The "hydrazinoturn" hydrogen bonding network in hydrazinopeptides and aza-β3-peptides as probed by an AIM topological analysis of the electronic density

Cyrille Simo, Arnaud Salaün, Clément Arnarez, Lucie Delemotte, Alexandre Haegy, Ali Kachmar, Adèle D. Laurent, Jennifer Thomas, Brigitte Jamart-Grégoire, Philippe Le Grel, Alexandre Hocquet

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Abstract

This paper follows a previous publication [Salaün, A., et al., Conformation of Nα-substituted hydrazino acetamides in CDCl3, the precious help of the analysis of Δδ between amidic hydrogens, and correlation to the conformation of Aza-β3-peptides. J. Org. Chem. 71 (2006) 150-158] where the so called "hydrazinoturn" hydrogen bond network is assessed in aza-β3-peptides, as modeled by selected representative hydrazinoacetamides, on the basis of proton NMR. In this paper, DFT theoretical calculations at the B3LYP/6-311G++(d,p) level of theory are described in order to shed light on the intramolecular hydrogen bond network of the same molecules. The analysis is carried on by means of the AIM topological analysis of the electronic density.

Original languageEnglish
Pages (from-to)41-46
Number of pages6
JournalJournal of Molecular Structure: THEOCHEM
Volume869
Issue number1-3
DOIs
Publication statusPublished - 30 Nov 2008

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Keywords

  • AIM
  • Aza-β-peptides
  • Bifurcated hydrogen bonding
  • Hydrazinopeptides
  • Hydrazinoturn

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Cite this

Simo, C., Salaün, A., Arnarez, C., Delemotte, L., Haegy, A., Kachmar, A., Laurent, A. D., Thomas, J., Jamart-Grégoire, B., Le Grel, P., & Hocquet, A. (2008). The "hydrazinoturn" hydrogen bonding network in hydrazinopeptides and aza-β3-peptides as probed by an AIM topological analysis of the electronic density. Journal of Molecular Structure: THEOCHEM, 869(1-3), 41-46. https://doi.org/10.1016/j.theochem.2008.08.019