On the behaviour of the (Z)-Phenylhydrazones of some5-alkyl-3-benzoyl-1,2,4-oxadiazoles in solution and in the gasphase: kinetic and spectrometric evidence in favour of self-assembly

Paolo Maria Giuseppe Lo Meo, Renato Noto, Egon Rizzato, Antonella Fontana, Elisabetta Mezzina, Susanna Guernelli, Stefano Morganti, Domenico Spinelli, Romina Zappacosta

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Abstract

Rate constants, kA,R, for the rearrangement of the (Z )-phenylhydrazones (1aee) of a series of 5-alkyl-3-benzoyl-1,2,4-oxadiazoles substituted at C(5) with linear alkyl chains of different length (from C4 up to C12) into the relevant 4-acylamino-2,5-diphenyl-1,2,3-triazoles (2aee) have been measured in dioxan/water in the base-catalyzed region (pSþ 10.5e12.6). For each substrate log kA,R are linearly related to pSþ. The significant decrease of the slopes of these straight lines (from 0.96 down to 0.78) upon increasing the length of the linear alkyl chain at C(5) and that of the reactivity (down to 14e26%) upon increasing the substrate concentration suggest a decrease of the polarity of the ‘actual’ reaction medium and provide indirect evidence of the tendency of the substrates (Z )-1aee to self-assemble. To confirm the above outcome direct evidence of the formation of self-assemblies in solution were obtained from 1H NMR and spectrofluorimetry measurements while ESI-MS experiments point out the presence of aggregated substrates also in the gas phase.
Original languageEnglish
Pages (from-to)733-740
Number of pages8
JournalTetrahedron
Volume64
Publication statusPublished - 2008

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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