# Cyclopentane conformations

What is the energy minimum of cyclopentane conformational diagram: the halfchair or envelope? How does cyclopentane flip?

In the absence of substituents around the ring, there is actually only a $$\pu{0.5 kcal/mol}$$ energy difference between envelope and half-chair (envelope slightly lower in energy) meaning cyclopentane itself (computationally at least) is in rapid equilibration with no 'major' conformation as is observed with cyclohexane. (Note that the energy of the totally planar conformation is about $$\pu{5 kcal/mol}$$ higher than that of the both bent conformations, and so is not observed to any great degree).
With a single substituent on the ring however, such as a methyl group, the envelope conformation becomes slightly more favourable (to the tune of around $$\pu{3.5 kcal/mol}$$) giving a barrier to the ring flipping and meaning there is a dominant conformation.
• Why do you show two C$_s$ envelope conformations? Is not the left one the same as the right after a rotation. As all the 5 possible envelope-half-chairs are equally probable surely only one envelope and half chair is needed ? As thermal energy is approx 2.4 kJ/mol interconversion should be very rapid, I'm guessing but $10^8$ s$^{-1}$ would not be unreasonable. – porphyrin Jul 24 '16 at 12:55