Behind the reactivity of lactones: A computational and spectroscopic study of phenol·γ-butyrolactone

  1. León, I. 1
  2. González, Jorge. 1
  3. Millán, J. 2
  4. Castaño, F. 1
  5. Fernández, J.A. 1
  1. 1 Universidad del País Vasco/Euskal Herriko Unibertsitatea
    info

    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment & General Theory

ISSN: 1089-5639

Año de publicación: 2014

Volumen: 118

Número: 14

Páginas: 2568-2575

Tipo: Artículo

DOI: 10.1021/JP4103417 SCOPUS: 2-s2.0-84898489868 WoS: WOS:000334573000002 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment & General Theory

Resumen

In this work, the intermolecular interaction between phenol and γ-butyrolactone (GBL) has been studied by a combination of spectroscopic and computational techniques the electronic and vibrational transitions of phenol·GBL were measured in a supersonic jet expansion by resonant two-photon ionization (R2PI) and ion dip IR (IDIR) spectroscopy the results obtained were compared with calculations carried out with both M06-2X and MP2 molecular orbital methods in order to characterize the intermolecular interactions the singly detected conformer is stabilized by a relatively strong hydrogen bond in which phenol acts as a proton donor to the carbonyl group of GBL the phenol·GBL2 cluster has also been studied, finding up to three populated conformers. Nevertheless, in the three species, the main interaction between the phenolic hydroxyl group and the GBL?s carbonyl group remains similar to that of phenol·GBL. Furthermore, the C=O···H interaction is reinforced. © 2014 American Chemical Society.