Substitutive nomenclature INDEX

Compounds containing the neutral (formally zwitterionic) group =N2 attached by one atom to carbon are named by adding the prefix diazo- to the name of the parent compound (Rule 931.4), e.g., diazomethane, ethyl diazoacetate. Diazo is a so-called characteristic group appearing only as a prefix in substitutive nomenclature. Chemical Abstracts and Beilstein indexing of diazo compounds is analogous to that mentioned above for diazonium ions and salts, but Diazo compounds is not... 

Current IUPAC and Chemical Abstracts nomenclature has been employed in this index with the former given preference. Substitutive nomenclature has been given preference over radicofunc-tional, additive, subtractive, conjunctive or replacement nomenclature, except where this becomes unwieldy. With many bicyclic and polycyclic compounds bearing heteroatoms, standard bicyclic or polycyclic oxa, aza, and thia replacement nomenclature has often been used. With certain functional groups, where the names are rather complex and probably not familiar to most organic chemists, such as ylides, those compounds have simply been named as sulfur, tellurium and arsonic ylides. Metal catbenes have been treated similarly. With more complex functionality and many heterocycles, the Beilstein Commander Crossfire nomenclature system has been used with certain modifications. 

To follow substitutive nomenclature logically for complex cases, new polyradical terminations are required. The need for them, as well as the resultant troubles in indexing, are arguments against substitutive nomenclature. On the other hand, additive nomenclature is against the fundamental principles—p-hydroxybenzoic acid is not correctly described as water-benzoic acid or phenol-p-formic acid. 

Tervalent organophosphorus compounds containing one single P-N bond with the valency of each atom saturated by protons or carbons (but no other heteroatoms) have been known since their discovery by MichaeUs more than one century ago [ 1 ] and named indistinctly as aminophosphanes, phosphanamines, phosphazanes, or phosphinous amides. This last chemical nomenclature is the one used by the Chemical Abstracts Service (CAS) for indexing these compounds and is also the one that best delimits the scope of this review those species derived from the parent H2P-NH2 (phosphinous amide in CAS nomenclature) by partial or total substitution of protons by hydrocarbon radicals (Table 1). 

As already pointed out, the nomenclature rules employed by Chemical Abstracts yield a unique index name for every structure, whereas the IUPAC Rules allow some latitude. This latitude is considerable with regard to the naming of substituted structures, and it is usually possible for an author to find in the rules a procedure suitable for any specific purpose. 

A word of caution should be added with respect to Chemical Abstracts, as far as chirality assignments of homoannular substituted ferrocene derivatives are concerned. Until the 8th collective index, only (-f) and (—) are found as chirality indicators. For quite a long time, no descriptors were given at all, only the remark stereoisomer , followed by the registry number, which does not allow identification of a compound easily. This fact is in sharp contrast to the claims of Chemical Abstracts Service authors that they would consequently use Schlogl s central descriptors [20, 21]. Since volume 114, the (R, S ) nomenclature for ferrocene derivatives begins to appear, but its application is not very consequent, at least at the time where the book was written, and it is advisible to examine the orginal article rather than trust Chemical Abstract s descriptors. 

The convenience of indexers is not a primary consideration for nomenclature development. Here is a conflict requiring resolution. The obvious step is to define the limits within which the additive and the substitutive principle are severally preferable, unless all indexers adopt a ciphering system where such problems do not arise and the field is left clear for cursive text. 

If a retrospective literature search is to be carried out back to the beginning of Chemical Abstracts, the searcher must be somewhat familiar with the nomenclature rules and substance names used at that time, as there was no Index Guide and no internal cross-references before 1946. Up to the fourth collective period (1946) the substitution positions were designated by letters ortho-, para-, meta-Y>os ons) (Fig. 60) rather than numbers. In addition, the abstract numbers were written in a different form at that time, e.g. the reference to Vol. 40 2189 in the fourth collective index. 

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