Carbon as the pure element exists in several forms that are as different from one another as it is

possible to imagine. Different forms of a pure element are called allotropes. One allotrope of pure
carbon is the very soft and totally black substance called graphite, the main substance at the
center of pencils and the main component of charcoal and chimney soot. Another allotropic form
of carbon is diamond, the colorless brilliant gem that is the hardest of all substances found in
nature. Still another allotrope, perhaps the most exotic, is called buckminsterfullerene after the
inventor of the geodesic dome, Buckminster Fuller.
The different properties of these allotropic forms arise from different structural arrangements
of the carbon atoms in each form, and these arrangements result, in part, from different
ybridization states of their carbon atoms. The car- bon atoms of diamond are all sp3 hybridized
with tetrahedrally oriented bonds. The structure of diamond is what you would get if you
extended the structure of adamantane in three dimensions. The great hardness of diamond results
from the fact that the entire diamond crystal is one large moleculea network of interconnecting
rings that is held together by millions of strong covalent bonds.
In graphite the carbon atoms are sp2 hybridized. Because of the trigonal planar orientation of
their covalent bonds, the carbon atoms of graphite are in sheets. The sheets are actually huge
molecules consisting of fused benzene rings (see below). While all of the covalent bonds of each
sheet lie in the same plane, the sheets are piled one on another and the p orbitals of their benzene
rings keep them apart. Although these p orbitals interact, their interactions are very weak, much
weaker than those of covalent bonds, allowing the individual sheets to slide past one another and
accounting for graphites usefulness as a lubricant.
Buckminsterfullerene (shown on the next page) is a representative of a new class of carbon
compounds discovered in 1985 consisting of carbon clusters called fullerenes (see Section 14.8C
for the story of their discovery and synthesis). Buckminsterfullerene (also called a buckyball) is a
hollow cluster of 60 carbon atoms, all of which are sp2 hybridized, and which are joined together
in a pattern like the seams of a soccer ball. The center of the buckyball is large enough to
hold an atom of helium or argon, and such compounds are known. In the buckyball there are 32
interlocking rings: 20 are hexagons and 12 are pentagons, producing a highly symmetrical
molecule. A smaller symmetrical molecule, synthesized in 1982 by Leo A. Paquette and co-workers
at Ohio State University, is dodecahedrane.
One nal point: We began this book telling of how all of the carbon atoms of the universe are
thought to have been formed in the interiors of stars and to have been dispersed throughout the
universe when some of those stars exploded as supernovae. Consider this evidence. Sediments on
our planet, known to be 251 million years old and which were formed at the time of a great
extinction caused by the collision of a comet with Earth, have been found to contain buckyballs
with helium atoms in their centers. The isotopic ratio of 3He/4He in them is much larger than the
ratio in ordinary helium found on Earth now, indicating that the helium was of extraterrestrial
origin. So in these discoveries we have fascinating evidence for the origin of elemental carbon and
how some of it got here. Most carbon atoms were produced when Earth was formed billions of
years ago. But the carbon atoms of the buckyballs found in this sediment, formed originally in the
interior of a star somewhere in the universe, probably made their way here 251 million years ago
in a comet or meteorite.