letter a means the bond between the atoms 1 en 2 of the basic component. Preference is given to the lowest alphabetical letter. The rings which are fused to the basic component have to be of minor complexity and the suffix 'ene' changes to 'eno' , example: pentaleno, indeno, except.: benzo, naphtho, anthra, cyclopenta,... The name is attributed to the most unsaturated compound. The atoms by which the rings are fused, have to be indicated by numbers and the lowest possible combination of numbers is applied. ( number indication ).
18 1

1
1

12 10 9 a 5

13

2' a

1' 4

4a 5 4

benzocyclo-octene

benz[a]anthracene

anthra[2,1-a]naphthacene

An indicated hydrogen, necessary to the formation of a definable ring, is named at the lowest numbered position if there is no favoured position ( additive nomenclature ). O 9
1

O
4

1H-cyclopenta[b]anthracene
1 13a 4a 12a 11 10 8a 7a 12b 12c 5a 5

1H-indene-1-one

2H-indene-2-one (derived from 2H indene)

1

13a 4a 11a 10 9 7a 6a 12a 12b 4b

1H-indeno[1,2-a]anthracene

1H-indeno[2,1-a]anthracene

24

11

10

13

2 8 m n a 3

4b 7

4a 4

1H-indeno[1,2-b]anthracene

1H-indeno[6,7,1-mna]anthracene

Extra hydrogen or added hydrogen is necessary sometimes to permit the expression of a principal function as a suffix instead of a prefix and to make possible the appropriate heading parent.
O
1 2

1H-indene-1,3-(2H)-dione
3

Table 2.3. Retained trivial names of polycyclic hydrocarbons [7] .

8
8 7 6 5 4 1 2

1 2

6
3

3 5 10 4

naphthalene
12 1 2
7 8 9 10 1 2

anthracene

10 9 8 7

11

3 6 5 4

phenanthrene
3

naphthacene
2

3
2

12

1 14 13
3

9 4 8

12

chrysene
1
2

5 6

picene

10 9

12 11 4

pyrene

10

perylene
5

H 2C
9

3 1

7 6
4

H2 C

1H-phenalene

1H-indene

25

8 7 6

1 2
7 8

H2 C
9

1 2 3

3
6

azulene
1 8
6 2

9H-fluorene

7
5 3

s-indacene

as-indacene
3

2
1

10 4

acenaphthylene
2
10 1 3

fluoranthene

1 10 9 9 8 8

aceanthrylene
1 9 2
1 2 3

acephenanthrylene

1H-trindene
2
14 1 3

pleiadene

11

10 10

99

coronene
2

6 11

rubicene
2

1 11

11

11

10

10

pyranthrene

ovalene

The names of steroids such as androstane, pregnane, are retained also and are derived from 1Hcyclopenta[a]phenanthrene with typical locants:
12 11 1 2 3 4 5 6 9 10 14 8 7 15 13 16 17

26

2.1.3 Bridged structures are named according to the Von Baeyer nomenclature: prefix bicyclo, tricyclo ... ( alicyclic rings ) The name of a polycyclic system ( bicyclic, tricyclic, ) is equal to the number of bonds that has to be broken in order to obtain an open chain. The principal bridge is the largest one.
.
1 7 8 6 5 4 3 2

three atoms in the largest bridge two atoms in the second largest bridge one atom in the shortest bridge numbering starts with the bridgehead, running through the longest bridge.

bicyclo[3.2.1]octane
1
1 2

5 4
4

1 2

6 5

bicyclo[2.2.2]octane

tricyclo[3.1.0.02,4]hexane

bicyclo[4.2.0]octa-1,3,5,7-tetraene

The principal bridge has to divide the principal ring as symmetrical as possible.
14 1 5

13

10

heptacyclo[8.6.0.02,9.03,8.04,7.011,16.012,15]hexadecane

However, bicyclic compounds that are composed of rings with at least five atoms and a bridge of zero atoms, are treated as fused compounds ( section 2.1.2 ).
octahydropentalene, decahydronaphthalene

2.1.4 Fused rings with bridges : common suffixes : ano, eno Table 2.4 Examples of bridges :
>C< : methyno >CH-CH< : ethanediylidene -CH2-CH< : ethanylylidene -CH2-CH2-CH<: 1-propanyl-3-ylidene -Ph- : benzeno

-CH2- : methano -CH2-CH2- : ethano >C- : metheno -CH=CH- : etheno -CH2-CH=CH-CH2-: 2-buteno

Examples of bridges with hetero atoms see section 2.2.6, table 2.11 .
8 1
8 1

decahydro-1,4-methanonaphthalene

1,4-ethenoanthracene

27

12

1
14

2 12 3

11
11 8 9 1

7
5 10 4

9,10-dihydro-9,10[1',2']benzenoanthracene ( special numbering system for anthracene )

