Theoretical Chemistry Accounts

, Volume 118, Issue 3, pp 597–606

Non-alkane behavior of cyclopropane and its derivatives: characterization of unconventional hydrogen bond interactions

  • Annia Galano
  • J. Raúl Alvarez-Idaboy
  • Annik Vivier-Bunge
Regular Article

Abstract

Eight cyclopropane derivatives (Δ − R) have been modeled, with R =  −H, −CH3, −NH2, −C ≡ CH, −C ≡ CCH3, −OH, −F and −C ≡ N. All geometries have been fully optimized at the MP2/ AUG-cc-pVTZ level of calculations. Natural bond orbital analyses reveal extra p character (spλ, λ > 3) in the C-C bonds of the cyclopropyl rings. The banana-like σCC bonds in the rings are described in detail. Alkene-like complexes between Δ − R molecules and hydrogen fluoride are identified. These weakly bonded complexes are formed through unconventional hydrogen bond interactions between the hydrogen atom in the HF molecule and the carbon–carbon bonds in the cyclopropane ring. A topological analysis of the electronic charge density and its Laplacian has been used to characterize the interactions. The possible relevance of such complexes in the modeling of substrate–receptor interactions in some anti-AIDS drugs is discussed.

Keywords

Cyclopropane Hybridization Natural bond orbitals Complex Bonding Alkene-like 

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Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • Annia Galano
    • 1
  • J. Raúl Alvarez-Idaboy
    • 2
  • Annik Vivier-Bunge
    • 3
  1. 1.Instituto Mexicano del PetróleoMéxico D. F.México
  2. 2.Facultad de QuímicaUniversidad Nacional Autónoma de MéxicoMéxico D.F.México
  3. 3.Área de Química Cuántica, Departamento de QuímicaUniversidad Autónoma MetropolitanaMéxico D.F.México

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