Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides
- Authors
- No, K; Lee, JH; Yang, SH; Yu, SH; Cho, MH; Kim, MJ; Kim, JS
- Issue Date
- May-2002
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.67, no.9, pp 3165 - 3168
- Pages
- 4
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 67
- Number
- 9
- Start Page
- 3165
- End Page
- 3168
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16415
- DOI
- 10.1021/jo011138i
- ISSN
- 0022-3263
1520-6904
- Abstract
- A series of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides with four p-phenyl groups on their upper rim were synthesized. From the H-1 and C-13 NMR and crystal structure, N-butylamido homooxacalix[4]arene (4) was found to be in the 1,3-alternate conformation and has intramolecular hydrogen bonding between N-H and facing oxygen atoms of the carbonyl O=C group. This hydrogen bonding decreased the metal ion complex ability. Transformation of the 1,3-alternate N-butylamido (4) into N-butylthioamido homooxacalix[4]arene (5) using Lawesson's reagent gave a conformational change to the C-1,2-alternate.
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