Conformational and NMR study of some furan derivatives by DFT methods

David Santos-Carballal, Reynier Suardíaz*, Rachel Crespo-Otero, Leandro González, Carlos S. Pérez

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

Abstract

4′-substituted neutral/protonated furfurylidenanilines and trans-styrylfurans are able to exist in two different conformations related to the rotation around the furan ring-bridge double bond. In this work, the equilibrium geometry and the corresponding rotational barrier of the benzene ring for each furan derivative conformation were calculated by DFT methods. The trend and shape of the rotational barrier are rationalized within natural bond orbitals as well as atoms-in-molecules approach. For the corresponding equilibrium geometries, 1H and 13C substituent induced shifts (SIS) were calculated and compared with experimental values. Calculated shielding constants are shown to be sensitive to the substituent effect through a linear fit with substituent's Hammett constants. An alternative approach was followed for assessing the effect of substituents over SIS through comparing the differences in isotropic shielding constants with NBO charges as well as with 1H and 13C experimental chemical shifts.

Original languageEnglish
Pages (from-to)4591-4601
Number of pages11
JournalJournal of Molecular Modeling
Volume19
Issue number10
DOIs
Publication statusPublished - Oct 2013

Keywords

  • Chemical shifts
  • Furfurylidenanilines
  • Rotational barriers
  • Styrylfurans

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