15N NMR spectroscopic and theoretical GIAO-DFT studies for the unambiguous characterization of disubstituted 1,2,3-triazoles

Abstract

The 1,2,3-triazole ring has recently attracted a renewed interest as a structural scaffold with many applications in different fields. However, very often, the unambiguous assignment of the correct structure is not an easy task, and the development of robust characterization methodologies is needed. Herein, the three possible isomeric forms of disubstituted 1,2,3-triazole (1,4- or 1,5- or 2,4-disubstituted derivatives) have been characterized and distinguished by routine ¹H/¹⁵N gHMBC experiments at ¹⁵N natural abundance. The calculated (GIAO-B3LYP/6-311++G**) ¹⁵N NMR chemical shifts showed good agreement with the experimental values, further supporting their unambiguous structural characterization.