Diethynylbenzene dianion

Diethynylbenzene dianion
Identifiers
3D model (JSmol)	(ortho): Interactive image; (meta): Interactive image; (para): Interactive image;
	InChI (para): InChI=1S/C10H4/c1-3-9-5-7-10(4-2)8-6-9/h5-8H/q-2 Key: GGQMWKMAMDPRPA-UHFFFAOYSA-N;
	SMILES (ortho): [C-]#Cc0ccccc0C#[C-]; (meta): [C-]#Cc0cccc(c0)C#[C-]; (para): [C-]#Cc1ccc(cc1)C#[C-];
Properties
Chemical formula	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

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. 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). The meta isomer is the second-strongest, and the para isomer is the third-strongest.

Identifiers

3D model (JSmol)	(ortho): Interactive image (meta): Interactive image (para): Interactive image
InChI (para): InChI=1S/C10H4/c1-3-9-5-7-10(4-2)8-6-9/h5-8H/q-2 Key: GGQMWKMAMDPRPA-UHFFFAOYSA-N
SMILES (ortho): [C-]#Cc0ccccc0C#[C-] (meta): [C-]#Cc0cccc(c0)C#[C-] (para): [C-]#Cc1ccc(cc1)C#[C-]
Properties
Chemical formula	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