Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides

Kwanghyun No, Jeong Hyeon Lee, Seung Hwan Yang, Sang Hyeok Yu, Moon Hwan Cho, Moon Jib Kim, Jong Seung Kim

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

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 languageEnglish
Pages (from-to)3165-3168
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number9
DOIs
Publication statusPublished - 2002 May 3

ASJC Scopus subject areas

  • Organic Chemistry

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