1 Directions for Use of the Book ............................... l
2 Fundamentals ................................................. 3
2.1 Nomenclature terms and definitions used in the Book ..... 3
2.2 Conventions for enclosing marks and vowels in names ..... 9
2.2.1 Enclosing marks .................................. 9
2.2.2 Vowels ........................................... 9
3 Guide to Name Construction and Name Interpretation .......... 13
3.1 General procedure and choice of the senior compound
class (choice of the principal group) .................. 13
3.2 Nomenclature types ..................................... 29
3.2.1 Substitutive nomenclature ....................... 29
3.2.2 Conjunctive nomenclature ........................ 30
3.2.3 Multiplicative nomenclature: compounds with
identical structural units ...................... 32
3.2.4 Additive nomenclature ........................... 36
3.2.5 Subtractive nomenclature ........................ 37
3.2.6 Functional-class nomenclature ................... 38
3.3 Determination of the molecular-skeleton parent ......... 41
3.4 Numbering of the molecular-skeleton parent and of
other structure components ............................. 49
3.5 Alphabetical order of prefixes or parent-substituent
names .................................................. 53
4 Molecular-Skeleton Parents .................................. 55
4.1 Preliminary notes ...................................... 55
4.2 Hydrocarbon chains ..................................... 55
4.3 Heterochains ........................................... 61
4.3.1 Preliminary notes ............................... 61
4.3.2 Heterochains with irregularly placed
heteroatoms: replacement nomenclature
('a'nomenclature) ............................... 61
4.3.3 Heterochains with regularly placed
heteroatoms: homogeneous and heterogeneous
heterochains .................................... 62
4.4 Carbomonocycles ........................................ 67
4.5 Heteromonocycles ....................................... 73
4.5.1 Preliminary notes ............................... 73
4.5.2 Heteromonocycles with compulsory trivial names .. 73
4.5.3 Heteromonocycles with ten or fewer ring
members: extended Hantzsch-Widman nomenclature .. 76
4.5.4 Heteromonocycles with more than ten ring
members: replacement nomenclature
('a'nomenclature) ............................... 81
4.5.5 Silicon-containing heteromonocycles ............. 82
4.6 Fused polycycles (carbo- and heterocycles) ............. 85
4.6.1 Preliminary notes ............................... 85
4.6.2 Fused polycycles with compulsory semitrivial
or trivial names ................................ 86
4.6.3 Fused polycycles consisting of a parent
component and attached components: fusion
names ........................................... 95
4.6.4 Fused polycycles with replacement names
('a'names) ..................................... 114
4.7 von Baeyer bridged polycycles (carbo- and
heterocycles) ......................................... 117
4.8 Bridged fused polycycles (carbo- and heterocycles) .... 123
4.9 Spiropolycycles (carbo-and heterocycles) .............. 133
4.9.1 Preliminary notes .............................. 133
4.9.2 Spiropolycycles with carbomonocycle or
heteromonocycle components ..................... 133
4.9.3 Spiropolycycles with at least one fused-
polycycle component or one von Baeyer
bridged-polycycle component .................... 135
4.10 Ring assemblies of identical ring components
(carbo- and heterocycles) ............................. 141
5 Substituent Prefixes ....................................... 145
5.1 Preliminary notes ..................................... 145
5.2 Prefixes of mononuclear substituents .................. 145
5.3 Prefixes of hydrocarbon-chain substituents ............ 146
5.4 Prefixes of heterochain substituents .................. 147
5.5 Prefixes of carbocycle substituents ................... 148
5.6 Prefixes of heterocycle substituents .................. 150
5.7 Prefixes of ring-assembly substituents ................ 152
5.8 Prefixes of composite substituents: choice of the
parent substituent .................................... 153
5.9 Prefixes of carbonyl-containing substituents and
analogs ............................................... 156
6 Compound Classes ........................................... 159
6.1 Preliminary notes ..................................... 159
6.2 Radicals .............................................. 161
6.2.1 Preliminary notes .............................. 161
6.2.2 Radical center at a molecular-skeletal parent .. 161
6.2.3 Radical center at a characteristic group ....... 163
6.2.4 Polyradicals ................................... 167
6.3 Cations ............................................... 169
6.3.1 Preliminary notes .............................. 169
6.3.2 Cation center by the formal addition of
electrophiles E+ ............................... 169
6.3.3 Cation center by the formal removal of
hydride ions H- ................................ 175
6.3.4 Cation center resulting from skeletal bonding
of a heteroatom ................................ 178
6.3.5 Cation center in spiropolycycles ............... 180
6.3.6 Cation substituents (prefixes) ................. 182
6.3.7 Polycations .................................... 184
6.4 Anions ................................................ 187
6.4.1 Preliminary notes .............................. 187
6.4.2 Anion center by the formal removal of
protons H+ ..................................... 188
6.4.3 Anion center by the formal addition of
hydride ions H- ................................ 193
6.4.4 Anion substituents (prefixes) .................. 193
6.4.5 Polyanions ..................................... 194
6.5 Zwitterions ........................................... 195
6.6 Radical ions .......................................... 199
6.7 Carboxylic, carbothioic, carboselenoic,
carbotelluroic, carbohydrazonic, carboximidic, and
corresponding carboperoxoic acids and salts ........... 203
6.7.1 Preliminary notes .............................. 203
6.7.2 Carboxylic acids ............................... 203
6.7.3 Carbothioic, carboselenoic, carbotelluroic,
carbohydrazonic, and carboximidic acids ........ 214
6.7.4 Carboperoxoic acids (peroxy acids) and their
chalcogeno, hydrazono, and imido replacement
