Crystal and molecular structure of the isobacteriochlorin: (2,3,7,8-tetrahydro-5,10,15,20-tetraphenylporphinato)(pyridine)zinc(II) benzene solvate

Journal Article · Wed Jan 14 04:00:00 EST 1981 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00391a031· OSTI ID:6612614

Barkigia, K M; Fajer, J; Spaulding, L D; Williams, G J.B.

The structure of the isobacteriochlorin, (2,3,7,8-tetrahydro-5,10,15,20-tetraphenylporphinato)(pyridine)zinc(II) benzene solvate, has been determined by three-dimensional x-ray diffraction. The compound crystallizes with one molecule each of benzene and reduced porphyrin per asymmetric unit in the triclinic space group P anti 1 with a = 11.452 (5) A, b = 13.332 (4) A, c = 14.718 (6) A, ..cap alpha.. = 99.05 (2)/sup 0/, ..beta.. = 94.37 (4)/sup 0/, and ..gamma.. = 104.88 (4)/sup 0/. It is isomorphous with the corresponding chlorin, (2,3-dihydrotetraphenylporphinato)(pyridine)zinc(II) benzene solvate. The structure has been refined by least squares in three matrix blocks to R/sub F/ = 0.073, on the basis of 6217 reflections with F/sub 0/ > 0. The results unambiguously confirm the structure, previously deduced by spectroscopic techniques, for the general class of isobacteriochlorins (and for siroheme, the prosthetic group of nitrite and sulfite reductases) as prophyrins in which two adjacent pyrrole rings are reduced. In addition, the data indicate that successive saturation of the pyrrole rings in prophyrins, chlorins, and isobacteriochlorins exerts no major effect on the stereochemistry of the macrocycles and suggest that the geometric details of high spin iron siroheme will not deviate substantially from those of iron(III) porphyrins.

• Research Organization: Brookhaven National Lab., Upton, NY
• DOE Contract Number: AC02-76CH00016
• OSTI ID: 6612614
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 103:1; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
BENZENE
BOND ANGLE
BOND LENGTHS
CARBOXYLIC ACIDS
COHERENT SCATTERING
COMPLEXES
CRYSTAL LATTICES
CRYSTAL STRUCTURE
DIFFRACTION
DIMENSIONS
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
LENGTH
MOLECULAR STRUCTURE
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PORPHYRINS
SCATTERING
TRICLINIC LATTICES
X-RAY DIFFRACTION
ZINC COMPLEXES