Strained Small Nitrogen Heterocycles‐Azabicyclobutanes and Azirines

Abstract: Small ring nitrogen heterocycles, azabicyclobutanes and azirines, were investigated by computational methods in order to address the discrepancy between their regioisomers 1‐ and 2‐azabicyclobutane and 1H‐ and 2H‐azirines. Both 1‐azabicyclobutane and 2H‐azirine are well known synthetic starting points to larger nitrogen heterocycles whereas 2‐azabicyclobutane and 1H‐azirine and their derivatives have yet to be reported as isolable compounds. Calculated parameters such as structure, base strength (proton affinities), NICS values and enthalpies of formation from which strain energies are derived are reported. The destabilization of the less stable regioisomers is attributed to homoantiaromaticity in 2‐azabicyclobutane and antiaromaticity in 1H‐azirine. Two stereoisomers exist for 2‐azabicyclobutane with the endo‐ stereoisomer being more stable. This phenomenon is indicative of the hydrogen bond acceptor properties of the neighboring cyclpropane and the π‐bond character of the central bond in 2‐azabicyclobutane.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Strained Small Nitrogen Heterocycles‐Azabicyclobutanes and Azirines ; volume:8 ; number:26 ; year:2023 ; extent:13
ChemistrySelect ; 8, Heft 26 (2023) (gesamt 13)

Urheber
Rágyanszki, Anita
Fiser, Béla
Lee‐Ruff, Edward
Liebman, Joel F.

DOI
10.1002/slct.202301405
URN
urn:nbn:de:101:1-2023071115365566100272
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
14.08.2025, 10:55 MESZ

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Beteiligte

  • Rágyanszki, Anita
  • Fiser, Béla
  • Lee‐Ruff, Edward
  • Liebman, Joel F.

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