analogs ........................................ 218
6.7.5 Salts of carboxylic acids and of their
chalcogeno, hydrazono, imido, and peroxy
replacement analogs ............................ 220
6.8 Sulfonic, sulfinic, and sulfenic acids, selenonic,
seleninic, and selenenic acids, telluronic,
tellurinic, and tellurenic acids, their chalcogeno,
hydrazono, imido, and peroxy replacement analogs,
and corresponding salts ............................... 223
6.9 C-Oxoacids: carbonic and formic acid and their
replacement analogs and corresponding salts ........... 229
6.10 S-,Se-,Te-,andN-Oxoacids .............................. 237
6.11 P-and As-Oxoacids ..................................... 243
6.12 Sb-,Bi-,Si-,and B-Oxoacids ............................ 253
6.13 Anhydrides ............................................ 257
6.14 Esters and lactones ................................... 267
6.15 Acid halides .......................................... 285
6.16 Amides, lactams, cyclic imides, and amidines .......... 295
6.17 Hydrazides ............................................ 313
6.18 Nitriles .............................................. 321
6.19 Aldehydes and their oxime and hydrazone derivatives ... 325
6.20 Ketones and their oxime and hydrazone derivatives ..... 333
6.21 Alcohols and phenols .................................. 347
6.22 Hydroperoxides ........................................ 355
6.23 Amines ................................................ 359
6.24 Imines ................................................ 367
6.25 Nitrogen compounds .................................... 371
6.26 Phosphorus and arsenic compounds ...................... 383
6.27 Antimony and bismuth compounds ........................ 391
6.28 Boron compounds ....................................... 397
6.29 Silicon, germanium, tin, and lead compounds ........... 403
6.30 Oxygen compounds ...................................... 409
6.31 Sulfur, selenium, and tellurium compounds ............. 415
6.32 Carbon compounds ...................................... 425
6.33 Halogen compounds ..................................... 429
6.34 Organometallic and coordination compounds ............. 433
Appendixes .................................................... 487
A.l Specialist nomenclatures ................................. 487
A.1.1 Preliminary notes ................................. 487
A.1.2 Alkaloids ......................................... 487
A.1.3 Amino acids and peptides .......................... 490
A.1.4 Carbohydrates ..................................... 494
A.1.5 Cyclitols ......................................... 509
A.1.6 Nucleosides, nucleotides, and nucleic acids ....... 510
A.1.7 Steroids .......................................... 516
A.1.8 Terpenes, carotenoids, and retinoids .............. 520
A.1.9 Vitamins .......................................... 526
A.1.10 Porphyrins and bile pigments ...................... 529
A.1.11 Polymers .......................................... 531
A.1.12 References for specific compound classes,
Internet addresses, and nomenclature software ..... 536
A.2 Multiplying affixes ...................................... 539
A.3 Modifying syllables ...................................... 541
A.4 Heteroatom syllables and element names ................... 543
A.5 Indicated H atom 'H'(indicated hydrogen) ................. 547
A.6 Configuration descriptors in names ....................... 557
A.6.1 Definitions ....................................... 557
A.6.2 The CIP system for the specification of the
configuration of a stereogenic center, axis or
plane, or double bond ............................. 559
A.6.3 Stereodescriptors for the denotation of the
absolute and relative configuration in names ...... 571
A.6.4 Configuration of organometallic and coordination
compounds ......................................... 582
A.7 Lambda (λ) convention .................................... 593
A.8 Isotopically modified compounds .......................... 599
A.8.1 Preliminary notes ................................. 599
A.8.2 Isotopically modified compounds: IUPAC
Recommendations ................................... 600
A.8.3 Isotopically modified compounds: CA Guidelines .... 601
Index ......................................................... 609
Tables
Tab.3.1 Substituents cited only as prefixes ................ 18
Tab.3.2 Compound classes and characteristic groups
(ending or prefix), listed in the order of
decreasing seniority for the choice of the
principal group .................................... 19
Tab.3.3 Prefixes of frequently occurring multivalent
linking substituents ............................... 34
Tab.4.1 Final syllables for Hantzsch-Widman names .......... 78
Tab.4.2 Fundamental fused carbopolycycles with
semitrivial or trivial names ....................... 89
Tab.4.3 Fundamental heterocycles with semitrivial or
trivial names: monocycles and fused polycycles ..... 91
Tab.4.4 Bridge names for bridged fused polycycles ......... 126
Tab.6.1 Acid halide suffixes for halides of carboxylic,
formic, sulfonic, sulfinic, and sulfenic acids
and analogs ....................................... 286
Tab.6.2 Amide suffixes and prefixes for amides of
carboxylic, formic, sulfonic, sulfinic, and
sulfenic acids and analogs ........................ 298
Tab.6.3 Compound classes for R-X with -X =-CN, -NC,
-OCN, etc., and -NCO, etc., and R = alkyl or
aryl .............................................. 321
Tab.6.4 Ligand abbreviations for use in formulas and
corresponding names ............................... 472
Tab.A.1 Multiplying affixes expressing the multiple
occurrence of a simple substituent or
modification, an unsaturation, a heteroatom,
a simple ligand, or a central atom. Numerical
syllables for the designation of a hydrocarbon
or 'a' name ....................................... 540
Tab.A.2 Heteroatom syllables or 'a' syllables, listed in
decreasing seniority order, as well as element
names and 'ate' names for organometallic and
coordination compounds, listed in increasing
seniority order ................................... 543
Tab.A.3 Polyhedral symbols ................................ 582
Tab.A.4 Frequently occurring nuclide symbols for the
designation of isotopically modified compounds .... 599
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