meta-Diethynylbenzene dianion

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Meta-Diethynylbenzene dianion
Image-Meta-diethynylbenzene dianion.png
Meta-diethynylbenzene dianion
Meta-diethynylbenzene dianion precursor compound (main picture).png
The compound C
6
H
4
(C
3
HO
2
)
2
used for the synthesis of Meta-diethynylbenzene dianion
Names
IUPAC name
Meta-diethynylbenzene dianion
Properties
C
6
H
4
C2−
4
Hazards
Main hazards Extremely corrosive
Related compounds
Related bases
Ortho-diethynylbenzene dianion

Para-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).
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Infobox references

The meta-diethynylbenzene dianion is a structural isomer of the ortho-diethynylbenzene dianion. The meta-diethynylbenzene dianion is not as strong as ortho-diethynylbenzene dianion, but it is still the second-strongest superbase. Like the ortho-diethynylbenzene dianion, the meta-diethynylbenzene dianion exists in the gas state, contrary to the other bases and superbases which exist in the solution state. In the meta-diethynylbenzene dianion, the two negatively charged ethynyl (−C
2
H
2
) groups are bonded to the first and third carbon atoms of the benzene ring. But in the ortho-diethynylbenzene dianion, the ethynyl groups are bonded to the first and second carbon atoms of the benzene ring. Like Ortho-diethynylbenzene dianion, Meta-diethynylbenzene dianion has no known use.

Synthesis[edit]

Step 1
A sample of meta-C6H4(C3HO2)2 is taken.
Step 2
In this next step, the parent compound is subjected through electrospray ionization (ESI) and consequently, loses two Hydrogen atoms and therefore, acquires a charge of −2. The new compound's chemical formula is [C6H4(C3O2)2]2−
Step 3
The ionized parent compound [C6H4(C3O2)2]2− is subjected to collision-induced dissociation (CID), because of which, one of the carboxylate anion loses a Carbon dioxide molecule to become [C6H4(C5O2)]2−.
Step 4
The meta-[C6H4(C3O2)2]2− compound is again subjected to collision-induced dissociation, because of which, the other carboxylate anion loses the other Carbon dioxide molecule and becomes meta-[C6H4(C5O2)]2−
Step 5
Therefore, the meta-diethynylbenzene dianion [C6H4(C2)2]2− is formed, having lost, in total, two hydrogen atoms and two molecules of carbon dioxide.

The same process can generate either ortho-diethynylbenzene dianion and Meta-diethynylbenzene dianion depending on which isomer of the original compound is used.

Summary[edit]

See also[edit]

List of the other isomers[edit]

References[edit]

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). doi:10.1039/C6SC01726F. Retrieved 12 January 2018.