Synthesis, NMR and DFT conformational studies of homooxacalixarene (cyanopropyl)oxy derivatives, precursors to urea-terminated compounds
Tetrahedron(2013)
Abstract
Direct O-alkylation of the parent compounds p-tert-butyldihomooxacalix[4]arene (1) and p-tert-butylhexahomotrioxacalix[3]arene (3) with 4-bromobutyronitrile and K2CO3 in acetonitrile afforded tetra- and tri-[(cyanopropyl)oxy] derivatives 2 and 4, respectively, as a mixture of conformers. These conformers were isolated and their conformational features studied by NMR spectroscopy (1H, 13C, COSY and NOESY) and DFT methods. Dihomooxacalix[4]arene tetra[(cyanobutyl)oxy] derivative 5 was also obtained and studied for comparison purposes. In general, good agreement was obtained between theoretical calculations and the NMR experimental data. For compounds 2 and 4 the partial cone conformation was the most stable, while the cone conformation was the most stable for derivative 5.
MoreTranslated text
Key words
Homooxacalixarenes,Synthesis,Cyano derivatives,Conformational analysis,NMR spectroscopy,DFT methods
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined