Fornarini, Simonetta published an article on February 3 ,1988. The article was titled 《Positive evidence for tetrahedral R’C(OR)3H+ intermediates in the gas phase》, and you may find the article in Journal of the American Chemical Society.Computed Properties of C9H5F5O2 The information in the text is summarized as follows:
Cationic alcoholysis of esters was studied in the gas phase at nearly atm. pressures to establish a bridge between the predominant addition-elimination mechanism typical of carboxylic acid derivatives in solution and the concerted alkyl- (or acyl-)group transfer prevailing in ICR studies at low pressure. Operation of the 1st mechanism, involving tetrahedral intermediates, was inferred using CD3OD and Me18OH in radiolytic and chem.-ionization experiments and, most conclusively, by the actual isolation of neutral ortho esters, obtained by trapping the intermediate with a highly basic, poorly nucleophilic amine. Thus, gas-phase experiments lend themselves to meaningful correlation with solution-chem. data only at sufficiently high pressure. The experimental process involved the reaction of Ethyl 2,3,4,5,6-pentafluorobenzoate(cas: 4522-93-4Computed Properties of C9H5F5O2)
Ethyl 2,3,4,5,6-pentafluorobenzoate(cas: 4522-93-4) belongs to esters. They are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market.Computed Properties of C9H5F5O2
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics