Phenylcarbamates, interaction with

The phenylcarbamates of polysaccharides also separate several nonpolar aromatic compounds,141 which cannot interact with the carbamate group through polar interaction. This indicates that, besides the polar interactions,... 

The derivatised glucose can act as a chiral site and result in diastereomeric interactions with enantiomers which together with the steric fit requirements within the cavity and the different interactions with the cellulose strands provides the basis for enantioselective interaction and subsequent resolution. The acetate, benzoate and phenylcarbamate glucose ester give superior resolution and selectivity compared with the parent material. Hydrophobic mobile phases are most commonly encountered though aqueous based eluants can be used with many versions of these materials. These stationary phase packings have been used to separate a wide range of pharmaceutical compounds [80]. 

There are five papers on carbamate chemistry of interest.6,84-87 The mechanism of the reaction in MeCN of /V-mcthyl-Af-phenylcarbamoyl chlorides (94) with benzyl-amines is believed to be XN2 based on Hammett p values, a cross-interaction constant pxy of —0.14, ku/ko values for the (V-deuteriated benzylamines all <1, and low activation enthalpies.84 The aminolysis of /Miitrophenyl A -phenylcarbamates in acetonitrile involving the I 1 (7) was discussed earlier.6 Solvolysis-decomposition of Af-l-adamantyl-/V-/ -tolylcarbamoyl chloride (95) in hydroxylic solvents involves a facile slow ionization (SN1 mechanism) giving a cation which eliminates ArNCO to... 

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