Pentacyanocyclopentadiene

Structural formula
General
Surname	Pentacyanocyclopentadiene
Molecular formula	C 10 HN 5
External identifiers / databases
Wikidata	Q2069306
properties
Molar mass	191.1 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pentacyanocyclopentadiene is a cyclic carbon compound . It contains five cyano groups (–CN) and two double bonds in the molecule , which is why it belongs to the cycloalkadienes .

The cyano group is also the functional group of this compound. Due to the relatively non-polar character of pentacyanocyclopentadiene, it is not soluble in water. The five cyano groups and the formation of an aromatic system (as in the parent compound cyclopentadiene ) stabilize the anion (by dissociating the H ⁺ ) in such a way that it is an extremely strong acid.

After deprotonation, the anion of pentacyanocyclopentadiene is mesomeric stabilized.

It has an extremely low pKa value of <−11. Such a value does not reach a mineral acid such as sulfuric acid (pK _s value = -3.0), pentacyanocyclopentadiene therefore, by definition, to the Super acids is counted.

swell

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

literature

Vianello R et al. (2004): In search of ultrastrong Brønsted neutral organic superacids: a DFT study on some cyclopentadiene derivatives. Chemistry 10 (22); 5751-60; PMID 15484200

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.