Quantum Chemical Studies on the Prototropic and Acid/Base Equilibria for 2-Aminopyrrole in Vacuo—Role of CH Tautomers in the Design of Strong Brønsted Imino N-Bases DOI Creative Commons
Ewa D. Raczyńska, Pierre‐Charles Maria, J. Gál

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(10), P. 2112 - 2112

Published: May 9, 2025

In the quest of pivotal origin very strong gas-phase proton basicity for some iminopyrrole derivatives, proposed in literature on basis quantum chemical calculations, full tautomeric and acid/base equilibria were investigated vacuo 2-aminopyrrole exhibiting enamino–imino tautomerism. Thermochemistry these processes at Density Functional Theory (DFT) level indicates a lower stability imino than enamino tautomers. However, N atom forms displays an exceptionally high basicity, particularly minor rare tautomers containing least one pyrrole C atom. This explains why derivatives CH (being free prototropy) display basicity. As predicted by Maksić group using methods, can be considered as good organic N-superbase candidates. Unfortunately, other structures (proposed same group) possess labile protons, and, thus, exhibit prototropy, resulting transformation into more stable but less basic aminopyrrole under synthesis conditions or measurements.

Language: Английский

Quantum Chemical Studies on the Prototropic and Acid/Base Equilibria for 2-Aminopyrrole in Vacuo—Role of CH Tautomers in the Design of Strong Brønsted Imino N-Bases DOI Creative Commons
Ewa D. Raczyńska, Pierre‐Charles Maria, J. Gál

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(10), P. 2112 - 2112

Published: May 9, 2025

In the quest of pivotal origin very strong gas-phase proton basicity for some iminopyrrole derivatives, proposed in literature on basis quantum chemical calculations, full tautomeric and acid/base equilibria were investigated vacuo 2-aminopyrrole exhibiting enamino–imino tautomerism. Thermochemistry these processes at Density Functional Theory (DFT) level indicates a lower stability imino than enamino tautomers. However, N atom forms displays an exceptionally high basicity, particularly minor rare tautomers containing least one pyrrole C atom. This explains why derivatives CH (being free prototropy) display basicity. As predicted by Maksić group using methods, can be considered as good organic N-superbase candidates. Unfortunately, other structures (proposed same group) possess labile protons, and, thus, exhibit prototropy, resulting transformation into more stable but less basic aminopyrrole under synthesis conditions or measurements.

Language: Английский

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