Synthesis, characterization and conformational study of new α,β-unsaturated acylhydrazones based on calix [4]arene backbone
| Autor: | Marwa Fray, Thouraya Barhoumi-Slimi, Rym Abidi, Imane Hamzi |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Nuclear magnetic resonance spectroscopy 010402 general chemistry Hydrazide 01 natural sciences Nmr data 0104 chemical sciences Analytical Chemistry Characterization (materials science) Inorganic Chemistry Crystallography chemistry.chemical_compound chemistry Conformational isomerism Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1185:78-84 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2019.02.047 |
| Popis: | A series of six new p-tert-butylcalix [4]arene-1,3-N,N′-diacylhydrazone derivatives 1–6 have been synthesized starting from β-chloro-α,β-unsaturated aldehydes and p-tert-butylcalix [4]arene hydrazide. They were characterized by IR, (1H, 13C, 19F) NMR and HRMS. In addition of the E/Z isomers around the C C bond of the starting aldehydes, the NMR data showed three conformers due to N C(O) bond rotation: transamid/transamid; Cisamid/transamid and Cisamid/Cisamid resulting from the disubstitution of calix [4]arenes. The rotational barriers around N C(O) bond for most compounds were measured in dimethylsulfoxide using dynamic NMR spectroscopy (DNMR). The results are discussed and compared with those previously reported for related β-chloro-α,β-unsaturated acylhydrazones. |
| Databáze: | OpenAIRE |
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