Peer-reviewedCC BY-NC 4.0Chemical Science
The crystalline radical anion salt of a free N-heterocyclic carbene
Abstract
Radical ions of free N-heterocyclic carbenes (NHCs) have remained short-lived, mostly elusive, intermediates so far. We probed the square schemes for proton-coupled electron transfers of representative redox-active free NHCs. We found that NHC radical anions NHC˙− and/or the conjugated acid NHC·H˙ could be persistent. In the case of a benzoquinone-based NHC, both radical forms were isolated as stable crystalline compounds, characterized, including by single-crystal X-ray diffraction studies, and were engaged in the straightforward divergent syntheses of NHC-based radicals.
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BibTeX
@article{smits2026crystalline,
title = {{The crystalline radical anion salt of a free N-heterocyclic carbene}},
author = {Preslav Smits and Jacques Pecaut and Christian Philouze and Jérome Fortage and Eder Tomás-Mendivil and David Martin},
journal = {Chemical Science},
year = {2026},
month = aug,
doi = {10.1039/d6sc05617b},
url = {https://hal.science/hal-05759926v1},
note = {CC BY-NC 4.0},
}
RIS
TY - JOUR
TI - The crystalline radical anion salt of a free N-heterocyclic carbene
AU - Preslav Smits
AU - Jacques Pecaut
AU - Christian Philouze
AU - Jérome Fortage
AU - Eder Tomás-Mendivil
AU - David Martin
PY - 2026
DA - 2026/08/06
JO - Chemical Science
DO - 10.1039/d6sc05617b
UR - https://hal.science/hal-05759926v1
AB - Radical ions of free N-heterocyclic carbenes (NHCs) have remained short-lived, mostly elusive, intermediates so far. We probed the square schemes for proton-coupled electron transfers of representative redox-active free NHCs. We found that NHC radical anions NHC˙− and/or the conjugated acid NHC·H˙ could be persistent. In the case of a benzoquinone-based NHC, both radical forms were isolated as stable crystalline compounds, characterized, including by single-crystal X-ray diffraction studies, and were engaged in the straightforward divergent syntheses of NHC-based radicals.
SN - 2041-6520
SN - 2041-6539
ER -