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

doi:10.1021/jo011138i

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 journal › Article › peer-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 language	English
Pages (from-to)	3165-3168
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	67
Issue number	9
DOIs	https://doi.org/10.1021/jo011138i
Publication status	Published - 2002 May 3
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo011138i

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title = "Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides",

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.",

author = "Kwanghyun No and Lee, {Jeong Hyeon} and Yang, {Seung Hwan} and Yu, {Sang Hyeok} and Cho, {Moon Hwan} and Kim, {Moon Jib} and Kim, {Jong Seung}",

year = "2002",

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volume = "67",

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publisher = "American Chemical Society",

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T1 - Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides

AU - No, Kwanghyun

AU - Lee, Jeong Hyeon

AU - Yang, Seung Hwan

AU - Yu, Sang Hyeok

AU - Cho, Moon Hwan

AU - Kim, Moon Jib

AU - Kim, Jong Seung

PY - 2002/5/3

Y1 - 2002/5/3

N2 - 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.

AB - 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.

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

Abstract

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