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Pyrrole is an extremely weak base for an amine, with a conjugate acid pK a of −3.8. The most thermodynamically stable pyrrolium cation (C 4 H 6 N +) is formed by protonation at the 2 position. Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethylpyrrole has a conjugate acid pK a of +3.7.
As reported by Matano and Imahori in 2008, a phosphaporphyrin is constructed with a phosphole linked to two pyrrole functional groups which is then bound to another pyrrole molecule. Specifically, addition of 2,5-bis(hydroxymethyl)-1-phenyl-1-thiophosphole to excess pyrrole in the presence of BF 3 ·OEt 2 results in the phosphatripyrrane precursor.
With a total of 26 π-electrons, of which 18 π-electrons form a planar, continuous cycle, the porphyrin ring structure is often described as aromatic. [2] [3] One result of the large conjugated system is that porphyrins typically absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored.
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Tetrapyrroles are a class of chemical compounds that contain four pyrrole or pyrrole-like rings. The pyrrole/pyrrole derivatives are linked by (= (CH)-or -CH 2-units), in either a linear or a cyclic fashion. Pyrroles are a five-atom ring with four carbon atoms and one nitrogen atom.
Examples of non-basic nitrogen-containing aromatic rings are pyrrole and indole. In the oxygen- and sulfur-containing aromatic rings, one of the electron pairs of the heteroatoms contributes to the aromatic system (similar to the non-basic nitrogen-containing rings), whereas the second lone pair extends in the plane of the ring (similar to the ...
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The structure of the molecule can be described as molecule of pyrrole with sidechains substituted for hydrogen atoms at positions 2, 3 and 4 in the ring (1 being the nitrogen atom); respectively, an aminomethyl group −CH 2 −NH 2, an acetic acid (carboxymethyl) group −CH 2 −COOH, and a propionic acid (carboxyethyl) group −CH 2 −CH 2 ...