Palladium-catalyzed synthesis of 5-(arylated) pyrimidines, their characterization, electronic communication, and non-linear optical evaluations

The synthesis of pyrimidine and its derivatives is a dynamic emerging area of research due to its pharmaceutical, agricultural, and photonic applications. In this study, new derivatives of pyrimidine 5-([1, 1'-biphenyl]-4-yl) pyrimidine (3a), 5-[4-(methylsulfanyl)phenyl]pyrimidine (3b), 5-(4(trifluoromethoxy)phenyl)pyrimidine (3c), and 5-(2,3-dichlorophenyl)pyrimidine (3d) were synthesized through Suzuki-Miyaura coupling, and assessed by H-1 NMR, C-13 NMR, FT-IR, and UV/Visible analysis. Furthermore, computational study such as spectroscopic, frontier molecular orbital (FMO), natural bond orbital (NBO), and the molecular electrostatic potential (MEP) was performed at M06/6-311G** to obtain comprehensive insights into electronic communications and the structural property relationship for synthesized compounds. The maximum experimental absorption (lambda(Exp)) for 3a to 3d was obtained at 260, 301, 248, and 233 nm, respectively in methanol, which displayed good agreement with theoretical (lambda(DFT)) result 279, 298, 247, and 233 nm, respectively. Moreover, different functional(s) such as HF, M06, M062X, CAM-B3LYP, and LC-BLYP with basis sets 6-311G** were utilized to compute the average polarizability <alpha >, total dipole moment (mu(tot)), and hyperpolarizability (ss(tot)) values. Among the tested methods, highest mu tot value (3.5465 D) was observed for 3d, and the lowest value (0.2680 D) for 3c through HF method. Consequently, the LC-BLYP method also showed the highest mu tot value (3.4689 D) for 3d and the lowest value (0.3123 D) of 3c. Moreover, other methods: CAM-B3LYP, M062X, and M06 showed almost similar values for all compounds with similar trends. The M06 method showed the largest <alpha > values (190.779, 149.331, 130.430 and 138.964 a.u.) for 3a, 3b, 3c, and 3d, respectively. In contrast, the HF method showed the least <alpha > values (178.166, 140.356, 121.848, and 128.994 a.u.) for 3a, 3b, 3c, and 3d, respectively. The other methods (CAMB3LYP, M062X, and LC-BLYP) indicated nearly parallel <alpha > values. Moreover, the (ss(tot)) values (604.898, 344.234, 41.628, and 299.958 a.u.) obtained with M06 method for 3a, 3b, 3c, and 3d, respectively, were higher compared with urea (ss(tot) = 69.399 a.u.). (C) 2021ElsevierB.V. Allrightsreserved.