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Concept
Eclipsed conformation
Summary
In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. Such a conformation can exist in any open chain, single chemical bond connecting two sp3-hybridised atoms, and it is normally a conformational energy maximum. This maximum is often explained by steric hindrance, but its origins sometimes actually lie in hyperconjugation (as when the eclipsing interaction is of two hydrogen atoms).
In order to gain a deeper understanding of eclipsed conformations in organic chemistry, it is first important to understand how organic molecules are arranged around bonds, as well as how they move and rotate.
In the example of ethane, two methyl groups are connected with a carbon-carbon sigma bond, just as one might connect two Lego pieces through a single “stud” and “tube”. With this image in mind, if the methyl groups are rotated around the bond, they will remain connected; however, the shape will change. This leads to multiple possible three-dimensional arrangements, known as conformations, conformational isomers (conformers), or sometimes rotational isomers (rotamers).
Conformations can be described by dihedral angles, which are used to determine the placements of atoms and their distance from one another and can be visualized by Newman projections. A dihedral angle can indicate staggered and eclipsed orientation, but is specifically used to determine the angle between two specific atoms on opposing carbons. Different conformations have unequal energies, creating an energy barrier to bond rotation which is known as torsional strain. In particular, eclipsed conformations tend to have raised energies due to the repulsion of the electron clouds of the eclipsed substituents. The relative energies of different conformations can be visualized using graphs. In the example of ethane, such a graph shows that rotation around the carbon-carbon bond is not entirely free but that an energy barrier exists.
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