Enhanced acidity and facile complexation of amines with a phenol trimer

Naoto Hayashi; Hiroyuki Higuchi; Hiroaki Miyazawa; Kiyoshi Matsumoto

doi:10.1080/15421400590957729

Enhanced acidity and facile complexation of amines with a phenol trimer

Naoto Hayashi^*, Hiroyuki Higuchi, Hiroaki Miyazawa, Kiyoshi Matsumoto

^*Corresponding author for this work

Department of Chemistry

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

Abstract

The phenol trimer, 5,5′,5″-trichloro-1,17prime;:3′, 1′-terphenyl-2,2′,2″-triol (1), facilely affords the 1:1 complex (I) with triethylamine owing to its enhanced acidity. IR spectra reveal that I is a proton transfer complex. In the X-ray structure of I, a long phenoxide C-O bond is observed that may be due to unusual sp³ hybridization of the phenoxide oxygen atom caused by strong intra- and inter-molecular hydrogen bonding.

Original language	English
Pages (from-to)	65-69
Number of pages	5
Journal	Molecular Crystals and Liquid Crystals
Volume	440
DOIs	https://doi.org/10.1080/15421400590957729
State	Published - 2005

Keywords

Amine complex
Bond length
Phenoxide
Proton transfer complex
X-ray structure

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1080/15421400590957729

Cite this

@article{49fd38af4e63428e989f1f65cedef5c5,

title = "Enhanced acidity and facile complexation of amines with a phenol trimer",

abstract = "The phenol trimer, 5,5′,5″-trichloro-1,17prime;:3′, 1′-terphenyl-2,2′,2″-triol (1), facilely affords the 1:1 complex (I) with triethylamine owing to its enhanced acidity. IR spectra reveal that I is a proton transfer complex. In the X-ray structure of I, a long phenoxide C-O bond is observed that may be due to unusual sp3 hybridization of the phenoxide oxygen atom caused by strong intra- and inter-molecular hydrogen bonding.",

keywords = "Amine complex, Bond length, Phenoxide, Proton transfer complex, X-ray structure",

author = "Naoto Hayashi and Hiroyuki Higuchi and Hiroaki Miyazawa and Kiyoshi Matsumoto",

note = "Funding Information: Keywords: amine complex; bond length; phenoxide; proton transfer complex; X-ray structure Financial support of this work by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan (90281104) is gratefully acknowledged. The authors are also grateful to the Ministry of Education, Culture, Sports, Science, and Technology, Japan for purchasing the high-field NMR instruments (JEOL JNM-A500 and JNM-EX270) by the special fund to K. M. in 1992.",

year = "2005",

doi = "10.1080/15421400590957729",

language = "英語",

volume = "440",

pages = "65--69",

journal = "Molecular Crystals and Liquid Crystals",

issn = "1542-1406",

publisher = "Taylor and Francis Ltd.",

}

TY - JOUR

T1 - Enhanced acidity and facile complexation of amines with a phenol trimer

AU - Hayashi, Naoto

AU - Higuchi, Hiroyuki

AU - Miyazawa, Hiroaki

AU - Matsumoto, Kiyoshi

N1 - Funding Information: Keywords: amine complex; bond length; phenoxide; proton transfer complex; X-ray structure Financial support of this work by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan (90281104) is gratefully acknowledged. The authors are also grateful to the Ministry of Education, Culture, Sports, Science, and Technology, Japan for purchasing the high-field NMR instruments (JEOL JNM-A500 and JNM-EX270) by the special fund to K. M. in 1992.

PY - 2005

Y1 - 2005

N2 - The phenol trimer, 5,5′,5″-trichloro-1,17prime;:3′, 1′-terphenyl-2,2′,2″-triol (1), facilely affords the 1:1 complex (I) with triethylamine owing to its enhanced acidity. IR spectra reveal that I is a proton transfer complex. In the X-ray structure of I, a long phenoxide C-O bond is observed that may be due to unusual sp3 hybridization of the phenoxide oxygen atom caused by strong intra- and inter-molecular hydrogen bonding.

AB - The phenol trimer, 5,5′,5″-trichloro-1,17prime;:3′, 1′-terphenyl-2,2′,2″-triol (1), facilely affords the 1:1 complex (I) with triethylamine owing to its enhanced acidity. IR spectra reveal that I is a proton transfer complex. In the X-ray structure of I, a long phenoxide C-O bond is observed that may be due to unusual sp3 hybridization of the phenoxide oxygen atom caused by strong intra- and inter-molecular hydrogen bonding.

KW - Amine complex

KW - Bond length

KW - Phenoxide

KW - Proton transfer complex

KW - X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=33644783740&partnerID=8YFLogxK

U2 - 10.1080/15421400590957729

DO - 10.1080/15421400590957729

M3 - 学術論文

AN - SCOPUS:33644783740

SN - 1542-1406

VL - 440

SP - 65

EP - 69

JO - Molecular Crystals and Liquid Crystals

JF - Molecular Crystals and Liquid Crystals

ER -

Enhanced acidity and facile complexation of amines with a phenol trimer

Abstract

Keywords

ASJC Scopus subject areas

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