Chiral recognition for the complexation dynamics of β-cyclodextrin with the enantiomers of 2-naphthyl-1-ethanol
| dc.contributor.author | Tang, Hao | |
| dc.contributor.author | Sutherland, Andria S. M. | |
| dc.contributor.author | Osusky, Lana M. | |
| dc.contributor.author | Li, Yan | |
| dc.contributor.author | Holzwarth, Josef F. | |
| dc.contributor.author | Bohne, Cornelia | |
| dc.date.accessioned | 2016-11-04T22:00:51Z | |
| dc.date.available | 2016-11-04T22:00:51Z | |
| dc.date.copyright | 2014 | en_US |
| dc.date.issued | 2014-02 | |
| dc.description.abstract | The focus of this study is to understand the origin of the chiral recognition for a host–guest system containing complexes with different stoichiometries. Each enantiomer of 2-naphthyl-1-ethanol forms two different 1 : 1 complexes with β-cyclodextrin, leading to the formation of three different 2 : 2 complexes. One of these 2 : 2 complexes leads to excimer emission of the guest. Fluorescence studies were employed to determine the binding isotherms for the 1 : 1 and 2 : 2 complexes. No chiral discrimination was directly observed for the formation of the 1 : 1 complexes, while higher equilibrium constants (29% from binding isotherms and 40% from kinetic studies) were observed for the formation of the 2 : 2 complexes with (R)-2-naphthyl-1-ethanol when compared to the formation of the 2 : 2 complexes formed from (S)-2-naphthyl-1-ethanol. The relaxation kinetics was studied using stopped-flow experiments. The formation of the 2 : 2 complexes was followed by detecting the excimer emission from one of the 2 : 2 complexes. The relaxation kinetics was faster for (S)-2-naphthyl-1-ethanol, where a higher dissociation rate constant, by 47%, was observed, suggesting that the chiral discrimination occurs because the interaction between two cyclodextrins is more favorable for the complexes containing (R)-2-naphthyl-1-ethanol when compared to (S)-2-naphthyl-1-ethanol. The same overall equilibrium constants were observed for the 1 : 1 complexes with both enantiomers showing that at a given cyclodextrin concentration the sum of the two types of 1 : 1 complexes is the same for both enantiomers. However, analysis of the binding isotherms indicates that the ratio between the two different 1 : 1 complexes for each enantiomer was different for (R)- and (S)-2-naphthyl-1-ethanol. | en_US |
| dc.description.reviewstatus | Reviewed | en_US |
| dc.description.scholarlevel | Faculty | en_US |
| dc.identifier.citation | Tang et al., (2014). Chiral recognition for the complexation dynamics of β- cyclodextrin with the enantiomers of 2-naphthyl-1-ethanol. Photochemical & Photobiological Sciences, 13(2), 358-369. doi:10.1039/c3pp50298h | en_US |
| dc.identifier.uri | http://dx.doi.org/10.1039/c3pp50298h | |
| dc.identifier.uri | http://hdl.handle.net/1828/7618 | |
| dc.language.iso | en | en_US |
| dc.publisher | Photochemical & Photobiological Sciences | en_US |
| dc.rights | Attribution 2.5 Canada | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/2.5/ca/ | * |
| dc.subject.department | Department of Chemistry | |
| dc.title | Chiral recognition for the complexation dynamics of β-cyclodextrin with the enantiomers of 2-naphthyl-1-ethanol | en_US |
| dc.type | Article | en_US |