What is it about?
A series of nine α-nitroso pyrroles containing thienyl moieties have been synthesized, characterized and studied by spectroscopic and crystallographic techniques. Variable-temperature NMR reveals an equilibrium between nitroso and oxime forms and we presented the first crystal structures of oxime tautomers in alpha-nitroso thienylpyrroles, which are stabilized by resonance-assisted hydrogen bonds (RAHBs).
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Why is it important?
Tautomerism plays a fundamental role in chemical reactivity, molecular recognition, and hydrogen bonding networks, influencing the stability and properties of many functional molecules. This study underscores how supramolecular synthons and RAHBs influence tautomerism in heterocyclic systems, redefine the structural landscape of nitroso-pyrroles and open new perspectives for their reactivity and potential applications in organic synthesis and materials science.
Perspectives
Writing this article was a truly rewarding experience, as it allowed me to deepen my understanding of crystal structures and their resolution. I also hope the reader finds it engaging, as it presents the story of the first crystallographic evidence of an oxime tautomer in pyrroles.
Mónica Farfán-Paredes
Centro de Investigación y de Estudios Avanzados del IPN
Read the Original
This page is a summary of: Nitroso-oxime tautomerism in nitroso pyrroles: Revealing spectral properties and crystalline structure, Journal of Molecular Structure, November 2025, Elsevier,
DOI: 10.1016/j.molstruc.2025.142956.
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