Evidence map›Paper›PMID 39256544›Full record

ArticleNature chemistry2024

Isolation of a NHC-stabilized heavier nitrile and its conversion into an isonitrile analogue.

Martin E Doleschal, Arseni Kostenko, Jin Yu Liu, Shigeyoshi Inoue

Abstract read
In one paragraph

Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

6 citing papers in PubMed.

  1. Isolation and Reactivity of a Stannabismuthene.Angewandte Chemie (International ed. in English) · 2026
    Article
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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors.

Martin E DoleschalTUM School of Natural Sciences, Department of Chemistry, Catalysis Research Center and Wacker Institute of Silicon Chemistry, Technische Universität Müchen, Garching, Germany.
Arseni KostenkoTUM School of Natural Sciences, Department of Chemistry, Catalysis Research Center and Wacker Institute of Silicon Chemistry, Technische Universität Müchen, Garching, Germany.ORCID http://orcid.org/0000-0002-9593-4468
Jin Yu LiuTUM School of Natural Sciences, Department of Chemistry, Catalysis Research Center and Wacker Institute of Silicon Chemistry, Technische Universität Müchen, Garching, Germany.
Shigeyoshi InoueTUM School of Natural Sciences, Department of Chemistry, Catalysis Research Center and Wacker Institute of Silicon Chemistry, Technische Universität Müchen, Garching, Germany. s.inoue@tum.de.ORCID http://orcid.org/0000-0001-6685-6352

Funding

EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council) ALLOWE101001591
6 · The paper itself

Abstract

Nitriles (R-C≡N) have been investigated since the late eighteenth century and are ubiquitous encounters in organic and inorganic syntheses. In contrast, heavier nitriles, which contain the heavier analogues of carbon and nitrogen, are sparsely investigated species. Here we report the synthesis and isolation of a phosphino-silylene featuring an N-heterocyclic carbene-phosphinidene and a highly sterically demanding silyl group as substituents. Due to its unique structural motif, it can be regarded as a Lewis base-stabilized heavier nitrile. The Si-P bond displays multiple bond character and a bent R-Si-P geometry, the latter indicating fundamental differences between heavier and classical nitriles. In solution, a quantitative unusual rearrangement to a phosphasilenylidene occurs. This rearrangement is consistent with theoretical predictions of rearrangements from heavier nitriles to heavier isonitriles. Our preliminary reactivity studies revealed that both isomers exhibit highly nucleophilic silicon centres capable of oxidative addition and coordination to iron tetracarbonyl.

Identifiers

PMID39256544
PMCPMC11611736

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.