The comparison of the electrochemical behaviour of N-tosylglycinoa nd N-dansylglycinew withthat of the corresponding amides and the benzenesulphonamidine in protic and aprotic media has shown thatthe RSO2- protected aminoacids, in their neutral form, can be considered as benzenesulphonamidederivatives and their E1/2 values fit the structural correlations among experimental and theoreticalparameters already discussed in previous papers. Using these correlations, the role of the RSO2- andcarboxylate groups on the amidic acidity of the free and complexed aminoacid has been determined also onthe basis of calculated differences in total energy of dissociated and undissociated acidic species. Allthese results confirm the main role played by the carboxylate group on the formation of N-O bidentatecomplexes.
Electrochemical behaviour of N-Tosylglycine and N-Dansylglycine in several solvents. The role of the RSO2- groups on the physico-chemical properties of Glycine / Fontanesi, Claudio; Borsari, Marco; Andreoli, A.; Benedetti, L.; Grandi, G.; Gavioli, G.. - In: ELECTROCHIMICA ACTA. - ISSN 0013-4686. - STAMPA. - 34:(1989), pp. 759-765.
Electrochemical behaviour of N-Tosylglycine and N-Dansylglycine in several solvents. The role of the RSO2- groups on the physico-chemical properties of Glycine
FONTANESI, Claudio;BORSARI, Marco;
1989
Abstract
The comparison of the electrochemical behaviour of N-tosylglycinoa nd N-dansylglycinew withthat of the corresponding amides and the benzenesulphonamidine in protic and aprotic media has shown thatthe RSO2- protected aminoacids, in their neutral form, can be considered as benzenesulphonamidederivatives and their E1/2 values fit the structural correlations among experimental and theoreticalparameters already discussed in previous papers. Using these correlations, the role of the RSO2- andcarboxylate groups on the amidic acidity of the free and complexed aminoacid has been determined also onthe basis of calculated differences in total energy of dissociated and undissociated acidic species. Allthese results confirm the main role played by the carboxylate group on the formation of N-O bidentatecomplexes.
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