Surface‐Driven Keto–Enol Tautomerization: Atomistic Insights into Enol Formation and Stabilization Mechanisms

Abstract

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1,1‐Ethenediol: The Long Elusive Enol of Acetic Acid

“…Schauermann et al. reported the synthesis of the enol of acetophenone on metal surfaces stabilized by intermolecular interactions with the keto form of a second molecule to give a ketone‐enol dimer . Turecek et al .…”

“…[29] Schauermann et al reported the synthesis of the enol of acetophenone on metal surfaces stabilized by intermolecular interactions with the keto form of a second molecule to give a ketone-enol dimer. [34] Turecek et al [26] generated the enol of g-butyrolactone in the gas phase and characterized it by neutralization-reionization mass spectrometry. They found that the lactone enol persists as an isolated molecule in the gas phase.…”

1,1‐Ethendiol – Das lange Zeit schwer fassbare Enol der Essigsäure

“…beschrieben die Darstellung des Enols von Acetophenon auf Metalloberflächen. Das Enol wird hierbei durch eine intermolekulare Wechselwirkung mit einem zweiten Molekül Acetophenon in Form eines Keto‐Enol Dimers stabilisiert . Turecek et al .…”

“…Das Enol wird hierbei durch eine intermolekulare Wechselwirkung mit einem zweiten Molekül Acetophenon in Form eines Keto-Enol Dimers stabilisiert. [34] Turecek et al [26] konnten das Enol von g-Butyrolacton in der Gasphase darstellen und Enole kçnnten ebenfalls eine Rolle in der Chemie des interstellaren Mediums spielen. Diese Hypothese wird durch die Entdeckung von Ethenol (5) im Jahr 2001 in Sagittarius B2 anhand von Mikrowellenemissionen bekräftigt.…”

Disordered Two-Dimensional Self-Organization of Ethyl Pyruvate Molecules on the Pt(111) Surface

“…2−4 One obvious reason is the influence of the surface on each single adsorbed molecule, steric or electronic or by strong local electric fields, 5 leading to intramolecular changes, as for example, in surface-driven ketoenol tautomerization. 6 However, intermolecular interactions between several surface-adsorbed molecules are also clearly important, as demonstrated by ligand-directed heterogeneous catalysis. 7,8 Hence, molecular interaction and self-assembly on (metal) surfaces 9−11 is not only a research field on its own, ranging from investigations of interaction modes 12,13 to two-dimensional crystal engineering 14 but also an important ingredient for onsurface synthesis and heterogeneous catalysis.…”