Archives for Chemistry Experiments of Dibenzo-18-crown-6

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In contrast to 18-crown-6, the substituted crown ethers Benzo-18-crown-6, Dibenzo-18-crown-6, and Naphtho-18-crown-6 form in solution complexes with p-CH3-C6H4-N2(+)BF4(-) characterized by broad charge transfer absorption up to 550 nm.The formation constants lg Kc are 2,32 2,16 and 1,44 for Benzo-, Dibenzo-, and Naphtho-18-crown-6, respectively.Formation enthalpy DeltaH = -7,5 kJ/mol and entropy DeltaS = +18 J/K mol are measured in the case of p-Cl-C6H4-N2(+)BF4(-) and Dibenzo-18-crown-6 (20 deg C).Kc depends on substituents in the arene ring of the diazonium salts; rho = +0,8.Thermal dediazoniation in the presence of Crown ethers results in high yields of the corresponding arene.This is explained by a fast radical chain reaction between the diazonium salt and the polyether (Meerwein-Reduction).

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare