Diethynylbenzene dianion
Group of isomeric chemical compounds which are strong bases / From Wikipedia, the free encyclopedia
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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
Names | |
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IUPAC name
2,4-Phenyldiethynediide | |
Systematic IUPAC name
Ethynidylphenylacetylide | |
Identifiers | |
3D model (JSmol) |
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Properties | |
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).
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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.