1,6,2,5ethanediylidenebenzo[a]cyclobuta[c]cyclooctene

2.1.5 Spiro compounds Spiro compounds hold one carbon atom in common between two rings: the spiro atom ; prefix : spiro. Alicyclic rings :
three atoms in the smallest ring (spiro atom is not included ) four atoms in the larger ring numbering starts with the smallest ring next to the spiro atom
1 2 3
8 7 6 1 2 5 4 3
7 2 9 10 8 6 3 5 4 1

5 6 4 7 8

10

spiro[3.4]octane

spiro[4.5]deca-1,6-diene

dispiro[2.2.2.2]decane

Bridged systems : component names are retained

4' 1
1 2 1' 7 3' 2'

5' 5 1' 4

5,5-spirobi[bicyclo[2.1.0]pentane]

spiro[bicyclo[3.1.1]heptane-2,1-cyclopropane]

Fused ring systems : component names are retained

4' 1 3'

1'

2 3

2' 1'

2'

1 5

4'

3'

2,2-spirobi[2H-indene]

spiro[cyclopentane-1,2-[2H]indene]

28

2.1.6 Connected identical rings Placing the prefix bi, ter, quater, quinque, sexi, septi, octi, novi or deci in front of the hydrocarbon name, forms the name of the connected ring but for connected benzenoid rings, phenyl is used instead of benzene. The numbers without an accent belong to the ring with the lowest number of attachment. For couples of monocyclic hydrocarbons the prefix bi is attached to the name of the radical (cycloalkanes, cycloalkenes ).

2 1 2' 1'

1'

1,2-binaphtalene

1,1-biphenyl

1,1-bicyclohexyl

1,1-bicyclopropyl

1'

4'

1"

1,1: 4,1: 4,1-quatercyclohexane

1,1:4,1-terphenyl

29

2.2

Compounds with heteroatoms

2.2.1 Chains Carbon chains with at least four heteroatoms, which dont belong to the principal function and are situated in the longest chain, are treated according to the replacement nomenclature ( a nomenclature ). The lowest locants are assigned to the functional suffixes and no longer to the replacement prefixes. If there are less than four heteroatoms in the chain, the substitutive nomenclature is used. Table 2.5. Replacement prefixes in descending order of precedence. Element oxygen sulfur selenium nitrogen phosphorus silicon
Examples: CH3-S-CH2-S-CH2CH2-S-CH2-S-CH2-S-CH3 : 2,4,6,9,11-pentathiadodecane CH3(OCH2CH2)4OCH3 : 2,5,8,11,14-pentaoxapentadecane CH3O-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-OH : 3,6,9,12-tetraoxatridecanol H2N-(CH2CH2NH)4-CH2CH2-NH2 : 3,6,9,12-tetraazatetradecane-1,14-diamine

Symbol O S Se N P Si

Prefix oxathiaselenaazaphosphasilaoxthiselenazphosphsil-

Valence 2 2 2 3 3 4

The name of the molecular skeleton of chains which exclusively contain heteroatoms, is based on the name of the monoatomic hydride or mixed hydride and gets a multiplicative prefix indicating the number. (except.: H2N-NH2 hydrazine ) Table 2.6. Name of some hydride-units. atoms N P3+ P5+ Si N + Si O + Si S + Si unit NH3 PH3 PH5 SiH4 H3Si-NH2 H3Si-OH H3Si-SH saturated unsaturated

azane azene phosphine phosphene phosphorane phosphorene silane silene silazane silazene siloxane silathiane

30

Examples: H2N-NH-NH-NH2 tetrazane H2N-NH-NH-NH-NH2 pentazane H2N-(NH)6-NH2 octazane H2N-N=N-NH2 2-tetrazene H2P-PH-PH2 triphosphine HP=P-PH2 1-triphosphene H4P-PH4 diphosphorane H3P=PH=PH3 1,2-triphosphoradiene H3Si-(SiH2)3-SiH3 pentasilane H2Si=SiH-SiH3 trisilene H3Si-O-SiH2-O-SiH3 trisiloxane H3Si-[O-SiH2]3-O-SiH3 pentasiloxane H3Si-S-SiH3 disilathiane H3Si-NH-SiH3 disilazane

