Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 7, pp 731–742 | Cite as

An experimental NMR and computational study of 4-quinolones and related compounds

  • Raquel S. G. R. Seixas
  • Artur M. S. Silva
  • Ibon Alkorta
  • José Elguero
Original Paper


We report the synthesis and structural study of eight compounds, either quinolin-4(1H)-ones or quinolines. Tautomerism as well as (E) → (Z) and rotational isomerism were studied both experimentally (1H and 13C NMR) and theoretically [B3LYP/6-311++G(d,p)].

Graphical Abstract


Thermal diastereomerization Quinolin-4(1H)-ones Tautomerism DFT calculations GIAO NMR spectroscopy 



Thanks are due to the University of Aveiro, FCT, and FEDER for funding the Organic Chemistry Research Unit, the Project POCI/QUI/58835/2004 and the Portuguese National NMR Network (RNRMN). R.S.G.R.S. also thanks FCT for her PhD Grant (SFRH/BD/30734/2006). We thank the Ministerio de Ciencia e Innovación (project no. CTQ2009-13129-C02-02), the Spanish MEC (CTQ2007-62113), and the Comunidad Autónoma de Madrid (project MADRISOLAR2, ref. S2009/PPQ-1533) for continuing support. Thanks are given to the CTI (CSIC) for an allocation of computer time.

Supplementary material

706_2011_473_MOESM1_ESM.doc (2.8 mb)
Supplementary material 1 (DOC 2,908 kb)


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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Raquel S. G. R. Seixas
    • 1
  • Artur M. S. Silva
    • 1
  • Ibon Alkorta
    • 2
  • José Elguero
    • 2
  1. 1.Chemistry Department and QOPNAUniversity of AveiroAveiroPortugal
  2. 2.Instituto de Química MédicaCSICMadridSpain

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