Illustrated Glossary of Organic Chemistry
Torsional
strain
(Pitzer
strain
):
Strain
caused by the close approach of atoms or
groups
separated by three
covalent bonds
. In the
molecule
W-X-Y-Z, atoms W and Z may experience torsional
strain
if a particular
conformation
(such as an
eclipsed conformation
) brings these atoms into close proximity. Torsional
strain
can cause a resistance to
bond rotation
, and can influence a
barrier to rotation
. (Student confusion over the definitions of torsional
strain
versus other types of
strain
was the impetus to start the Illustrated Glossary of
Organic Chemistry
.)
Sawhorse projections
:
Newman projections
:
Eclipsed conformation
More
strain
Anti-staggered conformation
Less
strain
When the chlorine atoms of 1,2-dichloro
ethane
are aligned (an
eclipsed conformation
), the chlorine atoms experience torsional
strain
. The
eclipsed
hydrogen atoms also experience torsional
strain
(albeit less than the chlorine atoms because hydrogen has a smaller
atomic radius
than chlorine). This torsional
strain
is relieved when carbon-carbon
bond rotation
changes the
molecule
into a
staggered conformation
(such as the
anti-staggered conformation
shown here).
Verify this with
molecular models
.
Related terms:
Angle strain
,
ring strain
,
steric strain
Wikipedia entry
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