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Bicyclobutane is noted for being one of the most strained compounds that is isolatable on a large scale — its strain energy is estimated at 63.9 kcal mol −1. It is a nonplanar molecule, with a dihedral angle between the two cyclopropane rings of 123°.
The numbers are sometimes omitted in unambiguous cases. For example, bicyclo[1.1.0]butane is typically called simply bicyclobutane. The heterocyclic molecule DABCO has a total of 8 atoms in its bridged structure, hence the root name octane. Here the two bridgehead atoms are nitrogen instead of carbon atoms.
Cyclobutane-1,3-diyl is the planar four-membered carbon ring species with radical character localized at the 1 and 3 positions. The singlet cyclobutane-1,3-diyl is predicted to be the transition state for the ring inversion of bicyclobutane, proceeding via homolytic cleavage of the transannular carbon-carbon bond (Figure 3).
Norbornane (also called bicyclo[2.2.1]heptane). Unsubstituted cycloalkanes that contain a single ring in their molecular structure are typically named by adding the prefix "cyclo" to the name of the corresponding linear alkane with the same number of carbon atoms in its chain as the cycloalkane has in its ring.
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In alkanes, optimum overlap of atomic orbitals is achieved at 109.5°. The most common cyclic compounds have five or six carbons in their ring. [6] Adolf von Baeyer received a Nobel Prize in 1905 for the discovery of the Baeyer strain theory, which was an explanation of the relative stabilities of cyclic molecules in 1885.
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