Efficient Synthesis, SC-XRD, and Theoretical Studiesof O ‑Benzenesulfonylated Pyrimidines: Roleof Noncovalent Interaction Influence in Their Supramolecular Network
2020
Crystalline organic
compounds, 2-amino-6-methylpyrimidin-4-yl benzenesulfonate
(AMPBS) and 2,6-diaminopyrimidin-4-yl benzenesulfonate (DAPBS), were
prepared via O-benzenesulfonylation of 2-amino-6-methylpyrimidin-4-ol
1 and 2,6-diaminopyrimidin-4-ol 2, respectively. The structural interpretations
were achieved unambiguously by single-crystal X-ray diffraction (SC-XRD)
analysis. The Hirshfeld surface study showed that C–H···O,
N–H···N, and especially C–H···C
hydrogen bond interactions are the key contributors to the intermolecular
stabilization in the crystal. Density functional theory (DFT) studies
were used to obtain a better understanding of natural bond orbitals
(NBOs) and nonlinear optical (NLO) analysis for AMPBS and DAPBS at
the B3LYP/6-311G(d,p) level. The time-dependent density functional
theory (TD-DFT)/CAM-B3LYP/6-311G(d,p) level was employed for frontier
molecular orbital analysis of both compounds. DFT-based vibrations
for C–H, CN, N–H, and stretching for C–C
were found to be in good agreement with the experimental data. Overall,
the theoretical findings were acquired in correspondence to the SC-XRD-based
parameters. Intracharge transfer occurred in AMPBS and DAPBS compounds,
which was evaluated through FMO activity. Global reactivity indices
had been acquired utilizing energies of HOMO–LUMO orbitals.
Overall, the theoretical findings related to AMPBS and DAPBS consist
of promising correspondence to experimental findings. The theoretical-based
study also exhibited that both AMPBS and DAPBS compounds contain promising
NLO features.
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