N-(2,4,6-Trimethylphenyl)formamide C10H13NO
2011
Unexpected Formation of N-Mesityl-Formamide
publication
Evidence: moderate
Author Information
Author(s): Marilé Landman, Belinda avan der Westhuizen, Daniela I. Bezuidenhout, David C. Liles
Primary Institution: University of Pretoria
Hypothesis
The study investigates the unexpected formation of N-(2,4,6-trimethylphenyl)formamide during the synthesis of a manganese(I)–N-heterocyclic carbene complex.
Conclusion
N-mesityl-formamide was formed almost exclusively instead of the target manganese complex.
Supporting Evidence
- The dihedral angle between the planes of the formamide moiety and the aryl ring is 68.06°.
- Molecules are linked by N—H⋯O hydrogen bonds, forming infinite chains along the c axis.
- The unexpected product was formed due to side reactions during the synthesis process.
Takeaway
The researchers tried to make a specific chemical compound but ended up making a different one instead, which was surprising.
Methodology
The synthesis involved stirring Mn(CO)5Br and Me3NO in THF, followed by deprotonation of IMesHCl and separation of products using chromatography.
Digital Object Identifier (DOI)
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