Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

Peter R. Ashton; Richard A. Bartsch; Stuart J. Cantrill; Robert E. Hanes; Sarah K. Hickingbottom; James N. Lowe; Jon A. Preece; J. Fraser Stoddart; Vladimir S. Talanov; Zhen He Wang

doi:10.1016/S0040-4039(99)00553-5

Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

Peter R. Ashton, Richard A. Bartsch, Stuart J. Cantrill, Robert E. Hanes, Sarah K. Hickingbottom, James N. Lowe, Jon A. Preece, J. Fraser Stoddart^*, Vladimir S. Talanov, Zhen He Wang

^*Corresponding author for this work

Chemistry

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

59 Scopus citations

Abstract

A range of crown ethers with either [24]crown-8 or [25]crown-8 constitutions have been demonstrated to form pseudorotaxanes with para- disubstituted dibenzylammonium ions, both in solution and in the 'gas phase' by ¹H NMR spectroscopy and liquid secondary ion mass spectrometry, respectively. Substitution of the [24]crown-8 framework with increasing numbers of benzo rings is observed to lower the stability constants (K(a)'S) from >10³ to ~0 M^-1 in acetonitrile. A pronounced decrease in K(a) values also occurs when the [24]crown-8 constitution is expanded to give a macroring containing 25 atoms a modification that not only increases the size of the macrocyclic cavity but also disrupts the O-C-C-O repeating unit in the macrocycle's backbone.

Original language	English (US)
Pages (from-to)	3661-3664
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(99)00553-5
State	Published - May 7 1999

Keywords

Crown ethers
Pseudorotaxanes
Substituted ammonium ion binding
Supramolecular chemistry

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00553-5

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title = "Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles",

abstract = "A range of crown ethers with either [24]crown-8 or [25]crown-8 constitutions have been demonstrated to form pseudorotaxanes with para- disubstituted dibenzylammonium ions, both in solution and in the 'gas phase' by 1H NMR spectroscopy and liquid secondary ion mass spectrometry, respectively. Substitution of the [24]crown-8 framework with increasing numbers of benzo rings is observed to lower the stability constants (K(a)'S) from >103 to ~0 M-1 in acetonitrile. A pronounced decrease in K(a) values also occurs when the [24]crown-8 constitution is expanded to give a macroring containing 25 atoms a modification that not only increases the size of the macrocyclic cavity but also disrupts the O-C-C-O repeating unit in the macrocycle's backbone.",

keywords = "Crown ethers, Pseudorotaxanes, Substituted ammonium ion binding, Supramolecular chemistry",

author = "Ashton, {Peter R.} and Bartsch, {Richard A.} and Cantrill, {Stuart J.} and Hanes, {Robert E.} and Hickingbottom, {Sarah K.} and Lowe, {James N.} and Preece, {Jon A.} and Stoddart, {J. Fraser} and Talanov, {Vladimir S.} and Wang, {Zhen He}",

year = "1999",

month = may,

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doi = "10.1016/S0040-4039(99)00553-5",

language = "English (US)",

volume = "40",

pages = "3661--3664",

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T1 - Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

AU - Ashton, Peter R.

AU - Bartsch, Richard A.

AU - Cantrill, Stuart J.

AU - Hanes, Robert E.

AU - Hickingbottom, Sarah K.

AU - Lowe, James N.

AU - Preece, Jon A.

AU - Stoddart, J. Fraser

AU - Talanov, Vladimir S.

AU - Wang, Zhen He

PY - 1999/5/7

Y1 - 1999/5/7

N2 - A range of crown ethers with either [24]crown-8 or [25]crown-8 constitutions have been demonstrated to form pseudorotaxanes with para- disubstituted dibenzylammonium ions, both in solution and in the 'gas phase' by 1H NMR spectroscopy and liquid secondary ion mass spectrometry, respectively. Substitution of the [24]crown-8 framework with increasing numbers of benzo rings is observed to lower the stability constants (K(a)'S) from >103 to ~0 M-1 in acetonitrile. A pronounced decrease in K(a) values also occurs when the [24]crown-8 constitution is expanded to give a macroring containing 25 atoms a modification that not only increases the size of the macrocyclic cavity but also disrupts the O-C-C-O repeating unit in the macrocycle's backbone.

AB - A range of crown ethers with either [24]crown-8 or [25]crown-8 constitutions have been demonstrated to form pseudorotaxanes with para- disubstituted dibenzylammonium ions, both in solution and in the 'gas phase' by 1H NMR spectroscopy and liquid secondary ion mass spectrometry, respectively. Substitution of the [24]crown-8 framework with increasing numbers of benzo rings is observed to lower the stability constants (K(a)'S) from >103 to ~0 M-1 in acetonitrile. A pronounced decrease in K(a) values also occurs when the [24]crown-8 constitution is expanded to give a macroring containing 25 atoms a modification that not only increases the size of the macrocyclic cavity but also disrupts the O-C-C-O repeating unit in the macrocycle's backbone.

KW - Crown ethers

KW - Pseudorotaxanes

KW - Substituted ammonium ion binding

KW - Supramolecular chemistry

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U2 - 10.1016/S0040-4039(99)00553-5

DO - 10.1016/S0040-4039(99)00553-5

M3 - Article

AN - SCOPUS:0033531989

SN - 0040-4039

VL - 40

SP - 3661

EP - 3664

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

Abstract

Keywords

ASJC Scopus subject areas

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