A new slippage synthesis

Peter R. Ashton; Matthew C T Fyfe; Cesare Schiavo; J. Fraser Stoddart; Andrew J P White; David J. Williams

doi:10.1016/S0040-4039(98)01071-5

A new slippage synthesis

Peter R. Ashton, Matthew C T Fyfe, Cesare Schiavo, J. Fraser Stoddart^*, Andrew J P White, David J. Williams

^*Corresponding author for this work

Chemistry

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

28 Scopus citations

Abstract

At elevated temperatures, the crown ether dibenzo[30]crown-10 (DB30C10) slips over the (relatively) bulky 3,5-(t-Bu)₂C₆H₃CH₂ termini of a bisammonium dication-bearing two secondary ammonium centers separated through a p-xylylene spacer-to form primarily a three-component rotaxane-like entity- stabilized by, inter alia, [N⁺-H···O] and [C-H···O] hydrogen bonds- that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the 'gas phase'), ¹H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane- like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.

Original language	English (US)
Pages (from-to)	5455-5458
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(98)01071-5
State	Published - Jul 30 1998

Keywords

Crown Ethers
Pseudorotaxanes
Self-assembly
Supramolecular chemistry

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(98)01071-5

Cite this

@article{1780140709be4571963a2677d0b658ff,

title = "A new slippage synthesis",

abstract = "At elevated temperatures, the crown ether dibenzo[30]crown-10 (DB30C10) slips over the (relatively) bulky 3,5-(t-Bu)2C6H3CH2 termini of a bisammonium dication-bearing two secondary ammonium centers separated through a p-xylylene spacer-to form primarily a three-component rotaxane-like entity- stabilized by, inter alia, [N+-H···O] and [C-H···O] hydrogen bonds- that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the 'gas phase'), 1H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane- like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.",

keywords = "Crown Ethers, Pseudorotaxanes, Self-assembly, Supramolecular chemistry",

author = "Ashton, {Peter R.} and Fyfe, {Matthew C T} and Cesare Schiavo and Stoddart, {J. Fraser} and White, {Andrew J P} and Williams, {David J.}",

year = "1998",

month = jul,

day = "30",

doi = "10.1016/S0040-4039(98)01071-5",

language = "English (US)",

volume = "39",

pages = "5455--5458",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "31",

}

TY - JOUR

T1 - A new slippage synthesis

AU - Ashton, Peter R.

AU - Fyfe, Matthew C T

AU - Schiavo, Cesare

AU - Stoddart, J. Fraser

AU - White, Andrew J P

AU - Williams, David J.

PY - 1998/7/30

Y1 - 1998/7/30

N2 - At elevated temperatures, the crown ether dibenzo[30]crown-10 (DB30C10) slips over the (relatively) bulky 3,5-(t-Bu)2C6H3CH2 termini of a bisammonium dication-bearing two secondary ammonium centers separated through a p-xylylene spacer-to form primarily a three-component rotaxane-like entity- stabilized by, inter alia, [N+-H···O] and [C-H···O] hydrogen bonds- that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the 'gas phase'), 1H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane- like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.

AB - At elevated temperatures, the crown ether dibenzo[30]crown-10 (DB30C10) slips over the (relatively) bulky 3,5-(t-Bu)2C6H3CH2 termini of a bisammonium dication-bearing two secondary ammonium centers separated through a p-xylylene spacer-to form primarily a three-component rotaxane-like entity- stabilized by, inter alia, [N+-H···O] and [C-H···O] hydrogen bonds- that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the 'gas phase'), 1H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane- like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.

KW - Crown Ethers

KW - Pseudorotaxanes

KW - Self-assembly

KW - Supramolecular chemistry

UR - http://www.scopus.com/inward/record.url?scp=0032581523&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032581523&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)01071-5

DO - 10.1016/S0040-4039(98)01071-5

M3 - Article

AN - SCOPUS:0032581523

SN - 0040-4039

VL - 39

SP - 5455

EP - 5458

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

A new slippage synthesis

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this