Synthesis and supramolecular self-assembly of thioxothiazolidinone derivatives driven by H-bonding and diverse π–hole interactions: A combined experimental and theoretical analysis

摘要: Abstract Two new 3-aryl-5-(4-nitrobenzylidene)-2-thioxothiazolidin-4-one derivatives ( 1 & 2 ) were synthesized by the Knoevenagel condensation reaction of 3-(4-aryl)-2-thioxo-1,3-thiazolidin-4-ones with 4-nitrobenzaldehyde. Both products isolated as orange crystalline solids in good yields and fully characterized analytical, spectroscopic structural methods. The interesting supramolecular assemblies title compounds observed solid state analyzed Density Functional Theory (DFT) calculations (M06-2X/def2-TZVP), Molecular Electrostatic Potential (MEP) surfaces means Bader's theory “atoms-in-molecules” (AIM) NCIplot. computation energy features diverse noncovalent interactions including C H⋯π, π⋯π lp⋯π-hole revealed their conspicuous role stabilization three-dimensional frameworks for both addition to H⋯O/S H-bonding interactions.