Description
We report a novel synthetic route to access N-aryl-4-amino-quinolinium salts via a stereoretentive SNAr-type reaction of amines with atropisomeric N-arylquinolin-4-ones, by in-situ formation of the corresponding chloroquinolinium chloride salt. Investigation into the properties of the chiral salts was carried out using X-ray crystallography, DFT analysis, cyclic voltammetry and UV-vis spectroscopy. They were revealed to possess high rotational barriers (with lifetimes of millennia), new photophysical properties and low oxidation potentials. A neutral axially chiral quinolinimine could be obtained by a simple deprotonation of the quinolinium salt.
This dataset contains computational chemistry outputs associated with the investigation of atropisomerisation processes in selected quinolinium salts (5b, 5c, and 5i) and the corresponding axially chiral imine (6). Specifically, it includes:
Gaussian output files (.log) for ground state and transition state calculations
Cartesian coordinate files (.xyz) corresponding to optimised geometries
The data relate to DFT calculations of enantiomerisation pathways, including optimised ground states and transition states used to determine rotational barriers and assess configurational stability.
Calculations were performed using standard quantum chemical methods (as detailed in the associated publication), and the output files can be opened and analysed using common computational chemistry software such as GaussView, Avogadro, IQmol, or other programs capable of parsing Gaussian log files. The .xyz files provide accessible structural coordinates for visualisation or further computation.
These data enable:
reproduction of reported rotational barriers,
inspection of optimised geometries and transition state structures,
reuse in further computational or mechanistic studies of atropisomerism in quinolinium systems.
More detailed methodological information (e.g. functional, basis set, and computational protocol) is provided in the associated publication and can be supplemented in an accompanying README file.
This dataset contains computational chemistry outputs associated with the investigation of atropisomerisation processes in selected quinolinium salts (5b, 5c, and 5i) and the corresponding axially chiral imine (6). Specifically, it includes:
Gaussian output files (.log) for ground state and transition state calculations
Cartesian coordinate files (.xyz) corresponding to optimised geometries
The data relate to DFT calculations of enantiomerisation pathways, including optimised ground states and transition states used to determine rotational barriers and assess configurational stability.
Calculations were performed using standard quantum chemical methods (as detailed in the associated publication), and the output files can be opened and analysed using common computational chemistry software such as GaussView, Avogadro, IQmol, or other programs capable of parsing Gaussian log files. The .xyz files provide accessible structural coordinates for visualisation or further computation.
These data enable:
reproduction of reported rotational barriers,
inspection of optimised geometries and transition state structures,
reuse in further computational or mechanistic studies of atropisomerism in quinolinium systems.
More detailed methodological information (e.g. functional, basis set, and computational protocol) is provided in the associated publication and can be supplemented in an accompanying README file.
| Date made available | 11 Mar 2026 |
|---|---|
| Publisher | Queen's University Belfast |
| Date of data production | Mar 2026 |
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