Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline

ANA LAURA PAEZ JEREZ; DOLY M. CHEMES; EDGARDO H. CUTIN; HEINZ OBERHAMMER,; NORMA L.ROBLES

NEW JOURNAL OF CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2015

1144-0546

The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra, are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the fluid phases syn structure of the ?N=S=O moiety (syn of the S=O double bond relative to the C‒N single bond). Both conformers belong to CS symmetry group and differ by relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman,1H and 13C and GC-Mass Spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, Natural Bond Orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.