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It is not the case that The energetic conception of chemical bonding breaks down because bonding and molecule-wide stabilization can come apart.
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1.
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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2.
The most stable structure is stabilized by an unusually stable singlet state in which electron spins are parallel, not by conventional bonding.
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3.
The formation of a bond in this case actually produces a destabilized molecule rather than a stabilized one.
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