Straightforward synthesis, spectroscopic characterizations and comprehensive DFT calculations of novel 1-ester 4-sulfonamide-1,2,3-triazole scaffolds

Abstract

For the first time, an efficient click azide‒alkyne [3 + 2] cycloaddition reaction for synthesis of new 1-ester 4-sulfonamide-1,2,3-triazole derivatives was developed via a three-component reaction of N-propargylsulfonamides, sodium azide, and α-haloesters in a one pot method. The mild reaction conditions, avoiding the isolation of hazardous organic azides, good yields (65–78%), and commercially available and inexpensive starting materials are advantages of this cycloaddition reaction for synthesis of fine chemicals. The all desired products were characterized by FT-IR, 1H and 13C NMR spectroscopy. The HOMO-LUMO analysis (electrophilicity index), vibrational frequencies (FT-IR), 1H and 13C chemical shift values and Li+ and Na+ ion affinities of a desired product have been also calculated by density functional theory (DFT). Lithium ion affinity of the product was determined as 80.78 kJ/mol higher than its sodium ion affinity. The NICS index was used to confirm of the cation π interaction in complex of the synthesized product with Li+ and Na+ ions.