The conformation and dynamic behaviour of tetrathiacalix[4]arenes functionalized by hydrazide and hydrazone groups |
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Authors: | Victor V Syakaev Sergey N Podyachev Aidar T Gubaidullin Svetlana N Sudakova Alexander I Konovalov |
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Institution: | aA. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of Russian Academy of Sciences, Arbuzov Str., 8, 420088 Kazan, Russia |
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Abstract: | The 1H, 13C and 15N NMR data, conformation and dynamic behaviour of the new tetrathiacalix4]arenes functionalized by hydrazide and hydrazone groups are reported and compared with the result of earlier investigations of 4-tert-butylphenoxyacetylhydrazones. The unusual fact of formation of N,N′-diacetylhydrazine bridge and factors leading to its formation in the cone conformer of calixarene has been discussed. The barriers of rotation of hydrazone fragments of tetrathiacalix4]arenes were determined by NMR-measurements at various temperatures. The structure of 1,3-alternate conformer of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakishydrazinocarbonylmethyl]-2,8,14,20-tetrathiacalix4]arene in solution is compared with crystal structure obtained by the X-ray analysis. |
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Keywords: | Calix[4]arene Hydrazide Hydrazone NMR spectroscopy X-ray crystallography |
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