Structure of Methanesulfonate Methylester

The sulfonate esters are easily subjected to nucleophilic substitution even under mild conditions. The sulfonate anion is a superb leaving group since the negative charge can be delocalized over several O-atoms. The para-toluenesulfonic esters are particularly useful and those are called the "tosylates". In that case further stabilization of the sulfonate leaving groups is achieved via delocalization into the benzene ring.


Figure. The MP2(full)/6-31G* optimized structure of methanesulfonate methylester.