Table 2.7. Representative examples of radicals with exclusively hetero atoms, non limiting list.[10]
nitrogen H2N-NH-NH-HN-NHHN=N-N=NH2N-NH-N=NH2N-NHH2N-C(=O)-NH-NHH2N-N= N-=N+=N- (N3- ) N-=N+= (N2= ) triazanyl1,2-hydrazinediyl- previous hydrazodiazenyl1,2-diazenediyl- previous azo1-tetrazenylhydrazinyl- previous hydrazino[2-(aminocarbonyl)hydrazinyl]hydrazinylidene- previous hydrazonoazidodiazo3H-diazirine previous azi(component ring in a spiro name) diaziridine previous hydrazi(component ring in a spiro name) phosphinophosphinidenephosphinidynephosphoranylphosphoranylidenephosphoranylidynephosphinylphosphinothioylphosphinimylphosphinylidenephosphinothioylidene phosphinylidynephosphophosphorosodiphosphinyldiphosphinylidene silylsilylenesilylidynedisilanyl1-disiloxanylsilyloxy(disilanyloxy)(disiloxanyloxy)(disilazanyloxy)disiloxanylidene-

N N H N H N
phosphorus H2PHP= P H4PH3P= H2P H2(O=)PH2(S=)PH2(HN=)PH(O=)P= H(S=)P= (O=)P (O=)2PO=PH2P-PHH2P-P= H3SiH2Si= HSi H3Si-SiH2H3Si-O-SiH2H3SiOH3Si-SiH2OH3Si-O-SiH2-OH3Si-NH-SiH2-OH3Si-O-SiH=

silicon

31

Examples :
formula inverted name uninverted name Diazene, 1,2-diphenyl1,2-diphenyldiazene

Ph-N=N-Ph

HO

N N

Phenol, 4-(phenyldiazenyl)4-(phenyldiazenyl)phenol

CH3-HN-N=N-NH-CH3 (CH3CH2CH2CH2)3P CH3HP-P(CH3)-P(CH3)-PHCH3 H-P=O

2-Tetrazene, 1,4-dimethyl1,4-dimethyl-2-tetrazene Phosphine, tributyltributylphosphine Tetraphosphine, 1,2,3,4-tetramethyl1,2,3,4-tetramethyltetraphosphine Phosphine, oxooxophosphine

O N P N
H2P-CH2-CH2-CH2-NH2 CH3CH2CH2CH2-N=PH3 4-CH3-CH2-O-PH(=O)-Ph-C(=O)OH (CH3O)2-P(=O)-CH2-C(=O)OH

Phosphineoxide, tris(1-aziridinyl)tris(1-aziridinyl)phosphineoxide

1-Propanamine, 3-phosphino3-phosphino-1-propanamine 1-Butanamine, N-phosphoranylideneN-phosphoranylidene-1-butanamine Benzoic acid , (4-ethoxyphosphinyl)(4-ethoxyphosphinyl)benzoic acid Acetic acid , (dimethoxyphosphinyl)(dimethoxyphosphinyl)acetic acid

H3Si-SiHCl-SiHCl-SiH3 H3Si-SiHF-SiHF-SiH2OH HOH2Si-(SiH2)3-SiH2OH H3Si-O-SiH2-S-SiH3

Tetrasilane, 2,3-dichloro2,3-dichlorotetrasilane 1-Tetrasilanol, 2,3-difluoro2,3-difluorotetrasilanol 1,5-Pentasilanediol Disiloxane, (silylthio)(silylthio)disiloxane

O CF3 C N

Si(CH3 )3 Si(CH3 )3
Acetamide, 2,2,2-trifluoro-N,N-bis(trimethylsilyl)2,2,2-trifluoro-N,N-bis(trimethylsilyl)acetamide

32

2.2.2 Monocyclic rings Monocyclic rings with at least ten ring atoms (with exception of silicon compounds and compounds with cumulated double bonds) are named according to the Hantzsch-Widman-method. Monovalent radicals take the suffix yl instead of e, except.: thienyl . For bivalent radicals the suffix ylidene is used. Closed anhydrides, cyclic imides, lactones and lactams also are treated as heterocyclic systems. Table 2.8. Suffixes for heterocyclic systems according to Hantzsch-Widman Number of members in the ring 3 4 5 6 7 8 9 10 Rings containing nitrogen Rings containing no nitrogen

unsaturated (1) -irine -ete -ole -ine (2) -epine -ocine -onine -ecine

saturated -iridine -etidine -olidine

(1)

unsaturated (1) -irene -ete -ole -in (2) -epin -ocin -onin -ecin

saturated -irane -etane -olane -ane (3) -epane -ocane -onane -ecane

The names of heterocyclic compounds with one ring ( except for silicon ) are composed by combining the prefix(es) from table 2.5 ( a is omitted if followed by a vowel) with one of the suffixes of table 2.8. Atoms with a higher position (= higher priority) in table 2.5 are named in the first place. Numbering starts with the prefix of highest priority and the remaining heteroatoms take a locant as low as possible. (1) (2) (3) If unsaturation is not maximal, the prefixes dihydro, tetrahydro,... are used. except. : phosphorin (e), arsenin (e) Phosphorus takes -inane H H HP P P N O O N HP P P
oxirane aziridine oxetane azetidine tetraphosphete

