Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches
Poster Number
6
Introduction/Abstract
Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur.
Purpose
Exploring other nitrogen linked-cyclohexanol derivatives, like triazoles, could potentially give new models for conformational switches. The triazole substituent is unique because of the numerous attachments that can be linked to the alkyne before synthesis.
Method
Conformational equilibria of the triazolyl-cyclohexanol derivatives were analyzed by 1H NMR. The coupling width of the signal for the hydrogen, adjacent to the carbon on which the triazole ring is attached, was measured and compared to standard models that have their substituents in either the axial or equatorial position.
Results
The triazolyl substituent was shown to have a substantial conformational energy and to always shift the equilibrium toward the conformation, in which it occupies an equatorial position.
Significance
Triazolyl-cyclohexanols could be used as conformational locks in models that prefer to occupy the equatorial position.
Location
DUC Ballroom A&B
Format
Poster Presentation
Poster Session
Afternoon
Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches
DUC Ballroom A&B
Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur.
