Global InformationDiethynylbenzene dianion information
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3D model (JSmol)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C10H42− |
| Molar mass | 124.143 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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In organic chemistry, a diethynylbenzene dianion is an anion consisting of two ethynyl anions as substituents on a benzene ring. With the chemical formula C
6H
4C2−
4, three positional isomers are possible, differing in the relative positions of the two substituents around the ring:
- ortho-diethynylbenzene dianion
- meta-diethynylbenzene dianion
- para-diethynylbenzene dianion
The gaseous state of all three anions are of theoretical interest. They have been generated by decarboxylation of benzene dipropynoic acids, using the technique of mass spectrometry.[1][2] The three isomers of the dianion are the three strongest known superbases ever, with the ortho isomer being the strongest, with a proton affinity of 1,843.987 kJ/mol (440.723 kcal/mol).[1] The meta isomer is the second-strongest, and the para isomer is the third-strongest.
- ^ a b Poad, Berwyck L. J.; Reed, Nicholas D.; Hansen, Christopher S.; Trevitt, Adam J.; Blanksby, Stephen J.; Mackay, Emily G.; Sherburn, Michael S.; Chan, Bun; Radom, Leo (12 January 2018). "Preparation of an ion with the highest calculated proton affinity: ortho-diethynylbenzene dianion". Chemical Science. 7 (9): 6245–6250. doi:10.1039/C6SC01726F. PMC 6024202. PMID 30034765.
- ^ Bergius, Will (19 July 2016). "Basically record breaking". Chemistry World. Archived from the original on 2 June 2023. Retrieved 17 October 2018.