If carbon atoms 1, 2, 4 and 5 of cyclohexane occupy coplanar positions and when carbon atoms 3 and
6 are on opposite sides of the plane the
conformation (of symmetry group
D3d) is called a chair form. The same term is applied to similar conformations of
analogous saturated six-membered ring structures containing hetero-atoms and/or bearing substituent
groups, but these conformations may be distorted from the exact
D3d symmetry. For
cyclohexane and most such analogues, the chair form is the most
stable conformation. If the
cyclohexane
conformation has no centre of symmetry but possesses two planes of symmetry, one of
them bisecting the bonds between atoms 1 and 2 and between 4 and 5 and the other plane passing
through atoms 3 and 6 (which lie out of the plane and on the same side of the plane containing 1,
2, 4 and 5), that
conformation (of symmetry group
C2v ) is called a
boat form and it is
generally not a
stable form. Again, this term is also applied to structural analogues. The
conformation of
D2 symmetry passed through in the interconversion of two
boat forms of
cyclohexane is called the
twist form (also known as
skew boat,
skew form and stretched
form).
In a five-membered ring a
conformation in which two adjacent atoms are maximally displaced, in
opposite directions, relative to the plane containing the other three carbon atoms has been called a
half-chair but is better called a twist
conformation.
In carbohydrate chemistry the term twist refers to a five-membered ring
and the
D2 symmetry six-membered ring is referred to as
skew.
Source:
PAC, 1996, 68, 2193
(Basic terminology of stereochemistry (IUPAC Recommendations 1996))
on page 2202