C,N-Chelated organotin(IV) azides: synthesis, structure and use within click chemistry.
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F16%3A39901654" target="_blank" >RIV/00216275:25310/16:39901654 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1039/c5nj03187g" target="_blank" >http://dx.doi.org/10.1039/c5nj03187g</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c5nj03187g" target="_blank" >10.1039/c5nj03187g</a>
Alternative languages
Result language
angličtina
Original language name
C,N-Chelated organotin(IV) azides: synthesis, structure and use within click chemistry.
Original language description
A set of tri-and diorganotin(IV) azides bearing 2-(N, N-dimethylaminomethyl)phenyl as a C,N-chelating ligand (L-CN) has been prepared and structurally characterized. Triorganotin(IV) azides of the type (LR2SnN3)-R-CN (R = n-Bu (1) and Ph (2)) and (L-CN)(2)(n-Bu)SnN3 are monomeric both in solution and in the solid state. The central tin atom in these species is five-coordinated with distorted trigonal bipyramidal geometry. Diorganotin(IV) azides of the type (LRSn)-R-CN(N-3)(2) (R = n-Bu and Ph) are monomeric with trigonal bipyramidal geometry around the tin atom as well. Finally, (L-CN)(2)Sn(N-3)(2) contains a six-coordinated tin atom with heavily distorted octahedral geometry due to the presence of two L-CN units. The potential use of selected organotin(IV) azides 1 and 2 as useful building blocks within click chemistry was investigated. The reactions of 1 and 2 with various nitriles resulted in the formation of corresponding triorganotin(IV) tetrazolides (i.e. kappa-N-1: L-CN(n-Bu)(2)Sn(5-MeCN4), (LPh2Sn)-Ph-CN(5-MeCN4), L-CN(n-Bu)(2)Sn(5-Me2NCH2CN4), (LPh2Sn)-Ph-CN(5-Me2NCH2CN4); and kappa-N-2: L-CN(n-Bu)(2)Sn(5-t-BuCN4), (LPh2Sn)-Ph-CN(5-t-BuCN4), L-CN(n-Bu)(2)Sn(5-PhCN4), (LPh2Sn)-Ph-CN(5-PhCN4)). Similarly, the reaction of 1 and 2 with cyclooctyne provided corresponding C, N-chelated di-n-butyl/diphenyltin(IV) kappa-N-1 4,5,6,7,8,9-hexahydrocycloocta[d][1,2,3] triazol-1-ides. All azido complexes and products of the [3+2] cycloaddition reactions were characterized by the combination of elemental analysis, mass spectrometry, IR spectroscopy, multinuclear NMR spectroscopy and, in the case of crystalline materials, XRD analysis. In addition, DFT calculations were carried out within the click chemistry reactions in order to corroborate the preferred formation of the respective tetrazolide regioisomer.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CA - Inorganic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GAP207%2F12%2F0223" target="_blank" >GAP207/12/0223: Hybrid ligands for low valent metal centres stabilization/specific activation.</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
New Journal of Chemistry
ISSN
1144-0546
e-ISSN
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Volume of the periodical
40
Issue of the periodical within the volume
7
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
5808-5817
UT code for WoS article
000385869600023
EID of the result in the Scopus database
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