PH PH

tetraphosphetane

O S
1,3-oxathiolane
4

O N2 N
1,2,4-oxadiazole

PH H2C

PH

PH PH
tetraphospholane phosphorin phosphorinane

33

N N N

H N

H N2

N
2

S
1,3,5-triazine 1,4-oxathiin 1H-azepine 1H-1,2-diazepine azocine

O
O O
O N H
2,5-pyrrolidinedione

H N

O
2-oxetanone

O
hexahydro-2H-azepine-2-one

2,7-oxepanedione

Monocyclic rings with more than ten ring atoms, rings with cumulated double bonds and rings containing carbon and silicon are treated according to the replacement nomenclature.
O O

H N 11
1 4

H N N H
silacyclobutane

N8 H

SiH2

Si

1,4,7,10-tetraoxacyclododecane

1,4,8,11-tetrazacyclotetradecane

silabenzene

Silicon rings without carbon atoms are treated as their corresponding chain, prefixed by cyclo.
SiH2 SiH2
1

H2 Si H2 Si

SiH2 SiH2

H2 Si O

SiH2 O

HN H2Si

SiH2 NH

SiH2

cyclohexasilane

cyclotrisiloxane

cyclodisilazane

Table 2.9. Retained trivial names of the most important monocyclic heterocyclic compounds [8] .

0
5

S
5 2

furan (furanyl-)
H N

thiophene (thienyl-)

H N

1H-pyrrole or 2H-, 3HO

5

pyrrolidine
O

oxazole

isoxazole

34

S N

S N

thiazole
H N

isothiazole

H N N

1H-imidazole

or 2H-, 4H-

NH

imidazolidine

H N N
2

H N NH

1H-pyrazole

or 3H-, 4H-

pyrazolidine
H N

pyridine
H N

piperidine

N N

pyrazine
N N

N H

piperazine

pyrimidine
1

pyridazine
O N H

2H-pyran

or 4H-

morpholine

35

2.2.3 Polycyclic heterocyclic systems Fused ring systems The preferred ring becomes basic component and obtains a letter indication. the other ring gets suffix 'o and a number indication ( section 2.1.2 ) :
examples: oxepino, pyrrolo, pyrano, indolo, phosphorino... but: benzo, furo, thieno, pyrido, pyrimido, imidazo, quino, ...

Such names are valid for the most unsaturated compound, with or without an indicated hydrogen. Compounds which are not maximal unsaturated receive the prefix di, tetra, hexa, octa, deca, ...hydro- preceded by an indication of the position of saturation. The molecule is drawed in such a way that a maximal number of rings is placed on a horizontal line and a maximal number of rings appears in the right-up quadrant. Numbering starts clockwise with the atom next to the bridgehead extremely at the right side. Take further the following guidelines (arranged in descending precedence) into consideration: - The locant of the heteroatoms is as low as possible. - Priority according to table 2.5 has to be respected. - Carbon atoms in the fused bond get a locant as low as possible. - The indicated hydrogen is numbered as low as possible, on condition that substituents or favoured places are absent. - A heteroatom in an fused bond is prior to a heteroatom of a non-fused bond. When a hetero atom is shared by two (or more) rings, it is named in both (all) the components.
10 9 1

N N
7 6 5 4

N
3

N
7

N
4

N N
3

7,8,9,10-tetrahydropyrido[1,2-a][1,4]diazepine

tetrazolo[1,5-d][1,4]diazocine

[1,4] : brackets when the enclosed locants are not applicable to the total ringsystem after fusion.

Concerning the priority, following criteria are applied in the right order:

heterocyclic ring
7 7a
1

O
1a 3 2

O
dibenzo[b,e][1,4]dioxin

naphth[2,3-b]oxirene

36

- ring with heteroatom of highest precedence : N > O > S > P > Si

1

O
6

S O S

2 3

S
thieno[3,2-b]furan

1,4-dithiino[2,3-c]furan

- ring system with the greatest number of rings

1

H N
1

N
N5
4

N3

N
6

pyrido[2,3-g]quinoline

1H-pyrimido[5,4-b]indole

- ring system containing the largest individual ring

1
7 1

N N
5 6 4

O
2 3

O O3

O
4

pyrimido[1,2-a]azepine

1,3-dioxolo[4,5-b][1,4]dioxin

- ring system containing the greatest total number of heteroatoms

1
1

O O
4

N
3

N
4

furo[2,3-d]-1,3-dioxole

pyrido[2,3-e]1,2,4oxathiazine

- ring system containing the greatest variety of heteroatoms

7 1

N N
4

S
2

H N
2

O N
4

imidazo[2,1-b]thiazole

1H-pyrazolo[4,3-d]oxazole

- ring system containing the greatest number of heteroatoms of highest precedence.

