Abstract
o-Thioquinones can undergo either [2 + 4] or [4 + 2] cycloaddition reactions with acyclic dienes. To illustrate the bonding processes in these cycloadditions, the natural orbital Fukui function (NOFF) and bonding reactivity descriptor have been employed. The electrophilicity of a bond or an orbital in the o-thioquinone as well as in the acyclic diene has been found using the NOFF, which suggests that electron transfer takes place from an electron-donating bonding orbital to an electron-accepting antibonding/bonding orbital, leading to the cyclic product via the formation of a circular loop and two covalent bonds. The bonding reactivity descriptor shows that covalent bonds readily form between atom k1 of one molecule with a large f(k1)(+) value and atom k2 of another molecule with a large f(k2)(-) value. Both the NOFF and the bonding reactivity descriptor are efficient tools for interpreting the mechanism underlying the [2 + 4] and [4 + 2] cycloaddition between o-thioquinones and acyclic dienes.
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