Meta-Diethynylbenzene dianion
File:Image-Meta-diethynylbenzene dianion.png Meta-diethynylbenzene dianion
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![]() The compound used for the synthesis of Meta-diethynylbenzene dianion
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Names | |
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IUPAC name
Meta-diethynylbenzene dianion
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Properties | |
C 6H 4C2− 4 | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Extremely corrosive |
Related compounds | |
Related bases
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Ortho-diethynylbenzene dianion |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Meta-diethynylbenzene dianion is a structural isomer of Ortho-diethynylbenzene dianion. Meta-diethynylbenzene dianion is not as strong as Ortho-diethynylbenzene dianion, but it still is the second strongest superbase. Like Ortho-diethynylbenzene dianion, Meta-diethynylbenzene dianion exists in the gas state, contrary to the other bases and superbase which exist in the solution state. In Meta-diethynylbenzene dianion, the two negatively charged ethynyl () groups are bonded to the first and third carbon atoms of the benzene ring. But in 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
- 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, 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, 2 Hydrogen atoms and 2 molecules of Carbon dioxide.
The same process can generate either Orthodiethynylbenzene dianion and Meta-diethynylbenzene dianion depending on which isomer of the original compound is used.
Summary of the Synthesis
Note: CID means Collision Induced Dissociation. ESI means Electrospray Ionization.
See also
List of the other isomers
References
- ^ 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.