The Radical Anions and Trianions of 1,8-Diphenylnaphthalene and of Some of its Derivatives Containing a Cyclophane Substructure
| Autor: | Fritz Vögtle, Fabian Gerson, Reinhart Möckel, René Heckendorn |
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| Rok vydání: | 1985 |
| Předmět: |
education.field_of_study
Bicyclic molecule Stereochemistry Organic Chemistry Population Biochemistry Catalysis Inorganic Chemistry Crystallography chemistry.chemical_compound chemistry Drug Discovery Molecule Moiety Physical and Theoretical Chemistry education Benzene Hyperfine structure Cyclophane Naphthalene |
| Zdroj: | Helvetica Chimica Acta. 68:1923-1932 |
| ISSN: | 0018-019X |
| Popis: | The radical anions of 1,8-diphenylnaphthalene (1) and its decadeuterio-(D10-1) and dimethyl-(2) derivatives, as well as those of [2.0.0] (1,4)benzeno(1,8)naphthaleno(1,4)benzenophane (3) and its olefinic analogue (4) have been studied by ESR and ENDOR spectroscopy, At a variance with a previous report, the spin population in and is to a great extent localized in the naphthalene moiety. A similar spin distribution is found for and . The ground conformations of - are chiral of C2 symmetry. For , an energy barrier between these conformations and the angle of twist about the bonds linking the naphthalene moiety with the phenyl substituents were estimated as ca. 50 kJ/mol and ca. 45°, respectively. The radical trianions of 1, D10-1, and 2, have also been characterized by their hyperfine data. In and , the bulk of the spin population resides in the two benzene rings so that these radical trianions can be regarded as the radical anions of ‘open-chain cyclophanes’ with a fused naphthalene π-system bearing almost two negative charges. The main features of the spin distribution in both and are correctly predicted by an HMO model of 1. |
| Databáze: | OpenAIRE |
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