"Allylic radicals, cations, and anions are unusually stable. In Lewis terms, this stabilization is readily explained by electron delocalization. In a molecular-orbital description, the three interacting p orbitals form three new molecular orbitals: One is considerably lower in energy than the p level, another one stays the same, and a third is higher in energy."
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K. Peter C. Vollhardt, Neil E. Schore (2011) Organic chemistry : structure and function 6th ed. Ch. 14 : Delocalized Pi Systems
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Allyl
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