Porphine

Chemical compound From Wikipedia, the free encyclopedia

Porphine or porphin is an organic compound of empirical formula C20H14N4. It is heterocyclic and aromatic. The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles.[2]

Quick facts Names, Identifiers ...
Porphine
Names
IUPAC name
Porphyrin[1]
Other names
Porphin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.690 Edit this at Wikidata
UNII
  • InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12- checkY
    Key: RKCAIXNGYQCCAL-CEVVSZFKSA-N checkY
  • InChI=1/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-
    Key: RKCAIXNGYQCCAL-CEVVSZFKBA
  • C1=CC2=CC5=CC=C(C=C4C=CC(C=C3C=CC(=CC1=N2)N3)=N4)N5
Properties
C20H14N4
Molar mass 310.35196 g/mol
Appearance Dark red, shiny leaflets
Melting point N/A
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble.[3] As a result, porphine is mostly of theoretical interest. It has been detected in GC-MS of certain fractions of Piper betle.[4]

Porphine derivatives: porphyrins

Further information: Porphyrin

Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX.[5] Many synthetic porphyrins are also known, including octaethylporphyrin[6] and tetraphenylporphyrin.[7]

  • Common porphyrins
  • Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
    Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
  • Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical.
    Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical.
  • Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methine centers are occupied by phenyl groups.
    Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methine centers are occupied by phenyl groups.
Two resonance structures of porphine.

Further reading

  • Budavari, Susan (1989). "7758. Porphine". The Merck Index (11th ed.). Merck & Co., Inc. p. 1311. ISBN 0-911910-28-X. LCCN 89-60001.

References

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