''para''-Diethynylbenzene dianion
| Names | |
|---|---|
| IUPAC name
Para-diethynylbenzene dianion | |
| Properties | |
| C 6H 4C2− 4 | |
| Identifiers | |
3D model (JSmol) |
|
| |
| |
| Hazards | |
| Main hazards | Extremely corrosive |
| Related compounds | |
Related bases |
Meta-diethynylbenzene dianion |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
  | |
| Infobox references | |
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
![{\displaystyle {\ce {C6H4(C3HO2)2 -> {[C6H4(C3O2)2]}^{2-}-> {[C6H4(C5O2)]}^{2-}-> {[C6H4(C2)2]}^{2-}}}}](../I/m/098f63fbff536352d668a7a5eba9edbb7777c823.svg)
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