Conformational Analysis of 2-Substituted Cyclobutane-alfa-Amino Acid Derivatives. A Synergistic Experimental and Computational Study

  1. Jiménez-Osés, G. 1
  2. Corzana, F. 1
  3. Busto, J.H. 1
  4. Pérez-Fernández, M. 1
  5. Peregrina, J.M. 1
  6. Avenoza, A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2006

Volumen: 71

Número: 5

Páginas: 1869-1878

Tipo: Artículo

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DOI: 10.1021/JO0521955 SCOPUS: 2-s2.0-33644650028 WoS: WOS:000235896800014 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

Resumen

An extensive conformational study of different 2-substituted cyclobutane-α-amino acid derivatives in the solid state, in the gas phase, and in solution has been carried out. The study combines experimental techniques, such as X-ray diffraction and NMR spectroscopy, and computational methods, such as DFT calculations and molecular dynamics (MD) simulations, in a set solvent. The study reveals that the substituent at C2 in the cyclobutane ring, when fixed in an equatorial position, modulates the conformational preference of the ring-puckering. © 2006 American Chemical Society.