Room Temperature Ionic Liquids Structure and its Effect on the Mononuclear Rearrangement of Heterocycles:  An Approach Using Thermodynamic Parameters

Francesca D'Anna,*† Vincenzo Frenna,† Renato Noto,*† Vitalba Pace,† and Domenico Spinelli*‡; ;
Dipartimento di Chimica Organica E. Patern, Universit degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans 2, 90128 Palermo, Italy, and Dipartimento di Chimica Organica A. Mangini, Universit degli Studi di Bologna, Via San Giacomo 11, 40126 Bologna, Italy
J. Org. Chem., 2006, 71 (26), pp 9637–9642
DOI: 10.1021/jo0615549
Publication Date (Web): November 21, 2006
Copyright © 2006 American Chemical Society
*

 To whom correspondence should be addressed. Phone:  +39091596919 (F.D., R.N.); +390512095689 (D.S.). Fax:  +39091596825 (F.D., R.N.); +390512095688 (D.S.).

,
†

 Dipartimento di Chimica Organica “E. Paternò”.

,
‡

 Dipartimento di Chimica Organica “A. Mangini”.

, fdanna@unipa.it, ; , rnoto@unipa.it, ; , domenico.spinelli@unibo.it

Abstract

Abstract Image

The kinetics of the rearrangement of the Z-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1) into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole (2) induced by amines have been studied in five room-temperature ionic liquids (RTILs) at different temperatures. The kinetic data collected show that both cationic and anionic parts of RTILs significantly influence the reactivity of the title reaction. The calculated activation parameters allow us to advance hypotheses about the weak interactions operating in RTIL solutions.

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History

  • Published In Issue December 22, 2006
  • Received July 27, 2006

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