Chemistry:Para-Diethynylbenzene dianion

Para-Diethynylbenzene dianion

Names
IUPAC name Para-diethynylbenzene dianion
Properties
Chemical formula	C6H4C2−4
Identifiers
3D model (JSmol)	Interactive image
InChI InChI=1S/C10H4/c1-3-9-5-7-10(4-2)8-6-9/h5-8H/q-2 Key: GGQMWKMAMDPRPA-UHFFFAOYSA-N
SMILES [C-]#Cc1ccc(cc1)C#[C-]
Hazards
Main hazards	Extremely corrosive
Related compounds
Related bases	Meta-diethynylbenzene dianion Ortho-diethynylbenzene dianion Lithium monoxide anion
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

para-Diethynylbenzene dianion is the third strongest base ever synthesized. It is an isomer of ortho-diethynylbenzene dianion, as well as of meta-diethynylbenzene dianion.

Each of the ethynyl groups in Para-diethynylbenzene dianion has a negative charge. Para-diethynylbenzene dianion has no known use yet. It has two isomers: Meta-diethynylbenzene dianion and Ortho-diethynylbenzene dianion All of these isomers including Para-diethynylbenzene dianion exist in the gas phase, contrary to the normal bases (such as the hydroxide anion) which exists in the solution state.

Synthesis

Step 1

C₆H₄(C₃HO₂)₂is the parent compound. In the next step, the parent compound is ionized (i.e., the two hydrogen atoms from the two carboxylic acid groups (which is attached to the carbon atom of the ethyne group, while the ethyne group is further attached to the benzene group)).

Step 2

The ionized parent compound [C₆H₄(C₃O₂)₂]²⁻ is subjected to collisional activation, because of which, one of the carboxylate anion loses a carbon dioxide molecule.

Step 3

The ionized parent compound is again subjected to collisional activation, because of which, the other carboxylate anion loses the other carbon dioxide molecule.

Step 4

Therefore, the Para-diethynylbenzene dianion [C₆H₄(C₂)₂]²⁻ is formed, having lost, in total, 2 Hydrogen atoms and 2 molecules of Carbon dioxide.

This is the reaction through which the researchers in Australia created the super base.

Summary of the reaction

[math]\ce{ C6H4(C3HO2)2 -> {[C6H4(C3O2)2]}^{2-} -> {[C6H4(C5O2)]}^{2-} -> {[C6H4(C2)2]}^{2-} }[/math]

Although the process of synthesizing the Para-diethynylbenzene dianion is the same as the process of synthesizing Ortho-diethynylbenzene dianion, the only difference is that the parent compound [C₆H₄(C₃HO₂)₂] is a different isomer, different than that of Ortho-diethynylbenzene dianion.

References

http://pubs.rsc.org/en/content/articlehtml/2016/sc/c6sc01726f

See also

• Lithium monoxide anion