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 Pure Appl. Chem., Vol. 70, No. 8, pp. 1513-1545, 1998.




Phane Nomenclature.
Part I: Phane Parent Names

(Recommendations 1998)

W.H. Powell

World Wide Web version prepared by G. P. Moss

Synopsis: Phane nomenclature is a new method for building names for organic structures by assembling names that describe component parts of a complex structure. It is based on the idea that a relatively simple skeleton for a parent hydride can be modified by an operation called "amplification", a process that replaces one or more special atoms (superatoms) of a simplified skeleton by multiatomic structures. In this set of recommendations, multiatomic structures are fully saturated rings or ring systems or unsaturated rings or ring systems with the maximum number of noncumulative double bonds (mancude). In the amplification operation each superatom is replaced by a ring or ring system identified in the name by an "amplification prefix" attached to a stem called a "simplified skeletal name". The latter ends with the term "phane" and is formed according to the principles for deriving names of saturated hydrocarbons. Accordingly, all of the atoms implied by the skeletal name, except for the superatoms are, by convention, traditional saturated carbon atoms. An amplification prefix is derived from the name of the corresponding cyclic parent hydride by the addition of the terminal letter "a" with elision of a terminal vowel of the parent hydride name, if present. Phane prefixes thus resemble the traditional skeletal replacement ("a") prefixes, such as "oxa", "aza", etc., that indicate replacement of a single skeletal unit of structure, usually a carbon unit, by a different unit of structure.

Simplified skeletal name: cycloheptaphane
Phane parent hydride name: 1(2,7)-naphthalena-4(1,3)-benzenacycloheptaphane

The locants in front of the parentheses in the phane parent hydride name identify the positions of the superatoms in the simplified skeleton that are replaced by the ring structure specified by the amplification prefix immediately following. By the same token, they also identify the positions of the rings and ring systems in the phane parent hydride. These locants are determined by the inherent numbering of the simplified skeleton and the seniority of the rings and ring systems in the phane parent hydride. The locants within the parentheses specify the atoms of the ring structure expressed by the amplification prefixes that are linked to the adjacent normal atoms of the simplified parent skeleton.

In addition to the basic principles of phane nomenclature, Part I contains the fundamental methodology for numbering substituents and the application of skeletal replacement ("a") nomenclature for naming heterophane parent hydrides.

World Wide Web version prepared by G. P. Moss


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