Hydrogen Bonded Phenol-Quinolines with Highly Controlled Proton-Transfer Coordinate

Giovanny A. Parada, Starla D. Glover, Andreas Orthaber, Leif Hammarström, Sascha Ott

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A series of polycyclic phenols with intramolecular hydrogen bonds (IMHB) to quinolines was synthesized by Friedländer annulation of cycloalkanone-functionalized anisoles with 2-aminobenzaldehyde. The prepared compounds represent the first series of IMHB phenols in which the substitution and conjugation patterns between the phenols and the hydrogen bond acceptors are kept constant, and in which comparable electronic interaction between the two subunits is thus ensured. The distance and relative orientation between the phenolic OH and the quinolone nitrogen atom is controlled by 1,3-cycloalkadienes of different ring sizes to which the phenol and quinoline subunits are formally annulated.1H δ(OH) chemical shift and X-ray crystal structure characterization support the conclusion that the size and conformational preference of the 1,3-cycloalkadiene rings control the H-bond geometry and strength. As a result, the oxygen to nitrogen distances differ by as much as 0.30 Å across the series.

Original languageEnglish
Pages (from-to)3365-3372
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number20
DOIs
Publication statusPublished - 2016

Keywords

  • Conjugation
  • Donor–acceptor distance
  • Hydrogen bonds
  • Nitrogen heterocycles
  • Phenols

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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