Rogue Scholar

Publié 14 octobre 2012 in Henry Rzepa's Blog

There is often a disconnect between how a text-book (schematically) represents a reaction and a more quantitive “reality” revealed by quantum mechanics. Is the bromination of ethene to give 1,2-dibromoethane one such example? Text-books will show how ethene interacts with bromine to form a cyclic bromonium cation, which with the liberated bromide anion makes for an ion-pair.

References

Colloid and Surface ChemistryBiochemistryGeneral ChemistryCatalysis

Anglais

Stable Bromonium and Iodonium Ions of the Hindered Olefins Adamantylideneadamantane and Bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonane. X-Ray Structure, Transfer of Positive Halogens to Acceptor Olefins, and ab Initio Studies

https://doi.org/10.1021/ja00085a027

Publié 1 mars 1994 in Journal of the American Chemical Society

Auteurs R. S. Brown, R. W. Nagorski, A. J. Bennet, R. E. D. McClung, G. H. M. Aarts, M. Klobukowski, R. McDonald, B. D. Santarsiero

Colloid and Surface ChemistryBiochemistryGeneral ChemistryCatalysis

Anglais

The question of reversible formation of bromonium ions during the course of electrophilic bromination of olefins. 2. The crystal and molecular structure of the bromonium ion of adamantylideneadamantane

https://doi.org/10.1021/ja00301a021

Publié 1 juillet 1985 in Journal of the American Chemical Society

Auteurs H. Slebocka-Tilk, R. G. Ball, R. Stan Brown

Text-books and the bromination of ethene.

References

Stable Bromonium and Iodonium Ions of the Hindered Olefins Adamantylideneadamantane and Bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonane. X-Ray Structure, Transfer of Positive Halogens to Acceptor Olefins, and ab Initio Studies

The question of reversible formation of bromonium ions during the course of electrophilic bromination of olefins. 2. The crystal and molecular structure of the bromonium ion of adamantylideneadamantane