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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.
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The Barton–Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanide under basic conditions. [1] It is named after Derek Barton and Samir Zard who first reported it in 1985.
Calculations suggest that whereas pyrrole (C 4 H 4 NH) molecule is planar, phosphole (C 4 H 4 PH) and heavier metalloles are not, and their pnictogen-bonded hydrogen atom extends out of plane. [9] A similar tendency is predicted for the fluorinated C 4 F 4 MH derivatives (M = N, P, As, ..), but the inversion barriers are about 50–100% higher.
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