7 1

N S
5 4

O N
3

thiazolo[5,4-f]benzoxazole

37

- ring system with the most linear structure.

2 1

N
8 7

c
6

1H-benz[k l]acridine

benzene fused on acridine

- ring system with the lowest locants for heteroatoms before fusion.
1 7

N N

N
4

pyrazino[2,3-d]pyridazine

A benzenoid ring fused with a monocyclic (Hantzsch-Widman) hetero ring: prefix 'benzo' and number indication for the heteroatoms in front of it:
1 2
9 1 2

O O

S
4

3-benzoxepin

2,4,3-benzodioxathiepin

Table 2.10. Retained trivial names for frequently used heterocyclic ringsystems [9]
O
1
6 1

6 5

2
5

benzofuran
1 6

isobenzofuran

6 5

H N
2 3

NH
5

1H-indole

2H-isoindole
1

H N N
2 3

7 2 6

indazole
N

N
4 3

indolizine

7 6

2 3

quinoline

isoquinoline
7 6

N N

2 3

cinnoline 38

phthalazine

N N

quinoxaline

quinazoline

1,8-naphthyridine
and isomers 1,5- 1,6- 1,7- 2,6- 2,7- naphthyridine
7 1

8 7

N
5 4

2H-quinolizine *
2

7 6

N N

N N

N
4

1H-pyrrolizine
H N N
7 8
7 6

pteridine
1 2 3

6 5 1 2 3

N N
4

purine *

N
10

acridine

8 7

H N

1
1

4
2 3

9H-carbazole *

N
9

phenanthridine
1 2

HN

N N

1H-perimidine *
8 5
1 10

phenazine

N
4

10

N
5

1,10-phenanthroline

and isomers 1,7- 1,8- 1,9- 2,7- 2,8- 2,9phenanthroline

10
8 7 8 6 7 5 9 1 2

anthyridine
S O

8 7

2 3

O
10

3 4

1H-xanthene
2

*
8 8 7 7

phenoxathiin
2

N O5

N S5

1H-phenothiazine

1H-phenoxazine *

* Place of indicated H is shown

39

2.2.4 Heterocyclic bridged structures Nomenclature: see alicyclic rings with bridges section 2.1.5; by further choice, the heteroatoms get the lowest locants in accordance with table 2.5 (replacement nomenclature).
1

2
6 7 5 4

1
2

N
4

O
3

O
5

7-oxabicyclo[2.2.1]heptane

6-oxabicyclo[3.1.0]hexane

2-azabicyclo[2.2.1]hept-5-ene-3-one

Bicyclocompounds containing rings with at least five atoms and a bridge of zero atoms are treated as fused compounds. Compare :
2 1 8 7
2

O O
6

O O
5

3 4

2
7

2,5,7,8-tetraoxabicyclo[4.2.0]octane

hexahydrofuro[2,3-b]furan

7-oxa-2-azabicyclo[4.2.0]octa-1,3,5-triene

2.2.5. Fused heterocyclic rings with bridges Table 2.11. Bridges with heteroatoms.( see also section 2.1.5 table 2.4 )
Examples : -O- : epoxy -O-O- : epidioxy -O-CH2- : (epoxymethano) -O-CH2-O- : (epoxymethoxy) -S- : epithio -O-S-O- : (epoxythioxy) -N< : nitrilo -NH- : imino -N=N- : diazeno -NH-NH- : biimino -NH-CH2- : (iminomethano) -NH-CH2-CH2- : (iminoethano) -SiH2- : silano
O

: 3,4-furano

( heteroatom is named first )

1
7 1

1 8a

NH

NH
9

4a
4

4,7-epoxyisobenzofuran

1,5-imino-3-benzazocine

8a,4a-(iminoethano)naphthalene

40

2.2.6 Heterocyclic spiro compounds Nomenclature: see section 2.1.5; if a further choice is possible, the heteroatoms take a locant as low as possible in accordance with table 2.5 (replacement nomenclature).
7 8 6 5 3 9 10 4 1
1

O H N8
5

O
4

1-oxaspiro[4.5]decane
5 1 3

1,4-dioxa-8-azaspiro[4.5]decane
1

H2Si H2Si
4

SiH2 SiH2
2

Si

SiH2 O O SiH2 9 O Si 6 O SiH2 O O SiH2

7 5

spiropentasilane

spiro[5.5]pentasiloxane
1

6 7 4

1 2 5'

O O

1'

O
4' 3 3'

3'

O
1'

7'

spiro[bicyclo[2.2.1]heptane-2,5-[1,3]dioxane]

3,3(2H,2H)-spirobibenzofuran

2.2.7 Connected identical heterocyclic rings The name of the connected ring is formed by putting the prefix : bi, ter, in front of the name of the component ring ( section 2.1.6 ) .
O
1'

