Meta-Diethynylbenzene dianion

Meta-Diethynylbenzene dianion
	File:Image-Meta-diethynylbenzene dianion.png; Meta-diethynylbenzene dianion
	; The compound used for the synthesis of Meta-diethynylbenzene dianion
Names
	IUPAC name Meta-diethynylbenzene dianion
Properties
Chemical formula	C; 6H; 4C2−; 4
Hazards
	Occupational safety and health (OHS/OSH):
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). verify (what is ?) Infobox references

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 ( ${\ce {{C2H2}-}}$ ) 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

{\ce {\overset {}{C6H4(C3HO2)2->[{\ce {ESI}}][][C6H4(C3O2)2]^{2-}->[{\ce {CID}}][][C6H4(C5O2)]^{2-}->[{\ce {CID}}][][C6H4(C2)2]^{2-}}}}

The compound after the first stage of Collision Induced Dissociation having lost a Carbon dioxide molecule and retaining the negative charge.

The compound after the first stage of Collision Induced Dissociation having lost a Carbon dioxide molecule and retaining the negative charge.
${\ce {Meta-[C6H4(C5O2)]^{2-}}}$ is subjected through Collision Induced Dissociation for the second time losing another Carbon dioxide molecule but retaining the negative charge. Thus, the compound, Meta-diethynylbenzene dianion is formed.

${\ce {Meta-[C6H4(C5O2)]^{2-}}}$ is subjected through Collision Induced Dissociation for the second time losing another Carbon dioxide molecule but retaining the negative charge. Thus, the compound, Meta-diethynylbenzene dianion is formed.

Note: CID means Collision Induced Dissociation. ESI means Electrospray Ionization.

References

^[1]

^ 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.

[1] 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.

[1]

Meta-Diethynylbenzene dianion

Synthesis

Summary of the Synthesis

See also

List of the other isomers

References