Bünzli-Trepp U. Systematic Nomenclature of Organic, Organometallic and Coordination Chemistry

Berlin: Logos Verlag, 2021. 696 p.Accuracy and unambiguity are at the heart of good science communication, and the publication of the second edition of Ursula Bünzli-Trepp’s book on chemical nomenclature is a significant contribution toward achieving these standards. The title of the book is self-explanatory, and the author presents the topic in an encyclopedic manner. The book comprises six chapters: Directions for the use of this book, Fundamentals, Guide to name construction and name interpretation, Molecular-skeleton parents, Substituent prefixes, and Compound classes, together with appendices and tables. The coverage of organic compounds is more comprehensive than that of coordination and organometallic species, which is confined to 55 pages in the chapter entitled Compound classes. The text is an overview of the major nomenclature systems used in the Anglophone world but cannot be considered a complete guide to any of them. The liberal approach to nomenclature found in the primary literature is a justification for a book that shows what could (and could not) be considered an appropriate name.
The text usually emphasizes the differences between IUPAC and Chemical Abstracts Service (CAS) nomenclatures and occasionally gives value judgements of the approaches (see below on anionic ligands). Very often, the author lands on the side of the CAS name. Much of the book comprises loose paraphrases of IUPAC and CAS documents, making it a good reference work but does not necessarily enhance the readability. The organization of the sections might not be obvious to all readers, and it is not always simple to determine the hierarchical level of nomenclature to which a particular section belongs.Directions for Use of the Book
Fundamentals
Nomenclature terms and definitions used in the Book
Conventions for enclosing marks and vowels in names
Enclosing marks
Vowels
Guide to Name Construction and Name Interpretation
General procedure and choice of the senior compound class (choice of the principal group)
Nomenclature types
Substitutive nomenclature
Conjunctive nomenclature
Multiplicative nomenclature: compounds with identical structural units
Additive nomenclature
Subtractive nomenclature
Functional-class nomenclature
Determination of the molecular-skeleton parent
Numbering of the molecular-skeleton parent and of other structure components
Alphabetical order of prefixes or parent-substituent names
Molecular-Skeleton Parents
Preliminary notes
Hydrocarbon chains
Heterochains
Preliminary notes
Heterochains with irregularly placed heteroatoms: replacement nomenclature ('a' nomenclature)
Heterochains with regularly placed heteroatoms: homogeneous and heterogeneous heterochains
Carbomonocycles
Heteromonocycles
Preliminary notes
Heteromonocycles with compulsory trivial names
Heteromonocycles with ten or fewer ring members: extended Hantzsch–Widman nomenclature
Heteromonocycles with more than ten ring members: replacement nomenclature ('a' nomenclature)
Silicon-containing heteromonocycles
Fused polycycles (carbo- and heterocycles)
Preliminary notes
Fused polycycles with compulsory semitrivial or trivial names
Fused polycycles consisting of a parent component and attached components: fusion names: fusion names
Fused polycycles with replacement names ('a' names)
von Baeyer bridged polycycles (carbo- and heterocycles)
Bridged fused polycycles (carbo- and heterocycles)
Spiropolycycles (carbo- and heterocycles)
Preliminary notes
Spiropolycycles with carbomonocycle or heteromonocycle components
Spiropolycycles with at least one fusedpolycycle component or one von Baeyer bridged-polycycle component
Ring assemblies of identical ring components (carbo- and heterocycles)
Substituent Prefixes
Preliminary notes
Prefixes of mononuclear substituents
Prefixes of hydrocarbon-chain substituents
Prefixes of heterochain substituents
Prefixes of carbocycle substituents
Prefixes of heterocycle substituents
Prefixes of ring-assembly substituents
Prefixes of composite substituents: choice of the parent substituent
Prefixes of carbonyl-containing substituents and analogs
Compound Classes
Preliminary notes
Radicals
Preliminary notes
Radical center at a molecular-skeletal parent
Radical center at a characteristic group
Polyradicals
Cations
Preliminary notes
Cation center by the formal addition of electrophiles E+
Cation center by the formal removal of hydride ions H–
Cation center resulting from skeletal bonding of a heteroatom
Cation center in spiropolycycles
Cation substituents (prefixes)
Polycations
Anions
Preliminary notes
Anion center by the formal removal of protons H+
Anion center by the formal addition of hydride ions H–
Anion substituents (prefixes)
Polyanions
Zwitterions
Radical ions
Carboxylic, carbothioic, carboselenoic, carbotelluroic, carbohydrazonic, carboximidic, and corresponding carboperoxoic acids and salts
Preliminary notes
Carboxylic acids
Carbothioic, carboselenoic, carbotelluroic, carbohydrazonic, and carboximidic acids
Carboperoxoic acids (peroxy acids) and their chalcogeno, hydrazono, and imido replacement analogs
Salts of carboxylic acids and of their chalcogeno, hydrazono, imido, and peroxy replacement analogs
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
C-Oxoacids: carbonic and formic acid and their replacement analogs and corresponding salts
S-, Se-, Te-, and N-Oxoacids
P- and As-Oxoacids
Sb-, Bi-, Si-, and B-Oxoacids
Anhydrides
Esters and lactones
Acid halides
Amides, lactams, cyclic imides, and amidines
Hydrazides
Nitriles
Aldehydes and their oxime and hydrazone derivatives
Ketones and their oxime and hydrazone derivatives
Alcohols and phenols
Hydroperoxides
Amines
Imines
Nitrogen compounds
Phosphorus and arsenic compounds
Antimony and bismuth compounds
Boron compounds
Silicon, germanium, tin, and lead compounds
Oxygen compounds
Sulfur, selenium, and tellurium compounds
Carbon compounds
Halogen compounds
Organometallic and coordination compounds
Appendixes
Specialist nomenclatures
Preliminary notes
Alkaloids
Amino acids and peptides
Carbohydrates
Cyclitols
Nucleosides, nucleotides, and nucleic acids
Steroids
Terpenes, carotenoids, and retinoids
Vitamins
Porphyrins and bile pigments
Polymers
References for specific compound classes, Internet addresses, and nomenclature software
Multiplying affixes
Modifying syllables
Heteroatom syllables and element names
Indicated H atom 'H ' (indicated hydrogen) and tautomers
Configuration descriptors in names
Definitions
The CIP system for the specification of the configuration of a stereogenic center, axis or plane, or double bond
Stereodescriptors for the denotation of the absolute and relative configuration in names
Configuration of organometallic and coordination compounds
Lambda (λ) convention
Isotopically modified compounds
Preliminary notes
Isotopically modified compounds: IUPAC Recommendations
Isotopically modified compounds: CA Guidelines
List of substituent prefixes
Index