N
N N
1

N N

O
2,2'-bifuran 4,4'-bipyridine

2,2-bi-2H-imidazole

41

3
Principal rules for the determination of skeletons in relation to the parent name
3.1 The skeleton with the functional group with the highest precedence forms the parent name. In general: the skeleton with the highest number of these principal function forms the parent name. Ph-C(=O)CH3 : 1-phenylethanone
O C CH3

1-(2-cyclohexene-1-yl)ethanone

4-H3C(O=)C-Ph-C(=O)OH : 4-acetylbenzoic acid

OH HO CH CH CH2 CH3

1-(4-hydroxyphenyl)-1,2-butanediol
OH

O CH3 C CH

O C O CH3

3-(2-oxocyclopentyl)-2,4-pentanedione

3.2 The parent name is determined by the sketeton with the principal function on a hetero atom in sequence N >P>O >S.
O HO C O NH NH C OH

2-(4-carboxyphenyl)hydrazine-1-carboxylic acid

Silanes are ranked between cyclic carbon parents and acyclic carbon parents.[10]
O CH3 Si

(methyloxosilyl)benzene

3.3

If the number of principal functions is the same for a chain and a ring system, then the cyclic system with the principal suffix forms the parent name, taking the conjunctive names in account (see chapter 6).
O C OH CH O CH C OH

O CH2 C CH2CH2CH3 O

2-(2-carboxyethenyl)benzoic acid

2-(2-oxopentyl)cyclopentanone 42

CH

ethynylbenzene

NH

(CH2)6 CH3

N-heptylcyclohexanamine

3.4

The priority in cyclic systems is based on the following criteria applied in the right order.

3.4.1 Nitrogenous heterocycle

N

4-(2-furanyl)pyridine

3.4.2 Heterocyclic ring 2-phenyloxetane

O

3.4.3 Ring system containing the largest number of rings 3.4.4 Spiro compounds > bridged fused > bridged > fused ring systems 3.4.5 Fused carbocycle with largest individual ring 3.4.6 Greatest number of ring atoms 3.4.7 Greatest number of ring atoms common to two or more rings 3.4.8 Lowest locants for bridges 3.4.9 Largest number of heteroatoms 3.4.10 Priority of heteroatoms other than nitrogen according O > S > P > Si 3.4.11 Most linear arrangement of rings 3.4.12 Lowest locants for heteroatoms 3.4.13 Most unsaturated ring
O HO C O C OH

cyclohexylbenzene
3.4.14 Lowest locants for indicated hydrogen

4-(4-carboxycyclohexyl)benzoic acid

43

3.5

The skeleton with the highest number of acyclic heteroatoms has priority.
CH2 CH2 CH3 CH3 O CH O CH2 O CH2 O CH2 O CH3

3-propyl-2,4,6,8,10-pentaoxaundecane 3.6 The skeleton with the greatest parent name is prior, for carbon chains the chain with the highest number of C atoms. CH3CH2CH(CH3)-CH2CH2OH : 3-methyl-1-pentanol CH3CH2CH2CH(CH2CH2CH3)CH=CH2 : 4-ethenylheptane
3.7 The skeleton with the greatest number of preferred acyclic heteroatoms according O > S > N > P > Si is prior.

3.8

The skeleton with the greatest number of multiple bonds has priority. CH2=CH-CH(CH2CH3)-CH=CH2 : 3-ethyl-1,4-pentadiene If the number of multiple bonds is equal, then the double bond precedes the triple bond . CH2=CH-CH(C CH)-CH=CH2 : 3-ethynyl-1,4-pentadiene

3.9
3.9.1 3.9.2 3.9.3 3.9.4

The skeleton with the lowest locants precedes.

Lowest locants for heteroatoms Lowest locants for suffixes Lowest locants for multiple bonds Lowest locants for double bonds, double bonds precede triple bonds

3.10 The most central parent name takes priority.

3.11 The parent name with the highest number of substituents has priority.
CH3 ClH2C C CH2Cl CH2Cl

1,3-dichloro-2-(chloromethyl)-2-methyl-propane

3.12 The parent name with the lowest locants for the substituents takes priority. 3.13 Multiplicative names have priority 3.14 The alphabetic lowest name has priority

44

4
Rules for substituents and numbering
4.1 Substituents, together with their locants, are indicated as prefixes to the parent name. They are placed in alphabetic order. The alphabetic value of a multiplicative prefix is only taken into account for composed substituents. If both occur on the same substituent, italic Roman letters are placed in front of the Arabic numerals. Ph-C(=O)-CH2-C(=O)-CF3 : 4,4,4-trifluoro-1-phenyl-1,3-butanedione CH3-NH-CH2-CH2-CH(CH3)-CH3 : N,3-dimethyl-1-butanamine CH3CH2CH2CH(CH2CH3)-C(CH3)2-CH2CH3 : 4-ethyl-3,3-dimethylheptane
Br
C(=O)Cl NO 2

