Multifaceted study of a pyrimidine sulfonamide derivative: structure, reactivity, optoelectronics, and bioactivity

Pyrimidinesulfonamide derivatives have garnered significant interest owing to their broad spectrum of applications in pharmaceutical development and optoelectronic device engineering. However, despite their potential, comprehensive studies elucidating the structural stability, electronic properties, and reactivity of these compounds remain scarce, limiting the rational design of functional materials in these fields. In this work, we address this critical knowledge gap by synthesizing and characterizing N-(5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (NMMS), integrating both experimental and advanced computational approaches. Single-crystal X-ray diffraction revealed a monoclinic Pbca space group stabilized by intramolecular C–H···Br interactions. Density functional theory (DFT) analyses of molecular electrostatic potential (MEP), average local ionization energies, Fukui functions, and non-covalent interactions (RDG), topological analysis (ELF, LOL) provided detailed insight into electronic distribution and reactive sites previously unreported for the title compound. Additionally, we computed bond dissociation energies, and nonlinear optical (NLO) properties demonstrating NMMS’s chemical stability and optoelectronic potential. Excited-state calculations (ADC(2)) revealed a small singlet–triplet energy gap (ΔES1−T1