Effects of chlorine and nitro groups on the crystal structure of novel 4-quinolinone derivatives from sulfonamide chalcone

Abstract

This study explores the impact of introducing chlorine and nitro groups into two novel quinolone derivatives, (E)-3-(4-nitrobenzylidene)-2-(3-nitrophenyl)-2,3-dihydro-1-(phenylsulfonyl)-quinolin-4(1H)-one (NPQ) and (E)-3-(4-chlorobenzylidene)-2-(3-nitrophenyl)-2,3-dihydro-1-(phenylsulfonyl)-quinolin-4(1H)-one (CPQ), using experimental techniques and density functional theory (DFT). The research focuses on crystalline packing, conformational changes, and intermolecular interactions. The investigation reveals that weak non-classical hydrogen interactions, hydrophobic, and CH···π interactions, predominantly stabilize the crystal structures. These interactions, quantified through a Hirshfeld surface analysis. Additionally, the Fukui function analysis indicates antioxidant potential in the crystals. NPQ and CPQ exhibit a small energy gap, implying low kinetic stability, high reactivity, and reduced resistance to charge transfer when compared. These findings provide valuable insights into the structural and electronic properties of these quinolone derivatives, aiding the design of novel compounds with desired characteristics and applications. The DFT analysis utiliazsed the M062-X functional and the 6–311++G(d,p) basis set in the Gaussian 09 package, and the result was visualized using the GaussView software.