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Chemistry International
Vol. 24, No. 5
September 2002


Highlights from Pure and Applied Chemistry

Phane Nomenclature. Part II. Modification of the Degree of Hydrogenation and Substitution Derivatives of Phane Parent Hydrides (IUPAC Recommendations 2002)

by H. A. Favre, D. Hellwinkel, W. H. Powell, H. A. Smith, Jr., and S. S.-C. Tsay
Pure and Applied Chemistry, Vol. 74, No. 5, pp. 809-834 (2002)

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 structure can be modified by an operation called "amplification," a process that replaces one or more special atoms (superatoms) of the simplified skeleton by multiatomic structure(s).


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

Simplified skeletal name: heptaphane
Phane parent hydride name: 1(2)-pyridina-3,5(1,3),7(1)-tribenzenaheptaphane

The multiatomic structure is a fully saturated or mancude ring or ring system. A mancude ring or ring system contains the maximum number of noncumulative double bonds. In the amplification operation, each superatom is replaced by an amplificant denoted 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 those replaced by amplification prefixes are, by convention, 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 prefixes, such as "oxa," "aza," etc., that indicate replacement of a single atom, usually a carbon atom, by a different atom.

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 specified by the amplification prefixes that are linked to the adjacent normal atoms of the simplified parent skeleton.

In addition to the basic principles, rules and conventions of Phane Nomenclature, Part I [Pure Appl. Chem. 70(8), 1513-1545 (1998)] contains the fundamental methodology for numbering phane parent hydrides and the application of skeletal replacement ("a") nomenclature for naming heterophane parent hydrides.

Part II of Phane Nomenclature describes derivatives of phane systems formed by substitutive nomenclature. The following nomenclatural features are described: indicated and added hydrogen, order of seniority for numbering, substituents expressed as suffixes, substituents cited as prefixes, phane parent hydrides modified by addition or subtraction of hydrogen atoms, and polyfunctional derivatives.



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