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The iconic diagram below represents a cornerstone of organic chemistry. Generations of chemists have learnt early on in their studies of the subject that these two representations of where the electron pairs in benzene might be located (formally called electronic...

This story starts with an organic chemistry tutorial, when a student asked for clarification of the Finkelstein reaction. This a simple SN2 type displacement of an alkyl chloride or bromide, using sodium iodide in acetone solution, and resulting in an alkyl...

In the previous post, it was noted that Mbius annulenes are intrinsically chiral, and should therefore in principle be capable of resolution into enantiomers. The synthesis of such an annulene by Herges and co-workers was a racemic one; no attempt was reported...

In 1988, Wilke (DOI: 10.1002/anie.198801851) reported molecule 1A 24-annulene. Click on image for model.It was a highly unexpected outcome of a nickel-catalyzed reaction and was described as a 24-annulene with an unusual 3D shape. Little attention has been...

The diagram below summarizes an interesting result recently reported by Hanson and co-workers (DOI: 10.1021/jo800706y. At ~neutral pH, compound 13 hydrolyses with a half life of 21 minutes, whereas 14 takes 840 minutes. Understanding this difference in reactivity...

Mauksch and Tsogoeva have recently published an article illustrating how a thermal electrocyclic reaction can proceed with distoratory ring closure, whilst simultaneously also exhibiting 4n electron Mbius-aromatic character (DOI 10.1002/anie.200806009). Why...

Henry Rzepa made an interesting post on rationalizing the difference in half lives of amide hydrolysis in closely related molecules using molecular mechanics. Why not try it for yourself using Avogadro?The screencast shows you how to build the molecules (using...

Careful consideration of orbital topolologies of pericyclic reactions has led to the recent flurry of activity related to Möbius aromaticity, homoaromaticity, and antiaromaticity. I discussed this briefly in Chapter 2 of the book and in these posts (1,...

Careful consideration of orbital topolologies of pericyclic reactions has led to the recent flurry of activity related to Möbius aromaticity, homoaromaticity, and antiaromaticity. I discussed this briefly in Chapter 2 of the book and in these posts (1,...