Meta-Diethynylbenzene dianion

Meta-Diethynylbenzene dianion

File:Image-Meta-diethynylbenzene dianion.png Meta-diethynylbenzene dianion
The compound ${\ce {C6H4(C3HO2)2}}$ 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). N verify (what is YN ?) 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.

See also

• Lithium monoxide anion
• Superbases
• Collision-induced dissociation
• Electrospray ionization

List of the other isomers

• Ortho-diethynylbenzene dianion
• Para-diethynylbenzene dianion