text: While the formation of a sigma hole pair interaction is associated with energetic stabilization, this process is often thermodynamically disfavored as the energetic stabilization is often offset by a decrease in the entropy of the system. It has been shown that an enthalpy-entropy compensation relationship exists between the energetic and entropic changes associated with interactions, with more stabilizing interactions tending to result in larger entropy decreases. However, the decrease in entropy associated with the formation of a sigma hole interaction has been shown to approach a limiting value as the energetic favorability of the process is increased, and as such very energetically stabilizing interactions tend to be thermodynamically favored. There are additional factors that contribute to thermodynamic stability in the liquid and solid phases, which cannot be as easily modeled as gas phase interactions. As such, the favorability of a given sigma hole interaction in the liquid or solid phase may not necessarily match that of the gas phase equivalent.