Crystal structure and inclusion property of p-tert- butylthiacalix[6]arene

Nobuhiko Iki; Naoya Morohashi; Tomohiro Suzuki; Satoshi Ogawa; Mitsuru Aono; Chizuko Kabuto; Hitoshi Kumagai; Haruhiko Takeya; Setsuko Miyanari; Sotaro Miyano

doi:10.1016/S0040-4039(00)00211-2

Crystal structure and inclusion property of p-tert- butylthiacalix[6]arene

Nobuhiko Iki, Naoya Morohashi, Tomohiro Suzuki, Satoshi Ogawa, Mitsuru Aono, Chizuko Kabuto, Hitoshi Kumagai, Haruhiko Takeya, Setsuko Miyanari, Sotaro Miyano

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

Although the reaction of p-tert-butylphenol with elemental sulfur in the presence of CsOH as a base catalyst yielded a complex mixture comprised of sulfur-bridged phenol oligomers, p-tert-butylthiacalix[6]arene (TC6A) could be isolated in an appreciable yield (0.8%). The X-ray analysis revealed that TC6A adopted a distorted cone conformation stabilized by two sets of hydrogen bondings comprising three phenolic OH groups. The recrystallization from various solvents showed that TC6A had higher inclusion ability toward more guests than TC4A did, suggesting that the expanded central cavity and/or the crystal lattice of the former allowed a more comfortable accommodation of the guest molecules. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2587-2590
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(00)00211-2
Publication status	Published - 2000 Apr 8

Keywords

Calixarenes
Inclusion
Sulfurization
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)00211-2

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title = "Crystal structure and inclusion property of p-tert- butylthiacalix[6]arene",

abstract = "Although the reaction of p-tert-butylphenol with elemental sulfur in the presence of CsOH as a base catalyst yielded a complex mixture comprised of sulfur-bridged phenol oligomers, p-tert-butylthiacalix[6]arene (TC6A) could be isolated in an appreciable yield (0.8%). The X-ray analysis revealed that TC6A adopted a distorted cone conformation stabilized by two sets of hydrogen bondings comprising three phenolic OH groups. The recrystallization from various solvents showed that TC6A had higher inclusion ability toward more guests than TC4A did, suggesting that the expanded central cavity and/or the crystal lattice of the former allowed a more comfortable accommodation of the guest molecules. (C) 2000 Elsevier Science Ltd.",

keywords = "Calixarenes, Inclusion, Sulfurization, X-ray crystal structures",

author = "Nobuhiko Iki and Naoya Morohashi and Tomohiro Suzuki and Satoshi Ogawa and Mitsuru Aono and Chizuko Kabuto and Hitoshi Kumagai and Haruhiko Takeya and Setsuko Miyanari and Sotaro Miyano",

note = "Funding Information: This work was supported by the Proposal-Based New Industry Creative Type Technology R&D Promotion Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.",

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doi = "10.1016/S0040-4039(00)00211-2",

language = "English",

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T1 - Crystal structure and inclusion property of p-tert- butylthiacalix[6]arene

AU - Iki, Nobuhiko

AU - Morohashi, Naoya

AU - Suzuki, Tomohiro

AU - Ogawa, Satoshi

AU - Aono, Mitsuru

AU - Kabuto, Chizuko

AU - Kumagai, Hitoshi

AU - Takeya, Haruhiko

AU - Miyanari, Setsuko

AU - Miyano, Sotaro

N1 - Funding Information: This work was supported by the Proposal-Based New Industry Creative Type Technology R&D Promotion Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.

PY - 2000/4/8

Y1 - 2000/4/8

N2 - Although the reaction of p-tert-butylphenol with elemental sulfur in the presence of CsOH as a base catalyst yielded a complex mixture comprised of sulfur-bridged phenol oligomers, p-tert-butylthiacalix[6]arene (TC6A) could be isolated in an appreciable yield (0.8%). The X-ray analysis revealed that TC6A adopted a distorted cone conformation stabilized by two sets of hydrogen bondings comprising three phenolic OH groups. The recrystallization from various solvents showed that TC6A had higher inclusion ability toward more guests than TC4A did, suggesting that the expanded central cavity and/or the crystal lattice of the former allowed a more comfortable accommodation of the guest molecules. (C) 2000 Elsevier Science Ltd.

AB - Although the reaction of p-tert-butylphenol with elemental sulfur in the presence of CsOH as a base catalyst yielded a complex mixture comprised of sulfur-bridged phenol oligomers, p-tert-butylthiacalix[6]arene (TC6A) could be isolated in an appreciable yield (0.8%). The X-ray analysis revealed that TC6A adopted a distorted cone conformation stabilized by two sets of hydrogen bondings comprising three phenolic OH groups. The recrystallization from various solvents showed that TC6A had higher inclusion ability toward more guests than TC4A did, suggesting that the expanded central cavity and/or the crystal lattice of the former allowed a more comfortable accommodation of the guest molecules. (C) 2000 Elsevier Science Ltd.

KW - Calixarenes

KW - Inclusion

KW - Sulfurization

KW - X-ray crystal structures

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U2 - 10.1016/S0040-4039(00)00211-2

DO - 10.1016/S0040-4039(00)00211-2

M3 - Article

AN - SCOPUS:3042635014

SN - 0040-4039

VL - 41

SP - 2587

EP - 2590

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Crystal structure and inclusion property of p-tert- butylthiacalix[6]arene

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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