The effect of β-cyclodextrin (β-CD) on the mononuclear heterocyclic rearrangement of the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1) in aqueous borate buffer at pH = 9.6 has been analyzed at temperatures ranging from 293.15 to 313.15 K. The trend of the absorption spectra of 1 as a function of time has been accounted for with the formation of two different 1:1 complexes between β-CD and 1, the first, "unreactive" complex being formed faster than the "reactive" one. The occurrence of negative activation enthalpy values for the studied interconversion evidences the kinetic relevance of inclusion processes. Computational models elaborated using the MM2 molecular mechanics force field give an idea of the relative importance of the different complexes, additionally helping us to formulate a suitable reaction scheme.

Guernelli S., Lagana M.F., Spinelli D., Lo Meo P.L., Noto R., Riela S. (2002). Host-guest interactions between β-cyclodextrin and the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole: The first kinetic study of a ring-ring interconversion in a "confined environment". JOURNAL OF ORGANIC CHEMISTRY, 67(9), 2948-2953 [10.1021/jo016214w].

Host-guest interactions between β-cyclodextrin and the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole: The first kinetic study of a ring-ring interconversion in a "confined environment"

Guernelli S.;Lagana M. F.;
2002

Abstract

The effect of β-cyclodextrin (β-CD) on the mononuclear heterocyclic rearrangement of the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1) in aqueous borate buffer at pH = 9.6 has been analyzed at temperatures ranging from 293.15 to 313.15 K. The trend of the absorption spectra of 1 as a function of time has been accounted for with the formation of two different 1:1 complexes between β-CD and 1, the first, "unreactive" complex being formed faster than the "reactive" one. The occurrence of negative activation enthalpy values for the studied interconversion evidences the kinetic relevance of inclusion processes. Computational models elaborated using the MM2 molecular mechanics force field give an idea of the relative importance of the different complexes, additionally helping us to formulate a suitable reaction scheme.
2002
Guernelli S., Lagana M.F., Spinelli D., Lo Meo P.L., Noto R., Riela S. (2002). Host-guest interactions between β-cyclodextrin and the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole: The first kinetic study of a ring-ring interconversion in a "confined environment". JOURNAL OF ORGANIC CHEMISTRY, 67(9), 2948-2953 [10.1021/jo016214w].
Guernelli S.; Lagana M.F.; Spinelli D.; Lo Meo P.L.; Noto R.; Riela S.
File in questo prodotto:
Eventuali allegati, non sono esposti

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/11585/777836
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 24
social impact