Experimental and theoretical investigation on the thermal isomerization reaction of tristriazolotriazines
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Abstract
The isomerization of tristriazolotriazione with tangential substituents to radial isomers occurs in a cascade of three ring opening/rotation/ring closure steps of the central triazine. Donor substitution accelerates the isomerization which can be catalyzed by Brønsted acids. The velocity of the rearrangements drops with each step by a factor of 4, whereas the gain in heat of formation increases. Density functional theory (DFT) calculations led to transition states; their energies correspond to the experimental data. Threefold isomerization strongly affects the mesomorphic properties.
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Journal of physical organic chemistry, 35, 7, John Wiley & Sons, Ltd, Chichester, 2022, https://doi.org/10.1002/poc.4346