Abstract
The planar structure of 1,2,5- and 1,3,4-triazoles were manipulated through (i) the replacement of 1-nitrogen in the ring by other nitrogen family atoms, and (ii) joining two triazoles from the 1–1 position at the rings. Calculated geometrical parameters of those manipulated triazole derivatives in both planar and puckered configurations revealed that 1-nitrogen substituted triazole structures have lost their planarity. Due to adiabatic potential energy surface cross-section and electron configurations of the puckered compounds, electron excitation from the 1A1 ground to low-lying 1B1 excited states is the reason for planar instability in the series which was formulated as the PJTE (1A1 + 1B1 + 2A1) ⊗b1 problem. Moreover, joining two triazole rings via 1–1 ring positions affected the stability of 1,2,5- and 1,3,4-triazole rings and amplify the puckering in other bicyclic tripnigole series. Due to the biological activities of triazole, manipulation of its structure may help us to discover more potent and specific triazole drugs or consequently, reduce its side effects.
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Author expresses his gratitude to Yazd Branch, Islamic Azad University for the financial support of this research. This research has been enabled in part with support Westgrid (http://www.westgrid.ca) and Compute/Calcul Canada (http://www.computecanada.ca).
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Ilkhani, A.R. Manipulation of planar structure of 1,2,5- and 1,3,4-triazoles and the pseudo Jahn–Teller effect in their 1-pnictogen derivatives. Chem. Pap. 73, 85–94 (2019). https://doi.org/10.1007/s11696-018-0567-7
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DOI: https://doi.org/10.1007/s11696-018-0567-7