Anti-entropic

As we affirmed in our discussion of thermodynamics, systems naturally tend toward a state of maximum entropy. Physical and chemical systems alike favor disorder. It is their natural state. Gases expand. Dyes distribute. Mixtures do whatever they can to dilute. Solutions do not want to lose solvent and become concentrated because there is more entropy in being dilute. The vapor pressure of a solution is lowered so the solution will not lose solvent and become more concentrated. The boiling point is elevated for the same reason. There is also more entropy for a liquid solution than for a solid, so solution freezing is anti-entropic. Hence, solutions experience... 

Etzioni, A. 1986. Rationality is anti-entropic. Journal of Economic Psychology, 1, pp. 17—36. 

Hydroamination involves the addition of primary or secondary amines to alkenes to afford terminal or branched higher value substituted amines via anti-Markovnikoff or Markovnikoff addition.144 Although the addition of RNH2 to C=C is thermodynamically favorable (Equation (14)), there is a strong entropic factor disfavoring N-H addition which has to be overcome through use of a metal catalyst. 

A benzene triplet state might be generated in the latter reaction which may account for the very negative entropy of activation in a cleavage reaction. This retro 2 + 2 reaction is entropically worse than that of the anti dimer which actually has a higher activation enthalpy. 

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