C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the Click Chemistry.

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F16%3A00461198" target="_blank" >RIV/67985858:_____/16:00461198 - 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>

Jazyk výsledku

angličtina

Název v původním jazyce

C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the 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 (LCN) has been prepared and structurally characterized. Triorganotin(iv) azides of the type LCNR2SnN3 (R = n-Bu (1) and Ph (2)) and (LCN)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 LCNRSn(N3)2 (R = n-Bu and Ph) are monomeric with trigonal bipyramidal geometry around the tin atom as well. Finally, (LCN)2Sn(N3)2 contains a six-coordinated tin atom with heavily distorted octahedral geometry due to the presence of two LCN 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. κ-N1: LCN(n-Bu)2Sn(5-MeCN4), LCNPh2Sn(5-MeCN4), LCN(n-Bu)2Sn(5-Me2NCH2CN4), LCNPh2Sn(5-Me2NCH2CN4); and κ-N2: LCN(n-Bu)2Sn(5-t-BuCN4), LCNPh2Sn(5-t-BuCN4), LCN(n-Bu)2Sn(5-PhCN4), LCNPh2Sn(5-PhCN4)). Similarly, the reaction of 1 and 2 with cyclooctyne provided corresponding C,N-chelated di-n-butyl/diphenyltin(iv) κ-N1 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 the 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 (LCN) has been prepared and structurally characterized. Triorganotin(iv) azides of the type LCNR2SnN3 (R = n-Bu (1) and Ph (2)) and (LCN)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 LCNRSn(N3)2 (R = n-Bu and Ph) are monomeric with trigonal bipyramidal geometry around the tin atom as well. Finally, (LCN)2Sn(N3)2 contains a six-coordinated tin atom with heavily distorted octahedral geometry due to the presence of two LCN 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. κ-N1: LCN(n-Bu)2Sn(5-MeCN4), LCNPh2Sn(5-MeCN4), LCN(n-Bu)2Sn(5-Me2NCH2CN4), LCNPh2Sn(5-Me2NCH2CN4); and κ-N2: LCN(n-Bu)2Sn(5-t-BuCN4), LCNPh2Sn(5-t-BuCN4), LCN(n-Bu)2Sn(5-PhCN4), LCNPh2Sn(5-PhCN4)). Similarly, the reaction of 1 and 2 with cyclooctyne provided corresponding C,N-chelated di-n-butyl/diphenyltin(iv) κ-N1 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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

—

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

2-s2.0-84978036115