Theoretical study of the syn- and anti-conformers of 2,2ʹ-bifuran derivatives: rotational barrier and solvent effect

ABSTRACT

The optimised molecular structures, vibrational wavenumbers and corresponding vibrational assignments of the syn- and anti-conformers of 2,2ʹ-bifuran and its nitro, fluoro, methyl and hydroxyl derivatives were obtained using density functional theory. The starting structures with C₂ symmetry of all the ground state structures were considered and the transition state arising from syn-anti isomerisation was also modelled. All structures were fully optimised, and the geometries, dipole moments, charge, thermodynamic properties, and energies are reported. The calculated vibrational wavenumbers were assigned to the various fundamental modes of vibrations. The integral Equation Formalism Polarisation Continuum Model (IEF-PCM) was used to calculate the optimised geometry and the vibrational wavenumbers for all the compounds in different solvents. The results indicate that in the gas phase, the syn-conformer is more stable while in solution phases the conformational preference depends on the polarity of the solvent.

KEYWORDS:

• 2`-bifuran
• rotational barrier
• solvent effect
• density functional theory (DFT)

Disclosure statement

No potential conflict of interest was reported by the authors.

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