Inorganic chemistry, bilane is a compound with the formula C19H20N4or[(C4H4N)−CH2−(C4H3N)−]2CH2. It is a tetrapyrrole, a class of compounds with four independent pyrrole rings. Specifically, the molecule can be described as four pyrrole molecules C4H5N connected in an open chain by three methylene bridges−CH2−atcarbons adjacent to the nitrogens, replacing the respective hydrogens.[1]
The name is also used for the class of compounds formally derived from bilane proper by replacement of some additional hydrogen atoms by various functional groups. Natural bilanes usually have side chains substituted on the two carbons in each pyrrole ring that are not adjacent to the nitrogens. Artificial bilanes may be substituted on the bridging carbons (called meso positions).[2]
The parent (unsubstituted) bilane is difficult to prepare and unstable,[3] but substituted derivatives are synthesized by most living organisms as intermediates in the synthesis of natural porphyrins. Substituted bilanes may also be the starting point for the synthesis of artificial porphyrins.[2][3]
^ abcLindsey, J. S. (2010). "Synthetic Routes to meso-Patterned Porphyrins". Accounts of Chemical Research. 43 (2): 300–311. doi:10.1021/ar900212t. PMID19863076.
^ abClaudia Ryppa, Mathias O. Senge, Sabine S. Hatscher, Erich Kleinpeter, Philipp Wacker, Uwe Schilde, and Arno Wiehe (2005): "Synthesis of Mono‐ and Disubstituted Porphyrins: A‐ and 5,10‐A2‐Type Systems". Chemistry, A European Journal, volume 11, issue 11, pages 3427-3442. doi:10.1002/chem.20050000
