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Distonic biradical anions. Synthesis and characterization of the 3,5-dehydrophenyl and 1,3,5-trimethylenebenzene negative ions

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/ja960756r· OSTI ID:282947
;  [1]
  1. Purdue Univ., West Lafayette, IN (United States)

We recently described a new method for producing intense beams of structurally-defined biradical negative ions (`distonic radical anions`) in the gas phase based on reactions between trimethylsilyl-substituted carbanions and molecular fluorine. We now wish to report the extension of this procedure to the rational synthesis of negative ions of triradicals, i.e., `distonic biradical anions.` The significance of these species is manifold. Polyradicals and their associated ions are the central focus of current efforts to produce synthetic organic ferromagnets. In this report, we describe the gas-phase synthesis and characterization of 3,5-dehydrophenyl anion, 1, and 1,3,5-trimethylenebenzene negative ion, 2. Ion 1 corresponds to the negative ion of the ({sigma},{sigma},{sigma}) triradical 1,3,5-benzenetriyl, and it can also be viewed as a deprotonated m-benzyne. 29 refs.

OSTI ID:
282947
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 24 Vol. 118; ISSN JACSAT; ISSN 0002-7863
Country of Publication:
United States
Language:
English

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