Synthesis and lithium ion selectivity of 14-crown-4 derivatives having bulky subunits

cis and trans isomers of 2-phenylcyclohexano-14-crown-4, 2,3-diphenylcyclohexano-14-crown-4 and 2,3-di-(1-adamantyl)-14-crown-4

Yoshito Tobe, Yuko Tsuchiya, Hidekazu Iketani, Koichiro Naemura, Kazuya Kobiro, Mayumi Kaji, Sachiko Tsuzuki, Koji Suzuki

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

cis- and trans-2-Phenylcyclohexano-14-crown-4, cis- and trans-2,3-diphenylcyclohexano-14-crown-4, and cis- and trans-2,3-di-(1-adamantyl)-14-crown-4 have been prepared and their ion selectivities toward alkali metal cations examined by means of the extraction of alkali metal picrates, the measurement of stability constants of the complexes with lithium or sodium perchlorate, and the electrode response potential measurement for the ion-sensitive membranes. The remarkable dependence of the complexation ability to Li+ on the cisltrans stereochemistry of the ionophores is discussed on the basis of their geometries estimated by molecular mechanics calculations and the structures of cis- and trans-diphenylcyclohexano derivatives determined by X-ray structure analyses. In order to assist the discussion, the X-ray structure analyses of the lithium picrate complex of decalino-14-crown-4 and the 2:1 'sandwich-type' complex of benzo-14-crown-4 with sodium perchlorate have also been undertaken.

Original languageEnglish
Pages (from-to)485-494
Number of pages10
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number3
Publication statusPublished - 1998 Feb 7

Fingerprint

Alkali Metals
Lithium
Isomers
Picrates
Ions
Derivatives
X rays
Stereochemistry
Molecular mechanics
Ionophores
Complexation
Cations
Membranes
Electrodes
Geometry
sodium perchlorate
picric acid
lithium perchlorate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and lithium ion selectivity of 14-crown-4 derivatives having bulky subunits : cis and trans isomers of 2-phenylcyclohexano-14-crown-4, 2,3-diphenylcyclohexano-14-crown-4 and 2,3-di-(1-adamantyl)-14-crown-4. / Tobe, Yoshito; Tsuchiya, Yuko; Iketani, Hidekazu; Naemura, Koichiro; Kobiro, Kazuya; Kaji, Mayumi; Tsuzuki, Sachiko; Suzuki, Koji.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 3, 07.02.1998, p. 485-494.

Research output: Contribution to journalArticle

@article{6b6e1da8abf34b138e35bed0c24e7495,
title = "Synthesis and lithium ion selectivity of 14-crown-4 derivatives having bulky subunits: cis and trans isomers of 2-phenylcyclohexano-14-crown-4, 2,3-diphenylcyclohexano-14-crown-4 and 2,3-di-(1-adamantyl)-14-crown-4",
abstract = "cis- and trans-2-Phenylcyclohexano-14-crown-4, cis- and trans-2,3-diphenylcyclohexano-14-crown-4, and cis- and trans-2,3-di-(1-adamantyl)-14-crown-4 have been prepared and their ion selectivities toward alkali metal cations examined by means of the extraction of alkali metal picrates, the measurement of stability constants of the complexes with lithium or sodium perchlorate, and the electrode response potential measurement for the ion-sensitive membranes. The remarkable dependence of the complexation ability to Li+ on the cisltrans stereochemistry of the ionophores is discussed on the basis of their geometries estimated by molecular mechanics calculations and the structures of cis- and trans-diphenylcyclohexano derivatives determined by X-ray structure analyses. In order to assist the discussion, the X-ray structure analyses of the lithium picrate complex of decalino-14-crown-4 and the 2:1 'sandwich-type' complex of benzo-14-crown-4 with sodium perchlorate have also been undertaken.",
author = "Yoshito Tobe and Yuko Tsuchiya and Hidekazu Iketani and Koichiro Naemura and Kazuya Kobiro and Mayumi Kaji and Sachiko Tsuzuki and Koji Suzuki",
year = "1998",
month = "2",
day = "7",
language = "English",
pages = "485--494",
journal = "Journal of the Chemical Society. Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
number = "3",

}

TY - JOUR

T1 - Synthesis and lithium ion selectivity of 14-crown-4 derivatives having bulky subunits

T2 - cis and trans isomers of 2-phenylcyclohexano-14-crown-4, 2,3-diphenylcyclohexano-14-crown-4 and 2,3-di-(1-adamantyl)-14-crown-4

AU - Tobe, Yoshito

AU - Tsuchiya, Yuko

AU - Iketani, Hidekazu

AU - Naemura, Koichiro

AU - Kobiro, Kazuya

AU - Kaji, Mayumi

AU - Tsuzuki, Sachiko

AU - Suzuki, Koji

PY - 1998/2/7

Y1 - 1998/2/7

N2 - cis- and trans-2-Phenylcyclohexano-14-crown-4, cis- and trans-2,3-diphenylcyclohexano-14-crown-4, and cis- and trans-2,3-di-(1-adamantyl)-14-crown-4 have been prepared and their ion selectivities toward alkali metal cations examined by means of the extraction of alkali metal picrates, the measurement of stability constants of the complexes with lithium or sodium perchlorate, and the electrode response potential measurement for the ion-sensitive membranes. The remarkable dependence of the complexation ability to Li+ on the cisltrans stereochemistry of the ionophores is discussed on the basis of their geometries estimated by molecular mechanics calculations and the structures of cis- and trans-diphenylcyclohexano derivatives determined by X-ray structure analyses. In order to assist the discussion, the X-ray structure analyses of the lithium picrate complex of decalino-14-crown-4 and the 2:1 'sandwich-type' complex of benzo-14-crown-4 with sodium perchlorate have also been undertaken.

AB - cis- and trans-2-Phenylcyclohexano-14-crown-4, cis- and trans-2,3-diphenylcyclohexano-14-crown-4, and cis- and trans-2,3-di-(1-adamantyl)-14-crown-4 have been prepared and their ion selectivities toward alkali metal cations examined by means of the extraction of alkali metal picrates, the measurement of stability constants of the complexes with lithium or sodium perchlorate, and the electrode response potential measurement for the ion-sensitive membranes. The remarkable dependence of the complexation ability to Li+ on the cisltrans stereochemistry of the ionophores is discussed on the basis of their geometries estimated by molecular mechanics calculations and the structures of cis- and trans-diphenylcyclohexano derivatives determined by X-ray structure analyses. In order to assist the discussion, the X-ray structure analyses of the lithium picrate complex of decalino-14-crown-4 and the 2:1 'sandwich-type' complex of benzo-14-crown-4 with sodium perchlorate have also been undertaken.

UR - http://www.scopus.com/inward/record.url?scp=33748648890&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748648890&partnerID=8YFLogxK

M3 - Article

SP - 485

EP - 494

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

SN - 1472-7781

IS - 3

ER -