ArticleAngewandte Chemie (International ed. in English)2025
Exploring Mesoionic Imine-Carbodiimide (MII-CDI) Adducts: 1,3 H-Shift, N(I) Compounds and Guanidinate-Type Ligands.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Mesoionic N-Heterocyclic Olefins, Imines, Thiones, Phosphinidenes and Their Application in Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Exploring Mesoionic Imine-Carbodiimide (MII-CDI) Adducts: 1,3 H-Shift, N(I) Compounds and Guanidinate-Type Ligands.Angewandte Chemie (International ed. in English) · 2025Article
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5 authors.
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Abstract
In this study, we report our recent findings on the synthesis and reactivity of a novel 1,2,3-triazolin-5-imine-type mesoionic imine-carbodiimide (MII-CDI) adduct. Unlike reported NHC-CDI adducts, formed by the reactions of N-heterocyclic carbene (NHC) with CDI, these zwitterionic compounds undergo a spontaneous 1,3-hydrogen shift (1,3-H shift), resulting in guanidine-type compounds. The mechanism of this 1,3-H shift has been investigated through quantum chemical calculations. The MII-CDI adduct serves as a valuable synthon for the synthesis of mesoionic carbene-acyclic diamino carbene (MIC-ADC)-based nitreone (N(I)) compounds. We have conducted a detailed investigation into the electronic properties, chemical reactivity, and electrochemical behavior of these nitreone (N(I)) compounds. Additionally, the potential of these MII-CDI adducts as guanidinate ligands is explored. Our investigations here display the distinct reactivities of MII in contrast to their N-heterocyclic imine (NHI) congeners.
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