2-Aminopyrrole and simple 1-substituted 2-aminopyrroles

Preparation and ab initio study on the effect of solvent on the amino-imino tautomeric equilibrium

Michael De Rosa, Roy P. Issac, Manuel Marquez, Modesto Orozco, Francisco J. Luque, Mark D. Timken

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

This work describes the preparation and NMR characterization of 2-aminopyrrole and simple 1-substituted-2-aminopyrroles without further substitution on the ring. The question of the effect of solvent on tautomerism in 2-aminopyrroles has been studied by using ab initio quantum mechanical methods. Theoretical calculations indicated that 2-aminopyrrole is the most stable form in chloroform and in water. Experimentally this is what was observed. Calculations indicated that in the case of the 1-methyl-2-aminopyrrole both amino and imino tautomers should be observable in water.

Original languageEnglish (US)
Pages (from-to)1433-1437
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number7
StatePublished - Jul 1 1999

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Water
Chloroform
Substitution reactions
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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abstract = "This work describes the preparation and NMR characterization of 2-aminopyrrole and simple 1-substituted-2-aminopyrroles without further substitution on the ring. The question of the effect of solvent on tautomerism in 2-aminopyrroles has been studied by using ab initio quantum mechanical methods. Theoretical calculations indicated that 2-aminopyrrole is the most stable form in chloroform and in water. Experimentally this is what was observed. Calculations indicated that in the case of the 1-methyl-2-aminopyrrole both amino and imino tautomers should be observable in water.",
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2-Aminopyrrole and simple 1-substituted 2-aminopyrroles : Preparation and ab initio study on the effect of solvent on the amino-imino tautomeric equilibrium. / De Rosa, Michael; Issac, Roy P.; Marquez, Manuel; Orozco, Modesto; Luque, Francisco J.; Timken, Mark D.

In: Journal of the Chemical Society. Perkin Transactions 2, No. 7, 01.07.1999, p. 1433-1437.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 2-Aminopyrrole and simple 1-substituted 2-aminopyrroles

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AU - De Rosa, Michael

AU - Issac, Roy P.

AU - Marquez, Manuel

AU - Orozco, Modesto

AU - Luque, Francisco J.

AU - Timken, Mark D.

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