Interaction of Sulfonamides with Cyclic Polyether 18-Crown-6 in Solution and in Solid State

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The interaction of sulfonamides with 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane) was studied, observing the effect on the solubility of sulfonamides in organic solvents. In benzene solution, sulfamonomethoxine and sulfamethoxazole formed the respective crystalline complexes with 18-crown-6. The stability constant K for sulfamonomethoxine/18-crown-6 system was particularly large in comparison with the other systems. In chloroform solution, however, the solid complex was not obtained in any systems. K values in chloroform were smaller than those in benzene. Furthermore, when the complex formation of sulfamethomidine with 18-crown-6 was investigated in various dielectric constants of solvents, K value decreased with the increase in polarity of the solvent. These results indicated that the hydrogen bonding might be a primary force of the formation of these complexes. Additionally, the complex formation in solid phase was confirmed in sulfamonomethoxine/18-crown-6 and sulfamethoxazole/18-crown-6 systems by powder X-ray diffractometry and differential scanning calorimetry. From infra-red and nuclear magnetic resonance spectra, it was suggested that 4-amino group of sulfonamide might interact with the oxygen of ether ring of 18-crown-6.
1977-10-25