The conformational preferences of beta-sulfonamidopeptides in chloroform solution were investigated by variable-temperature H-1 NMR spectroscopy and FT-IR spectroscopy. The following hydrogen-bonding acceptor scale was derived from the experiments: RCON approximate to tBuOCON > COOMe greater than or equal to RSO2N. An intermolecular study gave results complementary to those described above: the N-H stretch bands of N-methylacetamide and N-methyl methanesulfonamide in chloroform were followed during titration with excess methanesulfonylpyrrolidine and N,N-dimethylacetamide. Shifts to lower frequencies were observed which are correlated with the hydrogen-bond strengths and show that the amide is a stronger hydrogen-bond acceptor than the sulfonamide.

Hydrogen-bonding donor/acceptor scales in beta-sulfonamidopeptides / C.M.A. Gennari, M. Gude, D. Potenza, U. Piarulli. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 4:10(1998), pp. 1924-1931.

Hydrogen-bonding donor/acceptor scales in beta-sulfonamidopeptides

C.M.A. Gennari
Primo
;
D. Potenza
Penultimo
;
1998

Abstract

The conformational preferences of beta-sulfonamidopeptides in chloroform solution were investigated by variable-temperature H-1 NMR spectroscopy and FT-IR spectroscopy. The following hydrogen-bonding acceptor scale was derived from the experiments: RCON approximate to tBuOCON > COOMe greater than or equal to RSO2N. An intermolecular study gave results complementary to those described above: the N-H stretch bands of N-methylacetamide and N-methyl methanesulfonamide in chloroform were followed during titration with excess methanesulfonylpyrrolidine and N,N-dimethylacetamide. Shifts to lower frequencies were observed which are correlated with the hydrogen-bond strengths and show that the amide is a stronger hydrogen-bond acceptor than the sulfonamide.
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175573
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 68
  • ???jsp.display-item.citation.isi??? 65
social impact