High-resolution solid-state carbon-13 NMR study of free and metal-complexed macrocyclic antibiotic ionophores valinomycin, nonactin, and tetranctin: conformational elucidation in solid and solution by conformation-dependent carbon-13 chemical shifts

Biochemistry ◽  
1985 ◽  
Vol 24 (26) ◽  
pp. 7696-7702 ◽  
Author(s):  
Ryoko Tabeta ◽  
Hazime Saito
2005 ◽  
Vol 61 (1) ◽  
pp. 88-94 ◽  
Author(s):  
S CADARS ◽  
M FORAY ◽  
A GADELLE ◽  
G GERBAUD ◽  
M BARDET

2001 ◽  
Vol 79 (2) ◽  
pp. 195-200 ◽  
Author(s):  
Gerald W Buchanan ◽  
Majid F Rastegar ◽  
Glenn PA Yap

Benzo-9-crown-3 ether trimerizes in the presence of FeCl3 and aqueous H2SO4 to produce tris(9-crown-3)triphenylene in 25.4% yield. This compound crystallizes in the monoclinic P21/c space group: a = 13.759(2) Å, b = 13.318(2) Å, c = 13.399(2) Å, β = 96.883(2)°, with Z = 4. The three 9-crown-3 ether units of the trimer possess different geometries and there is substantial deviation from coplanarity in the three aromatic rings. 13C NMR chemical shifts in the solid state are consistent with this lack of symmetry and are discussed in terms of the X-ray crystal-structure data.Key words: crown ether, trimerization, stereochemistry.


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