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    Among the four structural isomers of 2-methylenecyclopent... — Carmelics
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    Challenges→The energetic conception of chemical bonding breaks down because bonding and molecule-wide stabilization can come apart.

    Among the four structural isomers of 2-methylenecyclopentane-1,3-diyl, the most stable structure does not correspond to a normal bonding interaction.

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    Another line of objection comes from Berson (2008), who discusses the significance of very weakly bonded molecules. For example, there are four structural isomers of 2-methylenecyclopentane-1,3-diyl. The most stable of the structures does not correspond to a normal bonding interaction because of an unusually stable singlet state, a state where the electron spins are parallel. Berson suggests that this is a case where “the formation of a bond actually produces a destabilized molecule.” In other w

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