Hybridization in Some Three-Membered Ring Organic Molecules

The molecular structures of some simple three-membered ring compounds, cyclopropane, cyclopropanone, ethylene oxide and ethylenimine, were studied by means of the orbital interaction between the fragments of a molecule. The relation between the carbon-carbon distance and the bending angle of the carbon-hydrogen bonds in ethylenic part of the three-membered rings is attributed primarily to the greater extent of mixing of the unoccupied π-like MO of ethylenic fragment into the occupied MO’s of rings. The increase in the bending angle as going from ethylene oxide to cyclopropane is interpreted in terms of the interaction of an occupied π-like orbital with the unoccupied α-like orbital of ethylenic fragment through the overlap with the orbital(s) of the residual part of rings. INDO MO and localized orbital calculations support the orbital interaction scheme. The same conclusion is derived also from the electrostatic theory of molecular geometries.

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