Investigation on the aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms


Erdem S. H. , Ozpinar G. , Sacan M.

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, cilt.726, ss.233-243, 2005 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 726
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.theochem.2005.04.019
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
  • Sayfa Sayıları: ss.233-243

Özet

The aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms, and 1,3,4-thiadiazole, 1,3,4-oxadiazole, furan, thiophene, cyclopentadiene, the cyclopentadienyl anion and the cyclopentadienyl cation has been examined by harmonic oscillator measure of aromaticity (HOMA), aromatic stabilization energy (ASE), differential heat of hydrogenation (Delta Delta HH), and nucleus independent chemical shifts (NICS (0)), calculated at the HF/6-31G**, B3LYP/6-31G**, B3LYP/6-311G**, and B3LYP/6-311 + +G** levels. A principal component analysis (PCA) of the data set generated from these aromaticity results has been presented and compared with similar analyses in the recent literature. It has been shown that aromaticity is at least a two-dimensional phenomenon, independent of the level of the computational method employed. We observed that the sulfur-containing heterocyclic compounds are more aromatic than their oxygen analogs according to geometrical aromaticity measurements.