The electronic structure of 1,3-dipoles: hypervalent atoms
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1187-1197
- https://doi.org/10.1039/p29890001187
Abstract
Spin–coupled theory is applied to the π electrons of the 1,3-dipoles diazomethane, fulminic acid, and nitrone, and to the inorganic molecules O3, N2O, and NO2. The linear molecules are treated as planar species, in the spirit of 1,3-dipoles taking part in cycloaddition reactions as systems with four π electrons. A very simple, albeit unexpected picture arises for the bonding in these π-electron systems. The central nitrogen atom in CH2N2, for example, takes part in five covalent bonds. We use the label ‘hypervalent’ for such a situation, and we identify hypervalent atoms in all of the molecules considered. We discuss the consequences of our model for the chemistry and properties of 1,3-dipoles.Keywords
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