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Direct Observation of Carbamoylnitrenes.

Identifieur interne : 001D26 ( PubMed/Corpus ); précédent : 001D25; suivant : 001D27

Direct Observation of Carbamoylnitrenes.

Auteurs : Hongmin Li ; Huabin Wan ; Zhuang Wu ; Dingqing Li ; Didier Bégué ; Curt Wentrup ; Xiaoqing Zeng

Source :

Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.

RBID : pubmed:27105905

Abstract

As the prototype Curtius rearrangement reaction, carbamoyl azide decomposes into aminoisocyanate and molecular nitrogen. However, the key intermediate carbamoylnitrene was previously undetected, even though the decomposition of carbamoyl azides has been studied frequently since its discovery in the 1890s. Upon ArF laser (λ=193 nm) photolysis, the stepwise decomposition of the two simplest carbamoyl azides H2 NC(O)N3 and Me2 NC(O)N3, isolated in solid noble gas matrices, occurs with the formation of the corresponding carbamoylnitrenes H2 NC(O)N and Me2 NC(O)N. Both triplet species are characterized for the first time by combining matrix-isolation IR spectroscopy and quantum-chemical calculations. Subsequent visible-light irradiations cause efficient rearrangement of these nitrenes into the respective aminoisocyanates.

DOI: 10.1002/chem.201600824
PubMed: 27105905

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Le document en format XML

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<author><name sortKey="Li, Hongmin" sort="Li, Hongmin" uniqKey="Li H" first="Hongmin" last="Li">Hongmin Li</name>
<affiliation><nlm:affiliation>The Key Lab of Health Chemistry and Molecular Diagnosis of Suzhou, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P.R. China.</nlm:affiliation>
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<author><name sortKey="Wan, Huabin" sort="Wan, Huabin" uniqKey="Wan H" first="Huabin" last="Wan">Huabin Wan</name>
<affiliation><nlm:affiliation>The Key Lab of Health Chemistry and Molecular Diagnosis of Suzhou, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P.R. China.</nlm:affiliation>
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<author><name sortKey="Wu, Zhuang" sort="Wu, Zhuang" uniqKey="Wu Z" first="Zhuang" last="Wu">Zhuang Wu</name>
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<author><name sortKey="Li, Dingqing" sort="Li, Dingqing" uniqKey="Li D" first="Dingqing" last="Li">Dingqing Li</name>
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<author><name sortKey="Begue, Didier" sort="Begue, Didier" uniqKey="Begue D" first="Didier" last="Bégué">Didier Bégué</name>
<affiliation><nlm:affiliation>Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux (IPREM), Université de Pau et des Pays de l'Adour, 64000, Pau, France.</nlm:affiliation>
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<author><name sortKey="Wentrup, Curt" sort="Wentrup, Curt" uniqKey="Wentrup C" first="Curt" last="Wentrup">Curt Wentrup</name>
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<author><name sortKey="Zeng, Xiaoqing" sort="Zeng, Xiaoqing" uniqKey="Zeng X" first="Xiaoqing" last="Zeng">Xiaoqing Zeng</name>
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<author><name sortKey="Wu, Zhuang" sort="Wu, Zhuang" uniqKey="Wu Z" first="Zhuang" last="Wu">Zhuang Wu</name>
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<author><name sortKey="Begue, Didier" sort="Begue, Didier" uniqKey="Begue D" first="Didier" last="Bégué">Didier Bégué</name>
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<author><name sortKey="Wentrup, Curt" sort="Wentrup, Curt" uniqKey="Wentrup C" first="Curt" last="Wentrup">Curt Wentrup</name>
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<author><name sortKey="Zeng, Xiaoqing" sort="Zeng, Xiaoqing" uniqKey="Zeng X" first="Xiaoqing" last="Zeng">Xiaoqing Zeng</name>
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<front><div type="abstract" xml:lang="en">As the prototype Curtius rearrangement reaction, carbamoyl azide decomposes into aminoisocyanate and molecular nitrogen. However, the key intermediate carbamoylnitrene was previously undetected, even though the decomposition of carbamoyl azides has been studied frequently since its discovery in the 1890s. Upon ArF laser (λ=193 nm) photolysis, the stepwise decomposition of the two simplest carbamoyl azides H2 NC(O)N3 and Me2 NC(O)N3, isolated in solid noble gas matrices, occurs with the formation of the corresponding carbamoylnitrenes H2 NC(O)N and Me2 NC(O)N. Both triplet species are characterized for the first time by combining matrix-isolation IR spectroscopy and quantum-chemical calculations. Subsequent visible-light irradiations cause efficient rearrangement of these nitrenes into the respective aminoisocyanates.</div>
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<Abstract><AbstractText>As the prototype Curtius rearrangement reaction, carbamoyl azide decomposes into aminoisocyanate and molecular nitrogen. However, the key intermediate carbamoylnitrene was previously undetected, even though the decomposition of carbamoyl azides has been studied frequently since its discovery in the 1890s. Upon ArF laser (λ=193 nm) photolysis, the stepwise decomposition of the two simplest carbamoyl azides H2 NC(O)N3 and Me2 NC(O)N3, isolated in solid noble gas matrices, occurs with the formation of the corresponding carbamoylnitrenes H2 NC(O)N and Me2 NC(O)N. Both triplet species are characterized for the first time by combining matrix-isolation IR spectroscopy and quantum-chemical calculations. Subsequent visible-light irradiations cause efficient rearrangement of these nitrenes into the respective aminoisocyanates.</AbstractText>
<CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation>
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<Keyword MajorTopicYN="Y">IR spectroscopy</Keyword>
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Direct Observation of Carbamoylnitrenes.

Direct Observation of Carbamoylnitrenes.

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