CH3O

F
CF 3

1-bromo-3-fluoro-5-methoxybenzene

2-nitro-4-(trifluoromethyl)benzoylchloride

4.2

Numbering is determined by the suffix of the parent name, which itself takes the lowest number. CH2=CH-CH2CH2-C(=O)-CH3 : 5-hexene-2-one CH2=CH-C(=O)OH : 2-propenoic acid CH2=CH-CH2-NH2 : 2-propene-1-amine H2C=C(CH3)-C(=O)H : 2-methyl-2-propenal CH3-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-O-CH2-CH2-C(=O)OH : 4,6,9,12-tetraoxatetradecanoic acid

4.3 If there is no suffix, the numeration is determined by the unsaturation, which itself takes the lowest number. ClCH2CH2CH=CH2 : 4-chloro-1-butene CH3CH2CH=CH-CH=CH2 : 1,3-hexadiene (CH3)3C-CH=CH2 : 3,3-dimethyl-1-butene CH3-CH=CH-C CH : 3-pentene-1-yne CH2=CH-CH2-C CH : 1-pentene-4-yne

45

4.4 In most of the ring systems numeration is fixed.

N N

4-nitropyrimidine
NO 2

CH 3
2 1 7

2-methyl-bicyclo[3.1.1]hept-2-ene

O H C N8
5

1,4-dioxa-8-azaspiro[4.5]decane-8-carboxaldehyde
O
4

4.5 If the numbering is not determined by the parent name, counting starts at this end which delivers the lowest number for the substituent. In case of several substituents, numbering starts at this end for which the sum of the numbers are minimal. CH3CH2CH(CH3)CH2CH2CH3 3-methylhexane CH3-CH=CH-CH2Cl 1-chloro-2-butene CH3CH2CH2CHF-C(CH3)2-CH2CH3 4-fluoro-3,3-dimethylheptane 4.6 Substituents of the same kind are indicated by multiplicative prefixes di(2), tri(3), tetra(4), penta(5) ... ( priority for the choice of the parent name: the suffixes carboxylic acid, carboxaldehyde ...are used if the chain contains more than two such identical substituents). Cl2CH-C(=O)OH ClCH=CCl2
CH2C(=O )OH HO C C(=O)O H

dichloroacetic acid trichloroethene

2-hydroxy-1,2,3-propanetricarboxylic acid

CH2C(=O )OH

Prefixes bis-, tris-, tetrakis, pentakis, ... are used to indicate composed substituents.
Cl

HOH2C C HOH2C

CH2OH CH2OH
Cl C

O CH2 C OH

2,2-bis(hydroxymethyl)-1,3-propanediol

Cl 3,3,3-tris(4-chlorophenyl)propanoic acid

4.7

Parentheses are placed around (component substituent radicals) and brackets enclose [complex substituent radicals] to avoid confusion.
O ClCH2 O CH2CH2CH3

CH3 CH3 N CH2CH2 O

S C NH2

C NH C O

(chloroacetyl)carbamic acid propyl ester propyl (chloroacetyl)carbamate

4-[2-(dimethylamino)ethoxy]benzenecarbothioamide

46

5
Names with multiple identical heading parents
If the name of a compound consists of multiple identical parent names in symmetrical positions then the multiplicative nomenclature is used and a multiplying radical is employed. For heading parents attached to the same atom, a specific name for the multiplying radical, equal or similar to the corresponding prefix, is used. When the heading parents are attached to a radical consisting of several atoms, usually the suffix diyl, triyl, is used if no specific radical name is available. In the uninverted name, brackets are placed around the [parent name]. Table 5.1. Examples of multiplying radicals.[10] Multiplying radical
-CH2>CH=C= -CH(CH3)CH3-C CH3CH2-C -CH2CH2-CH=CH-CH2-CH=CH-CC>CH-CH< -CH2-CH< -CH2-CH2-CH<

Name

Multiplying radical
-S-S-S-

Name

methylene methylidyne methanetetrayl ethylidene ethylidyne propylidyne 1,2-ethanediyl 1-propene-1,3-diyl 1,2-ethenediyl 1,2-ethynediyl 1,2-ethanediylidene 1-ethanyl-2-ylidene 1-propanyl-3-ylidene 1,2,3-propanetriyl 1,2-cyclopropanediyl

thio dithio

-S(=O)sulfinyl -S(=O)2sulfonyl -S(=O)2-S(=O)2- disulfonyl -N< -NH-N=N>N-N< -NH-NH-N(=O)=N-N=N-NH-(NH)4-HP-P< -HP-PH-P=P=P-P= nitrilo imino 1,2-diazenediyl previous azo 1,2-hydrazinediylidene prev azino 1,2-hydrazinediyl previous hydrazo 1-oxido-1,2-diazenediyl prev azoxy 1-triazene-1,3-diyl 1,4-tetrazanediyl phosphinidene phosphinidyne 1,2-diphosphinediyl 1,2-diphosphenediyl 1,2-diphosphinediylidene

