Meso-Octamethylporphyrinogen Explained

meso-Octamethylporphyrinogen, usually referred to simply as octamethylporphyrinogen, is an organic compound with the formula (Me2C-C4H2NH)4 (Me = CH3. It is one of the simplest porphyrinogens, a family of compounds that occur as intermediates in the biosynthesis of hemes and chlorophylls. In contrast to those rings, porphyrinogens are colorless since they lack extended conjugation. The prefix meso-octamethyl indicates that the eight methyl groups are located on the carbon centers that interconnect the four pyrrole rings. Also unlike porphyrins, the porphyrinogens are highly ruffled.[1]

Preparation

The compound was first reported by Adolph Bayer.[2] It is made by condensation of pyrrole with acetone.[3]

Reactions

The pyrrolic N-H centers of ctamethylporphyrinogen can be deprotonated, and the resulting tetraanion functions as a tetradentate ligand for a variety of metal ions.[4]

References

  1. 10.1039/A706280J. Calixpyrroles. 1998. Gale. Philip A.. Sessler. Jonathan L.. Král. Vladimír. Chemical Communications. 1–8.
  2. 10.1002/cber.188601902121. Ueber ein Condensationsproduct von Pyrrol mit Aceton. 1886. Baeyer. Adolf. Berichte der Deutschen Chemischen Gesellschaft. 19. 2. 2184–2185.
  3. 10.1021/ed082p618. Synthesis of Meso-Octamethylporphyrinogen: An Undergraduate Laboratory Mini-Scale Experiment in Organic Heterocyclic Chemistry. 2005. Sobral. Abilio J.F.N.. Journal of Chemical Education. 82. 4. 618. 2005JChEd..82..618S.
  4. 10.1021/ic0616636. Ground- and Excited-State Reactivity of Iron Porphyrinogens. 2007. Bachmann. Julien. Hodgkiss. Justin M.. Young. Elizabeth R.. Nocera. Daniel G.. Inorganic Chemistry. 46. 3. 607–609. 17256999.