Unusual hydrogen-bonding networks consisting of π-extended 4,4′-bipyridines and chloranilic acid

Md Akhtaruzzaman; Masaaki Tomura; Kazuko Takahashi; Jun Ichi Nishida; Yoshiro Yamashita

doi:10.1080/1061027031000080533

Unusual hydrogen-bonding networks consisting of π-extended 4,4′-bipyridines and chloranilic acid

Md Akhtaruzzaman, Masaaki Tomura, Kazuko Takahashi, Jun Ichi Nishida, Yoshiro Yamashita

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

5 Citations (Scopus)

Abstract

Hydrogen-bonding networks of π-extended 4,4′-bipyridines, 2,5-di(4-pyridyl)thiophene (1), 2,5-di(4-pyridyl)-furan (2) and 1,4-di(4-pyridyl)benzene (3) with 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid, CA) have been investigated. The dipyridyl compounds afforded complexes 4 [(dication of 1)·(monoanion of CA)₂], 5 [(dication of 2)·(dianion of CA)·(MeOH)] and 6 [(3)·(dication of 3)·(dianion of CA)·(H₂O)₆] with CA. X-ray structure analyses revealed the formation of unusual molecular tape and sheet structures involving N-H⋯O, O-H⋯O, C-H⋯O and N-H⋯N hydrogen bonds, where the aromatic spacer groups play an important role in constructing the unique crystal structures.

Original language	English
Pages (from-to)	239-243
Number of pages	5
Journal	Supramolecular Chemistry
Volume	15
Issue number	4
DOIs	https://doi.org/10.1080/1061027031000080533
Publication status	Published - 2003 Jun
Externally published	Yes

Keywords

Chloranilic acid
Crystal engineering
Hydrogen-bonding network
π-Extended bipyridines

ASJC Scopus subject areas

Chemistry(all)

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10.1080/1061027031000080533

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title = "Unusual hydrogen-bonding networks consisting of π-extended 4,4′-bipyridines and chloranilic acid",

abstract = "Hydrogen-bonding networks of π-extended 4,4′-bipyridines, 2,5-di(4-pyridyl)thiophene (1), 2,5-di(4-pyridyl)-furan (2) and 1,4-di(4-pyridyl)benzene (3) with 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid, CA) have been investigated. The dipyridyl compounds afforded complexes 4 [(dication of 1)·(monoanion of CA)2], 5 [(dication of 2)·(dianion of CA)·(MeOH)] and 6 [(3)·(dication of 3)·(dianion of CA)·(H2O)6] with CA. X-ray structure analyses revealed the formation of unusual molecular tape and sheet structures involving N-H⋯O, O-H⋯O, C-H⋯O and N-H⋯N hydrogen bonds, where the aromatic spacer groups play an important role in constructing the unique crystal structures.",

keywords = "Chloranilic acid, Crystal engineering, Hydrogen-bonding network, π-Extended bipyridines",

author = "Md Akhtaruzzaman and Masaaki Tomura and Kazuko Takahashi and Nishida, {Jun Ichi} and Yoshiro Yamashita",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2003",

month = jun,

doi = "10.1080/1061027031000080533",

language = "English",

volume = "15",

pages = "239--243",

journal = "Supramolecular Chemistry",

issn = "1061-0278",

publisher = "Taylor and Francis Ltd.",

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TY - JOUR

T1 - Unusual hydrogen-bonding networks consisting of π-extended 4,4′-bipyridines and chloranilic acid

AU - Akhtaruzzaman, Md

AU - Tomura, Masaaki

AU - Takahashi, Kazuko

AU - Nishida, Jun Ichi

AU - Yamashita, Yoshiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2003/6

Y1 - 2003/6

N2 - Hydrogen-bonding networks of π-extended 4,4′-bipyridines, 2,5-di(4-pyridyl)thiophene (1), 2,5-di(4-pyridyl)-furan (2) and 1,4-di(4-pyridyl)benzene (3) with 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid, CA) have been investigated. The dipyridyl compounds afforded complexes 4 [(dication of 1)·(monoanion of CA)2], 5 [(dication of 2)·(dianion of CA)·(MeOH)] and 6 [(3)·(dication of 3)·(dianion of CA)·(H2O)6] with CA. X-ray structure analyses revealed the formation of unusual molecular tape and sheet structures involving N-H⋯O, O-H⋯O, C-H⋯O and N-H⋯N hydrogen bonds, where the aromatic spacer groups play an important role in constructing the unique crystal structures.

AB - Hydrogen-bonding networks of π-extended 4,4′-bipyridines, 2,5-di(4-pyridyl)thiophene (1), 2,5-di(4-pyridyl)-furan (2) and 1,4-di(4-pyridyl)benzene (3) with 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid, CA) have been investigated. The dipyridyl compounds afforded complexes 4 [(dication of 1)·(monoanion of CA)2], 5 [(dication of 2)·(dianion of CA)·(MeOH)] and 6 [(3)·(dication of 3)·(dianion of CA)·(H2O)6] with CA. X-ray structure analyses revealed the formation of unusual molecular tape and sheet structures involving N-H⋯O, O-H⋯O, C-H⋯O and N-H⋯N hydrogen bonds, where the aromatic spacer groups play an important role in constructing the unique crystal structures.

KW - Chloranilic acid

KW - Crystal engineering

KW - Hydrogen-bonding network

KW - π-Extended bipyridines

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DO - 10.1080/1061027031000080533

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Unusual hydrogen-bonding networks consisting of π-extended 4,4′-bipyridines and chloranilic acid

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