Electronic Structures of Naphthalenediols. II. β, β′-Naphthalenediols

概要

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The molecular diagrams and extradelocalization energies of the 2,3-, 2,6- and 2,7-naphthalenediols were calculated by using the LCAO MO method. To elucidate the effect of the 9–10 bond on the molecular properties of naphthalene derivatives, we carried out calculations of the electronic structures of naphthalene hydroxy derivatives based on the perimeter model. These calculations proved that: 1) The 3-position in the naphthalene derivatives in less reative than the other positions. 2) The α-derivatives are more stable than the β-derivatives. 3) The insertion of the 9–10 bond in the perimeter model causes a decrease in the degree of conjugation interactions among the ring and the substituents. 4) In the cases of A, A-derivatives, the substituents have no significant influence on the unsubstituted ring, but produce rather a large effect on the substituted rings. 5) α-Substitutions cause an increase in the mobilities of π-electrons in the direction of the short molecular axis, but the β-substitutions lead to an increase in the direction of the long molecular axis.
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