Abstract
A series of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides with four p-phenyl groups on their upper rim were synthesized. From the 1H and 13C 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.
Original language | English |
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Pages (from-to) | 3165-3168 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 67 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2002 May 3 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry