Thermodynamics of methanesulfonic acid, methanesulfonyl chloride, and methyl methanesulfonate

Article Abstract:

Heat of formation of liquid methanesulfonic acid, -178.09 +/-1.48, has been determined. The method was measuring the heat of the reaction in which methyl thiolacetate reacts with aqueous hypochlorite solution yielding aqueous methanesulfonate and acetate. Heats of formation of liquid methyl methanesulfonate and methanesulfonyl chloride have been found by measuring heats of reaction of methanesulfonyl chloride with methanol or water when a suitable basic catalyst is present. They are, respectively, -164.34 +/-1.58 and -126.91 +/-1.54. Heats of vaporization have been found based on vapor-pressure data, as have entropies, based on ab initio molecular orbital calculations. Free energies of transfer from gas phase to aqueous solution were calculated.

Measurement, Hydrolysis, Organochlorine compounds, Organic chlorine compounds, Thermal analysis, Vaporization, Heats of, Heat of vaporization

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A practical and efficient enantioselective synthesis of (2S)-3-(tert-butylsulfonyl)-2-benzylpropionic acid, a useful chiral building block for renin inhibitors

Article Abstract:

A compound, (2S)-3-(tert-butylsulfonyl)-2-benzylpropionic acid, which is at the N-terminal position of many renin inhibitors has because of that been of interest and it is synthesized by enantioselective hydrogenation using Ru-BINAP complexes with triethylamine with 84% ee from (Z)-2-(tert-butylsulfonylmethyl)-3-phenyl-2-propenoic acid. A substrate with sulfone functionality, 2-sulfonyl-substituted propenoic acid, has been enantioselectively hydrogenated as a means to developing a practical synthesis of the desired acid.

Canada, Chirality, Oxidation-reduction reaction, Oxidation-reduction reactions, Enantiomers, Hydrogenation, Renin

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