Aromatic character of fluorinated pyridines


TOKATLI A. , AKYÜREKLİ S.

STRUCTURAL CHEMISTRY, cilt.24, ss.445-454, 2013 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 24 Konu: 2
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1007/s11224-012-0097-9
  • Dergi Adı: STRUCTURAL CHEMISTRY
  • Sayfa Sayıları: ss.445-454

Özet

Geometric structures for all the possible isomers of fluorinated pyridines were optimized at the B3LYP/6-311++G(d,p) level of theory. Aromaticities of the considered molecules were investigated using different indices included geometry-based (HOMA and Bird [I (6)]), magnetism-based (NICS(1) and diamagnetic susceptibility anisotropy [Delta chi]), pi- and sigma-electron count-based (pEDA, sEDA), and recently introduced electronic-based (electric field gradient [EFG(0), EFG(0.5)] and Shannon aromaticity) indices. Moreover, we used also HOMO-LUMO gap, atomization energy (D (0)), and interaction energy for fluorinated pyridine complexes by water molecule as global descriptors, and the EFG values (EFG(C-F)(0)) on the middle points of C-F bonds and sigma-electron population (N (sigma)) of nitrogen atom as local descriptors. All studied indices except HOMA and EFG(0.5) are well correlated to each other and to global and local descriptors.