Theoretical considerations on the extended Boulton-Katritzky scheme

Károly Horváth, Dezsö Korbonits, G. Náray-Szabó, Kálmán Simon

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

It has been shown that in the rearrangement of 3-(2-aminoethyl)- and 3-(2-aminoaryl)-1,2,4-oxadiazoles the saturation of the side chain plays no decisive role from a mechanistic point of view, but the length of the side chain is the determining factor. The π-electronic system of the azole ring is also a prerequisite for a successful ring transformation. A linear correlation has been found between reactivity and CNDO/2 net charges on the N2 atom of the oxadiazole ring. The relative stabilities of the reacting species were assessed by CNDO/2 and ab initio geometry optimization calculations. The conformation of the side chains in two homologous molecules was analysed by X-ray diffraction.

Original languageEnglish
Pages (from-to)215-227
Number of pages13
JournalJournal of Molecular Structure: THEOCHEM
Volume136
Issue number3-4
DOIs
Publication statusPublished - 1986

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Oxadiazoles
Conformations
X ray diffraction
Azoles
Atoms
Molecules
Geometry
rings
X-Ray Diffraction
azoles
reactivity
saturation
optimization
geometry
electronics
diffraction
atoms
molecules
x rays

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Theoretical considerations on the extended Boulton-Katritzky scheme. / Horváth, Károly; Korbonits, Dezsö; Náray-Szabó, G.; Simon, Kálmán.

In: Journal of Molecular Structure: THEOCHEM, Vol. 136, No. 3-4, 1986, p. 215-227.

Research output: Contribution to journalArticle

Horváth, Károly ; Korbonits, Dezsö ; Náray-Szabó, G. ; Simon, Kálmán. / Theoretical considerations on the extended Boulton-Katritzky scheme. In: Journal of Molecular Structure: THEOCHEM. 1986 ; Vol. 136, No. 3-4. pp. 215-227.
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