The
second half of the double bond in ethylene arises from a combination
of these last two p orbitals into a molecular
orbital with z lobes of density of opposite sign above and below
the plane of the molecule. The double bond is shorter than a single
bond because the p. orbitals must come closer together before they
overlap enough to bond. The orbital
also forces the molecule to be planar. Twisting about a bond axis
is harmless to a symmetrical s, bond,
but breaks a p bond by pulling the p
orbitals out of alignment. To twist one end of the ethylene molecule
90 relative
to the other, one would have to supply energy equal to the difference
between a C-C double bond and a single bond, or 147 - 83 = 64 kcal
mole.
The ideal H-C-H bond angle of 120
at each end of the ethylene molecule is decreased to 117
by electron-pair repulsion between the double bond and the two C-H
single bonds. Double bonds are of great importance in biological
molecules, both because they help make proteins and other molecules
rigid and because of their unique ability to absorb light. We will
come back to the structural rigidity aspects in the chapter on proteins,
and to their light-absorbing properties in the postscript to this
chapter.