Equilibration of diamantan-1-ol and diamantan-4-ol. Conformational enthalpy of the hydroxy-group, and an unusual example of how entropy and symmetry factors can influence relative thermodynamic stabilities
Abstract
The isomeric diamantan-1- and -4-ols establish an equilibrium in 98% sulphuric acid at 273–473 K via a hydride transfer mechanism, and are equally thermo-dynamically stable at 321 K owing to differences in entropy values due to symmetry factors; the conformational enthalpy of the hydroxy-group is found to be 1·1 kcal mol–1.