Assembly and dissociation of α-cyclodextrin [2]pseudorotaxanes with α,ω-bis(N-(N,N′-dimethylethylenediamine)alkane threads

Victor X. Jin; Donal H. Macartney; Erwin Buncel

doi:10.1007/s10847-005-2065-0

Assembly and dissociation of α-cyclodextrin [2]pseudorotaxanes with α,ω-bis(N-(N,N′-dimethylethylenediamine)alkane threads

Victor X. Jin, Donal H. Macartney, Erwin Buncel

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

8 Scopus citations

Abstract

A series of novel bischelate bridging ligands, CH₃NH(CH ₂)₂N(CH₃)(CH₂) _n N(CH₃)(CH₂)₂NHCH₃ (n = 9, 10, 11, and 12) were synthesized as hydrochloride salts and characterized by elemental analyses, electrospray mass spectrometry, and ¹H and ¹³C NMR spectroscopy. These ligands form [2]pseudorotaxanes with α-cyclodextrin (α-CD) and the stability constants have been determined from ¹H NMR titrations in D₂O. The kinetics and mechanism of the assembly and dissociation of a [2]pseudorotaxane in which α-CD has been threaded by the CH₃NH₂(CH ₂)₂N(CH₃)(CH₂)₁₂N(CH ₃)(CH₂)₂NH₂CH ₃ ²⁺ ligand were determined in aqueous solution using ¹H NMR spectroscopy. A weak inclusion of the dimethylethylenediamine end group precedes the passage of the α-CD onto the hydrophobic dodecamethylene chain.

Original language	English (US)
Pages (from-to)	197-203
Number of pages	7
Journal	Journal of Inclusion Phenomena
Volume	53
Issue number	3
DOIs	https://doi.org/10.1007/s10847-005-2065-0
State	Published - Nov 2005
Externally published	Yes

Keywords

Assembly
Cyclodextrin
Dissociation
Kinetics
Pseudorotaxane

ASJC Scopus subject areas

Food Science
Chemistry(all)
Condensed Matter Physics

Access to Document

10.1007/s10847-005-2065-0

Cite this

@article{af0850e10d5349858033d7b4e1f42ad4,

title = "Assembly and dissociation of α-cyclodextrin [2]pseudorotaxanes with α,ω-bis(N-(N,N′-dimethylethylenediamine)alkane threads",

abstract = "A series of novel bischelate bridging ligands, CH3NH(CH 2)2N(CH3)(CH2) n N(CH3)(CH2)2NHCH3 (n = 9, 10, 11, and 12) were synthesized as hydrochloride salts and characterized by elemental analyses, electrospray mass spectrometry, and 1H and 13C NMR spectroscopy. These ligands form [2]pseudorotaxanes with α-cyclodextrin (α-CD) and the stability constants have been determined from 1H NMR titrations in D2O. The kinetics and mechanism of the assembly and dissociation of a [2]pseudorotaxane in which α-CD has been threaded by the CH3NH2(CH 2)2N(CH3)(CH2)12N(CH 3)(CH2)2NH2CH 3 2+ ligand were determined in aqueous solution using 1H NMR spectroscopy. A weak inclusion of the dimethylethylenediamine end group precedes the passage of the α-CD onto the hydrophobic dodecamethylene chain.",

keywords = "Assembly, Cyclodextrin, Dissociation, Kinetics, Pseudorotaxane",

author = "Jin, {Victor X.} and Macartney, {Donal H.} and Erwin Buncel",

note = "Funding Information: Financial support of this research by the Natural Sciences and Engineering Research Council of Canada (to D.H.M. and E.B.) and the Government of Ontario, Ministry of Training, Colleges, and Universities (to V.X.J.) is gratefully acknowledged.",

year = "2005",

month = nov,

doi = "10.1007/s10847-005-2065-0",

language = "English (US)",

volume = "53",

pages = "197--203",

journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",

issn = "1388-3127",

publisher = "Kluwer Academic Publishers",

number = "3",

}

TY - JOUR

T1 - Assembly and dissociation of α-cyclodextrin [2]pseudorotaxanes with α,ω-bis(N-(N,N′-dimethylethylenediamine)alkane threads

AU - Jin, Victor X.

AU - Macartney, Donal H.

AU - Buncel, Erwin

N1 - Funding Information: Financial support of this research by the Natural Sciences and Engineering Research Council of Canada (to D.H.M. and E.B.) and the Government of Ontario, Ministry of Training, Colleges, and Universities (to V.X.J.) is gratefully acknowledged.

PY - 2005/11

Y1 - 2005/11

N2 - A series of novel bischelate bridging ligands, CH3NH(CH 2)2N(CH3)(CH2) n N(CH3)(CH2)2NHCH3 (n = 9, 10, 11, and 12) were synthesized as hydrochloride salts and characterized by elemental analyses, electrospray mass spectrometry, and 1H and 13C NMR spectroscopy. These ligands form [2]pseudorotaxanes with α-cyclodextrin (α-CD) and the stability constants have been determined from 1H NMR titrations in D2O. The kinetics and mechanism of the assembly and dissociation of a [2]pseudorotaxane in which α-CD has been threaded by the CH3NH2(CH 2)2N(CH3)(CH2)12N(CH 3)(CH2)2NH2CH 3 2+ ligand were determined in aqueous solution using 1H NMR spectroscopy. A weak inclusion of the dimethylethylenediamine end group precedes the passage of the α-CD onto the hydrophobic dodecamethylene chain.

AB - A series of novel bischelate bridging ligands, CH3NH(CH 2)2N(CH3)(CH2) n N(CH3)(CH2)2NHCH3 (n = 9, 10, 11, and 12) were synthesized as hydrochloride salts and characterized by elemental analyses, electrospray mass spectrometry, and 1H and 13C NMR spectroscopy. These ligands form [2]pseudorotaxanes with α-cyclodextrin (α-CD) and the stability constants have been determined from 1H NMR titrations in D2O. The kinetics and mechanism of the assembly and dissociation of a [2]pseudorotaxane in which α-CD has been threaded by the CH3NH2(CH 2)2N(CH3)(CH2)12N(CH 3)(CH2)2NH2CH 3 2+ ligand were determined in aqueous solution using 1H NMR spectroscopy. A weak inclusion of the dimethylethylenediamine end group precedes the passage of the α-CD onto the hydrophobic dodecamethylene chain.

KW - Assembly

KW - Cyclodextrin

KW - Dissociation

KW - Kinetics

KW - Pseudorotaxane

UR - http://www.scopus.com/inward/record.url?scp=24644494820&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=24644494820&partnerID=8YFLogxK

U2 - 10.1007/s10847-005-2065-0

DO - 10.1007/s10847-005-2065-0

M3 - Article

AN - SCOPUS:24644494820

SN - 1388-3127

VL - 53

SP - 197

EP - 203

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

IS - 3

ER -

Assembly and dissociation of α-cyclodextrin [2]pseudorotaxanes with α,ω-bis(N-(N,N′-dimethylethylenediamine)alkane threads

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this