Summary
In chemistry, a molecule experiences strain when its chemical structure undergoes some stress which raises its internal energy in comparison to a strain-free reference compound. The internal energy of a molecule consists of all the energy stored within it. A strained molecule has an additional amount of internal energy which an unstrained molecule does not. This extra internal energy, or strain energy, can be likened to a compressed spring. Much like a compressed spring must be held in place to prevent release of its potential energy, a molecule can be held in an energetically unfavorable conformation by the bonds within that molecule. Without the bonds holding the conformation in place, the strain energy would be released. The equilibrium of two molecular conformations is determined by the difference in Gibbs free energy of the two conformations. From this energy difference, the equilibrium constant for the two conformations can be determined. If there is a decrease in Gibbs free energy from one state to another, this transformation is spontaneous and the lower energy state is more stable. A highly strained, higher energy molecular conformation will spontaneously convert to the lower energy molecular conformation. Enthalpy and entropy are related to Gibbs free energy through the equation (at a constant temperature): Enthalpy is typically the more important thermodynamic function for determining a more stable molecular conformation. While there are different types of strain, the strain energy associated with all of them is due to the weakening of bonds within the molecule. Since enthalpy is usually more important, entropy can often be ignored. This isn't always the case; if the difference in enthalpy is small, entropy can have a larger effect on the equilibrium. For example, n-butane has two possible conformations, anti and gauche. The anti conformation is more stable by 0.9 kcal mol−1. We would expect that butane is roughly 82% anti and 18% gauche at room temperature. However, there are two possible gauche conformations and only one anti conformation.
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