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 journalArticle

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
Externally publishedYes

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2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Hydrogen Bonding
Conformations
Hydrogen bonds
Coordination Complexes
Metal ions
Crystal structure
Nuclear magnetic resonance
Ions
Oxygen
Atoms
Carbon-13 Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides. / No, Kwanghyun; Lee, Jeong Hyeon; Yang, Seung Hwan; Yu, Sang Hyeok; Cho, Moon Hwan; Kim, Moon Jib; Kim, Jong Seung.

In: Journal of Organic Chemistry, Vol. 67, No. 9, 03.05.2002, p. 3165-3168.

Research output: Contribution to journalArticle

No, Kwanghyun ; Lee, Jeong Hyeon ; Yang, Seung Hwan ; Yu, Sang Hyeok ; Cho, Moon Hwan ; Kim, Moon Jib ; Kim, Jong Seung. / Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 9. pp. 3165-3168.
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AU - Yu, Sang Hyeok

AU - Cho, Moon Hwan

AU - Kim, Moon Jib

AU - Kim, Jong Seung

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