Tribenzo[27]crown-9: A new ring for dibenzylammonium rods

Stuart J. Cantrill; Matthew C T Fyfe; Aaron M. Heiss; J. Fraser Stoddart; Andrew J P White; David J. Williams

Tribenzo[27]crown-9: A new ring for dibenzylammonium rods

Stuart J. Cantrill, Matthew C T Fyfe, Aaron M. Heiss, J. Fraser Stoddart^*, Andrew J P White, David J. Williams

^*Corresponding author for this work

Chemistry

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

25 Scopus citations

Abstract

(formula presented) Dibenzylammonium (DBA⁺) ions thread through the cavity of tribenzo[27]crown-9 (TB27C9) to generate [2]pseudorotaxanes that are stabilized principally by hydrogen-bonding interactions. The stabilities and complexation kinetics associated with these pseudorotaxanes depend markedly on the nature of the substituents situated on the phenyl rings of the DBA⁺ ions. For example, the complex formed between TB27C9 and the DBA⁺ ion bearing electron-withdrawing P-CO₂Me substituents is stronger than that obtained from TB27C9 and the "parent", unsubstituted DBA⁺ ion itself. Furthermore, the "parent" complex equilibrates much more rapidly with its uncomplexed components than do the complexes generated from TB27C9 and substituted DBA ions.

Original language	English (US)
Pages (from-to)	61-64
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	1
State	Published - Jan 1 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Tribenzo[27]crown-9: A new ring for dibenzylammonium rods",

abstract = "(formula presented) Dibenzylammonium (DBA+) ions thread through the cavity of tribenzo[27]crown-9 (TB27C9) to generate [2]pseudorotaxanes that are stabilized principally by hydrogen-bonding interactions. The stabilities and complexation kinetics associated with these pseudorotaxanes depend markedly on the nature of the substituents situated on the phenyl rings of the DBA+ ions. For example, the complex formed between TB27C9 and the DBA+ ion bearing electron-withdrawing P-CO2Me substituents is stronger than that obtained from TB27C9 and the {"}parent{"}, unsubstituted DBA+ ion itself. Furthermore, the {"}parent{"} complex equilibrates much more rapidly with its uncomplexed components than do the complexes generated from TB27C9 and substituted DBA ions.",

author = "Cantrill, {Stuart J.} and Fyfe, {Matthew C T} and Heiss, {Aaron M.} and Stoddart, {J. Fraser} and White, {Andrew J P} and Williams, {David J.}",

year = "2000",

month = jan,

day = "1",

language = "English (US)",

volume = "2",

pages = "61--64",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Tribenzo[27]crown-9

T2 - A new ring for dibenzylammonium rods

AU - Cantrill, Stuart J.

AU - Fyfe, Matthew C T

AU - Heiss, Aaron M.

AU - Stoddart, J. Fraser

AU - White, Andrew J P

AU - Williams, David J.

PY - 2000/1/1

Y1 - 2000/1/1

N2 - (formula presented) Dibenzylammonium (DBA+) ions thread through the cavity of tribenzo[27]crown-9 (TB27C9) to generate [2]pseudorotaxanes that are stabilized principally by hydrogen-bonding interactions. The stabilities and complexation kinetics associated with these pseudorotaxanes depend markedly on the nature of the substituents situated on the phenyl rings of the DBA+ ions. For example, the complex formed between TB27C9 and the DBA+ ion bearing electron-withdrawing P-CO2Me substituents is stronger than that obtained from TB27C9 and the "parent", unsubstituted DBA+ ion itself. Furthermore, the "parent" complex equilibrates much more rapidly with its uncomplexed components than do the complexes generated from TB27C9 and substituted DBA ions.

AB - (formula presented) Dibenzylammonium (DBA+) ions thread through the cavity of tribenzo[27]crown-9 (TB27C9) to generate [2]pseudorotaxanes that are stabilized principally by hydrogen-bonding interactions. The stabilities and complexation kinetics associated with these pseudorotaxanes depend markedly on the nature of the substituents situated on the phenyl rings of the DBA+ ions. For example, the complex formed between TB27C9 and the DBA+ ion bearing electron-withdrawing P-CO2Me substituents is stronger than that obtained from TB27C9 and the "parent", unsubstituted DBA+ ion itself. Furthermore, the "parent" complex equilibrates much more rapidly with its uncomplexed components than do the complexes generated from TB27C9 and substituted DBA ions.

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M3 - Article

AN - SCOPUS:0002396440

VL - 2

SP - 61

EP - 64

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -

Tribenzo[27]crown-9: A new ring for dibenzylammonium rods

Abstract

ASJC Scopus subject areas

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