Torsional strain cyclopentane

Cyclopropane (115 kj/mol strain) and cyclobutane (110.4 kj/mol strain) have both angle strain and torsional strain. Cyclopentane is free of angle strain but has a substantial torsional strain due to its large number of eclipsing interactions. Both cyclobutane and cyclopentane pucker slightly away from planarity to relieve torsional strain. 

Problem 4,10 How many H eclipsing interactions would be present if cyclopentane were planar Assuming an energy cost of 4.0 kj/mol for each eclipsing interaction, how much torsional strain would planar cyclopentane have Since the measured total Strain of cyclopentane is 26 kj/mol, how much of the torsional strain is relieved by puckering ... 

Cyclopentane, angle strain in. 116 conformation of, 116 molecular model of, 116 strain energy of, 114 torsional strain in, 116 Cyclopentanone. TR spectroscopy of, 731... 

In a similar way the potential constant method as described here allows the simultaneous vibrational analysis of systems which differ in other strain factors. Furthermore, conformations and enthalpies (and other properties see Section 6.5. for examples) may be calculated with the same force field. For instance, vibrational, conformational, and energetic properties of cyclopentane, cyclohexane and cyclodecane can be analysed simultaneously with a single common force field, despite the fact that these cycloalkanes involve different distributions of angle and torsional strain, and of nonbonded interactions 8, 17). This is not possible by means of conventional vibrational spectroscopic calculations. 

Cyclopentane has little torsional strain and angle strain. 

Cyclopentane assumes a slightly bent conformation => relieves some of the torsional strain. 

Thus cyclopentane molecule is flexible and shifts from one conformation to another constantly. With little torsional strain the molecule is as stable as cyclohexane. 

Conformational analysis of rings larger than cyclohexane is more complicated. These rings are also less common than cyclohexane, so we discuss their conformations only briefly. As can be seen from Table 6.1, the seven-membered ring compound cycloheptane has only a small amount of strain. Obviously, it is nonplanar to avoid angle strain. It does have some torsional strain, but the overall strain is comparable to that of cyclopentane. It is a fairly common ring system. 

Figure 9.6. Planar cyclopentane much torsional strain. Molecule actually puckered.

---