Synthesis and Structural Characterization of a New 1,2,3-Triazole Derivative of Pentacyclic Triterpene

The new 30-substituted triazole derivative of 3,28-O,O '-diacetylbetulin was obtained in the copper(I) catalyzed azide-alkyne cycloaddition (CuAAC). The title compound was characterized by NMR, IR, HR-MS, and X-ray diffraction techniques. The X-ray diffraction study showed that the 1,2,3-triazole derivative crystallizes in the orthorhombic space group P2(1)2(1)2(1), Z = 4, and unit cell parameters are as follows a = 9.4860(10) angstrom, b = 13.9440(2) angstrom, and c = 30.2347(4) angstrom. The molecular packing is stabilized by intermolecular hydrogen interactions C-H horizontal ellipsis O. The Hirshfeld surface analysis showed the presence of the O horizontal ellipsis H interactions with a percentage of the 16.5% in the total Hirshfeld area. The MEP analysis showed that the nucleophilic regions are located near the oxygen atoms of the acyl and carbonyl groups of betulin moiety and the sulfur atom in the triazole linker. The HOMO and LUMO orbitals are located near the triazole moiety. The obtained results indicated that this new betulin derivative is more reactive with electrophilic than nucleophilic molecules.