Journal of Molecular Modeling

, Volume 17, Issue 12, pp 3209–3217 | Cite as

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

  • Gül Altınbaş Özpınar
  • Dieter E. Kaufmann
  • Timothy Clark
Original Paper
First Online:
Received:
Accepted:

Abstract

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 − 31 + G**, 6 − 311++G**, 6 − 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.

Keywords

Ab initio DFT Vilsmeier reaction 
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Notes

Acknowledgments

We thank the Excellence Cluster Engineering of Advanced Materials (funded by the Deutsche Forschungsgemeinschaft) for financial support.

Supplementary material

894_2010_941_MOESM1_ESM.pdf (461 kb)
Supplementary information (PDF 460 kb)

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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Gül Altınbaş Özpınar
    • 1
    • 2
    • 3
  • Dieter E. Kaufmann
    • 4
  • Timothy Clark
    • 1
    • 2
  1. 1.Computer-Chemie-CentrumFriedrich-Alexander-Universität Erlangen-NürnbergErlangenGermany
  2. 2.Excellence Cluster Engineering of Advanced MaterialsFriedrich-Alexander-Universität Erlangen-NürnbergErlangenGermany
  3. 3.Department of Chemistry, Faculty of Science and LettersKırklareli UniversityKırklareliTurkey
  4. 4.Technische Universität ClausthalInstitut für Organische ChemieClausthal-ZellerfeldGermany

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