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

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

Journal of molecular modeling (2011-03-03)
Gül Altınbaş Ozpınar, Dieter E Kaufmann, Timothy Clark
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Phosphorus(V) oxychloride, 99.999%
Sigma-Aldrich
Phosphorus(V) oxychloride, ReagentPlus®, 99%