Formation of the Vilsmeier-Haack complex: the performance of different levels of theory

Ozpinar G. , Kaufmann D. E. , Clark T.

JOURNAL OF MOLECULAR MODELING, cilt.17, ss.3209-3217, 2011 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 17 Konu: 12
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1007/s00894-010-0941-z
  • Dergi Adı: JOURNAL OF MOLECULAR MODELING
  • Sayfa Sayıları: ss.3209-3217

Özet

Because of discrepancies in the available experimental data, an extensive theoretical investigation of the formation of the Vilsmeier-Haack (VH) complex has been carried out. The barriers to complex formation calculated using eight different density functional methods (BLYP, B2-PLYP, B3LYP, B3PW91, MPW1K, M06-2X, and PBE1PBE), MP2, and extrapolation techniques (CBS-QB3, G3B3) with several basis sets (6 -aEuro parts per thousand 31 + G**, 6 -aEuro parts per thousand 311++G**, 6 -aEuro parts per thousand 311 + (3df,2p), aug-cc-pVDZ, and aug-cc-pVTZ) were compared with experimental data. For the overall reaction, MP2/aug-cc-pVDZ and M06-2X/6-31 + G(d,p) perform best compared to the CBS techniques. The results help clarify some open mechanistic questions.