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Polycyano Derivatives of Some Cyclic and Polycyclic Hydrocarbons Provide Stable Anions and Dianions – A Density Functional Study

Peran, Nena; Despotović, Ines; Maksić, Zvonimir Polycyano Derivatives of Some Cyclic and Polycyclic Hydrocarbons Provide Stable Anions and Dianions – A Density Functional Study. In: Znanstveni susreti 3. vrste (7 July 2011 - 8 July 2011) Zagreb, Hrvatska. (Unpublished)

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The investigations of negatively charged molecular systems have been a subject matter of vivid research interest over decades. This is not surprizing, because mono- and multiple anions are ubiquitous in the living species and play an important role in chemistry, biochemistry and the solid state materials. In contrast to the situation occurring in the liquid solutions and solids, where anions are stabilized by the interactions with the environment, they are highly elusive in the gas phase (GP) due to electron repulsion. Building on our previous study, where it was shown that some cyanated radialenes are capable of forming dianions in the GP1, we are reporting on the results obtained in investigating some larger monocyclic and polycyclic organic compounds dressed by the CN and CF3 groups. For that purpose we have employed DFT–B3LYP/6-311+G(d) metod, which has been validated first on some experimentally known dianions. Subsequently, it was conclusively shown that alternating CF3 and CN substituents in cyclooctatetraene lead to its highly pronounced electron affinity. Moreover, its dianion is stable against the electron detachment. The latter is strongly enhanced in octacyanooctatetraene. The origin is identified in the aromaticity of the ring possessing 10p electron, which is additionaly vigorously supported by the anionic resonance with the CN groups. The same conclusions hold for 14 p electron dianions of biphenylene and dicyclobuteneoctatetraene fully cyanated by the 8 CN groups and some related systems. The present results might be important pertaining to the design of new organic materials exhibiting conductive properties. 1 I. Despotović, Z. B. Maksić, J. Mol. Struct. (Theochem), 2007, 811, 313-322.

Item Type: Unpublished conference/workshop items or lecture materials
Uncontrolled Keywords: mono- and multiple anions
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Nena Radić
Date Deposited: 18 Sep 2012 12:55

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