Synthesis and characterization of o-fluorosulfinylaniline. A comparative vibrational study of fluorinated sulfinylanilines series

ANA LAURA PAEZ JEREZ; DIEGO JAVIER ALONSO DE ARMIÑO; NORMA LIS ROBLES

NEW JOURNAL OF CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2015

1144-0546

The synthesis of o-fluorosulfinylaniline is reported with the aim to complete the fluorinated sulfinylanilines series. The FT-IR and Raman spectra of o-fluorosulfinylaniline are recorded and the fundamental modes of its vibrational frequencies are assigned together with a tentative assignment of the NMR and mass spectra. Quantum chemical calculations on the optimized geometry predict in the liquid phase a planar structure with syn orientation of the N=S=O moiety (syn of the S=O double bond relative to the C‒N single bond), which belongs to CS symmetry group. The experimentally observed spectral data (FT-IR, Raman, 1H and 13C and GC-Mass Spectrometry) of the title compound are compared with those obtained theoretically from DFT calculations and gauge including atomic orbital (GIAO) method. Vibrational frequencies were assigned with the aid of anharmonic variational methods (VSCF) obtaining a significantly better agreement with experiment than with simple harmonic oscillator methods. Moreover, stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using Natural Bond Orbital (NBO) analysis.