C,N-Chelated organotin(IV) azides: synthesis, structure and use within click chemistry.
Identifikátory výsledku
Kód výsledku v 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>
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
C,N-Chelated organotin(IV) azides: synthesis, structure and use within click chemistry.
Popis výsledku v původním jazyce
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.
Název v anglickém jazyce
C,N-Chelated organotin(IV) azides: synthesis, structure and use within click chemistry.
Popis výsledku anglicky
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.
Klasifikace
Druh
J<sub>x</sub> - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)
CEP obor
CA - Anorganická chemie
OECD FORD obor
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Návaznosti výsledku
Projekt
<a href="/cs/project/GAP207%2F12%2F0223" target="_blank" >GAP207/12/0223: Hybridní ligandy pro stabilizaci/specifickou aktivaci kovových center v nízkých oxidačních stavech.</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2016
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
New Journal of Chemistry
ISSN
1144-0546
e-ISSN
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Svazek periodika
40
Číslo periodika v rámci svazku
7
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
10
Strana od-do
5808-5817
Kód UT WoS článku
000385869600023
EID výsledku v databázi Scopus
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