CH2 CH CH2

-C6H4-C6H3< -(C10H6)N

isomers of phenylene isomers of benzenetriyl isomers of naphthalenediyl

2,6-pyridinediyl

-P(=O)(OH)phosphinico -P(=O)(OCH3)- methoxyphosphinylidene -P(=S)(OCH3)- methoxyphosphinothioylidene

-C(=O)-C(=O)-C(=O)-C(=O)-C C-C(=O)-O-C(=O)-O-C(=S)-C(=NH)-O-O-O-O-CH2-O-O-CH2-CH2-O-

carbonyl (1,2-dioxo-1,2-ethanediyl) -SiH2silylene (1,4-dioxo-2-butyne-1,4-diyl) -HSi< silylidyne [carbonylbis(oxy)] >Si< silanetetrayl -H2Si-SiH21,2-disilanediyl carbonothioyl -H2Si-NH-SiH2- 1,3-disilazanediyl carbonimidoyl -H2Si-O-SiH21,3-disiloxanediyl oxy H2Si O SiH O SiH2 dioxy [methylenebis(oxy)] 1,3,5-trisiloxanetriyl [1,2-ethanediylbis(oxy)]

47

Retained names : Some peroxides, trioxides, and also some disulfides, trisulfides, and their oxides are treated according to the radicofunctional nomenclature, insofar they are not subjected to the replacement nomenclature : di(cyclo)alkyl, di(substit.)phenyl, diacetyl, dibenzoyl, Their heading parent is: peroxide, disulfide,

CH3CH2CH2-O-CH2CH2CH3 : 1,1'-oxybis[propane] Ph-SO2-Ph : sulfonylbis[benzene] HOCH2-CH2-NH-CH2-CH2OH : 2,2'iminobis[ethanol]

O

CH3 HO C CH3
4,4(1-methylethylidene)bis[phenol]

CH3 CH3

OH
C O 1,1-(1,2-phenylene)bis[ethanone]

O C OH O HO C CH2 H2 C P O
Cl

CH2 C OH

H2Si SiH2

Cl

2,2,2-phosphinidynetris[acetic acid]

1,2-disilanediylbis[4-chlorobenzene]

O O O C

3,3-dithiobis[pyridine]

dibenzoyl peroxide

CH3
S S

CH3 O C CH3 CH3

H3C

CH3
diphenyl disulfide

bis(1,1-dimethylethyl) peroxide

48

6
Nomenclature with conjunctive parent compound names
When a ring system is attached by single bonds to one ore more saturated acyclic hydrocarbon chains, each of which bearing only one terminal functional group with priority as a suffix ( thus ketones exclusive ), the conjunctive nomenclature is used. The locants for the substituents on the chain are marked with Greek letters beginning with for the position next to the functional group. Roman letters, Greek letters, Arabic numerals make the sequence of the locants. As opposed to the rule 3.3 for the priority of the parent name in the substitutive nomenclature, the conjunctive nomenclature is preferred when the functional group is present on the ring as well as on the chain in the same number.
N CH2 CH2NH2
3-pyridineethanamine

O CH2 CH2 C H
benzenepropanal

H O C C OH

CH3 -methylbenzeneacetic acid

CH2OH CH2CH2OH
2-(hydroxymethyl)-benzeneethanol
HO CH2 OH

CH3
N,

CH2 CH CH3

NH

CH3

4-hydroxybenzenemethanol

trimethylbenzeneethanamine

C C H

CH OH

CH2C(=O)OH CH2C(=O)OH
2,3-naphthalenediacetic acid

-ethynylcyclohexanemethanol

O HO C

O CH2CH2 C OCH3

4-carboxybenzenepropanoic acid 1-methyl ester

49

References

[1]

Chemical Abstracts Index Guide 2002, 2004 published by the American Chemical Society Chemical Abstracts Index Guide 2002 Appendix IV Chemical Abstracts Index Guide 2002 Appendix IV 185 Chemical Abstracts Chemical Substance Index Chemical Abstracts Index of Ring Systems Eleventh Collective Index 1982-1986 Chemical Abstracts Parent Compound Handbook 1976, supplement 1983 Chemical Abstracts Index Guide 2002 Appendix IV 148 table IV Chemical Abstracts Index Guide 2002 Appendix IV 146 table III Chemical Abstracts Index Guide 2002 Appendix IV 149 table V

[2] [3] [4] [5] [6] [7] [8] [9]

[10] Nomenclature changes for CA index names 2007: www.cas.org/

50