Conformational mobility in chemically-modified cyclodextrins

Paul Ellwood; Catriona M. Spencer; Neil Spencer; J. Fraser Stoddart; Ryszard Zarzycki

doi:10.1007/BF01053857

Conformational mobility in chemically-modified cyclodextrins

Paul Ellwood, Catriona M. Spencer, Neil Spencer, J. Fraser Stoddart^*, Ryszard Zarzycki

^*Corresponding author for this work

Chemistry

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

24 Scopus citations

Abstract

The observation that per-2,6-O-methyl-3-O-benzoyl-α-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-α-cyclodextrin (3) and some related compounds (7-9) between conformational isomers with averaged C₆ and C₃ molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9° in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species with C₃ molecular symmetry, to +92° in acetone where a species with averaged C₆ symmetry is present.

Original language	English (US)
Pages (from-to)	121-150
Number of pages	30
Journal	Journal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume	12
Issue number	1-4
DOIs	https://doi.org/10.1007/BF01053857
State	Published - Jan 1992

Keywords

Chemically-modified cyclodextrins
NMR spectroscopy
conformational analysis

ASJC Scopus subject areas

Food Science
General Chemistry
Condensed Matter Physics

Access to Document

10.1007/BF01053857

Cite this

@article{fc03aefdb44c43ab880c1a516928f6ea,

title = "Conformational mobility in chemically-modified cyclodextrins",

abstract = "The observation that per-2,6-O-methyl-3-O-benzoyl-α-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-α-cyclodextrin (3) and some related compounds (7-9) between conformational isomers with averaged C6 and C3 molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9° in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species with C3 molecular symmetry, to +92° in acetone where a species with averaged C6 symmetry is present.",

keywords = "Chemically-modified cyclodextrins, NMR spectroscopy, conformational analysis",

author = "Paul Ellwood and Spencer, {Catriona M.} and Neil Spencer and {Fraser Stoddart}, J. and Ryszard Zarzycki",

year = "1992",

month = jan,

doi = "10.1007/BF01053857",

language = "English (US)",

volume = "12",

pages = "121--150",

journal = "Journal of Inclusion Phenomena and Molecular Recognition in Chemistry",

issn = "0923-0750",

publisher = "Springer",

number = "1-4",

}

TY - JOUR

T1 - Conformational mobility in chemically-modified cyclodextrins

AU - Ellwood, Paul

AU - Spencer, Catriona M.

AU - Spencer, Neil

AU - Fraser Stoddart, J.

AU - Zarzycki, Ryszard

PY - 1992/1

Y1 - 1992/1

N2 - The observation that per-2,6-O-methyl-3-O-benzoyl-α-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-α-cyclodextrin (3) and some related compounds (7-9) between conformational isomers with averaged C6 and C3 molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9° in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species with C3 molecular symmetry, to +92° in acetone where a species with averaged C6 symmetry is present.

AB - The observation that per-2,6-O-methyl-3-O-benzoyl-α-cyclodextrin (1) displays some unusual conformational behaviour in solution has led to a detailed investigation by (dynamic) NMR spectroscopy of the equilibration process that occurs in solutions of per-2,3-O-benzoyl-α-cyclodextrin (3) and some related compounds (7-9) between conformational isomers with averaged C6 and C3 molecular symmetries in certain organic solvents such as benzene, dichloromethane, and chloroform. The solvent dependence of the conformational equilibrium is also reflected in a spread of values for the specific optical rotations for 3 from +9° in 1,1,2,2-tetrachloroethane, where there is a degenerate equilibrium between species with C3 molecular symmetry, to +92° in acetone where a species with averaged C6 symmetry is present.

KW - Chemically-modified cyclodextrins

KW - NMR spectroscopy

KW - conformational analysis

UR - http://www.scopus.com/inward/record.url?scp=0039698923&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0039698923&partnerID=8YFLogxK

U2 - 10.1007/BF01053857

DO - 10.1007/BF01053857

M3 - Article

AN - SCOPUS:0039698923

SN - 0923-0750

VL - 12

SP - 121

EP - 150

JO - Journal of Inclusion Phenomena and Molecular Recognition in Chemistry

JF - Journal of Inclusion Phenomena and Molecular Recognition in Chemistry

IS - 1-4

ER -

Conformational mobility in chemically-modified cyclodextrins

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this