2001
DOI: 10.1021/jp013524+
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The Anion Radical of [18]Annulene

Abstract: The anion radicals of [18]annulene and of [6]annulene undergo Jahn−Teller distortions from the D 6 h conformations of their respective neutral molecules. The conformation of lowest energy for the anion radical of benzene has a C2 v symmetry, and that for the anion radical of [18]annulene is D 2 h . The very rapid pseudo-rotation of the benzene C2 v system causes the six protons of the benzene anion radical to appear as if they were equivalent in the EPR experiment. Fast pseudo-rotation rendering the uni… Show more

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Cited by 10 publications
(8 citation statements)
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References 19 publications
(44 reference statements)
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“…The remaining five carbons, on the other side of the nodal carbons, are twisted from planarity. Hence, the di -trans -C 12 H 12 anion radical undergoes pseudorotation around a “Mexican hat” in a manner that is analogous to that found in the benzene and [18]annulene systems …”
mentioning
confidence: 80%
See 1 more Smart Citation
“…The remaining five carbons, on the other side of the nodal carbons, are twisted from planarity. Hence, the di -trans -C 12 H 12 anion radical undergoes pseudorotation around a “Mexican hat” in a manner that is analogous to that found in the benzene and [18]annulene systems …”
mentioning
confidence: 80%
“…As in the case of the [18]annulene anion radical,11b the pseudorotation is not fast on the EPR time scale, and the structure and spin densities oscillate as shown in Scheme .
5
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mentioning
confidence: 92%
“…The radical anion of 6 was first observed by Sondheimer [87] and recently by Stevenson [88]. The main conclusion from these studies is that the structure is nonplanar, because of a Jahn-Teller distortion.…”
Section: [18]annulenementioning
confidence: 88%
“…Conjugate polymers as a research of great contention give the probability to realize the Gentile particle model. To be specific, we wish to show that cyclic hydrocarbon polyenes can be viewed as a realization of Gentile systems. Cyclic hydrocarbon polyenes, or simply N -annulenes, C N H N , denote the family of organic molecules that are monocyclic unsaturated hydrocarbons. The electron paramagnetic resonance, , aromaticity, and fluorescence property are well investigated in the annulene systems. The Hückel model, a simple but effective molecular orbital model for describing planar conjugated molecules, will be used to deal with N -annulenes.…”
Section: Introductionmentioning
confidence: 99%
“…Cyclic hydrocarbon polyenes, or simply N-annulenes, C N H N , denote the family of organic molecules that are monocyclic unsaturated hydrocarbons. 20−23 The electron paramagnetic resonance, 24,25 aromaticity, 26 and fluorescence property 27 are well investigated in the annulene systems. The Huckel model, a simple but effective molecular orbital model for describing planar conjugated molecules, 28−31 will be used to deal with N-annulenes.…”
Section: Introductionmentioning
confidence: 99%