Vol. 24, No. 5
from Pure and Applied Chemistry
Nomenclature. Part II. Modification of the Degree of Hydrogenation and
Substitution Derivatives of Phane Parent Hydrides (IUPAC Recommendations
A. Favre, D. Hellwinkel, W. H. Powell, H. A. Smith, Jr., and S. S.-C.
Pure and Applied
Chemistry, Vol. 74, No. 5, pp. 809-834 (2002)
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).
skeletal name: cycloheptaphane
Phane parent hydride name: 1(2,7)-naphthalena-4(1,3)-benzenacycloheptaphane
skeletal name: heptaphane
Phane parent hydride name: 1(2)-pyridina-3,5(1,3),7(1)-tribenzenaheptaphane
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.
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.
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.
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.