Aromaticity and aminopyrroles: desmotropy and solution tautomerism of 1H-pyrrol-3-aminium and 1H-pyrrol-3(2H)-iminium cation: a stable σ-complex.
J Org Chem
; 78(3): 1107-12, 2013 Feb 01.
Article
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| MEDLINE
| ID: mdl-23272640
ABSTRACT
Protonation of 3-aminopyrrole at C-2 gave the σ-complex 1H-pyrrol-3(2H)-iminium cation, whereas protonation at the exoamino group gave its 1H-pyrrol-3-aminium tautomer. Both tautomers were isolated as their respective tetrakis(pentafluorophenyl)borate salt, an example of desmotropy. In solution, the NH(3)-tautomer was favored in hydrogen-bonding solvents and the CH(2)-tautomer in CH(2)Cl(2). A combination of effects on the aromaticity of the aminopyrrole ring increased the relative stability of the σ-complexes (conjugate acids) such that they can be readily observed or isolated.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2013
Tipo del documento:
Article
País de afiliación:
Estados Unidos