Abstract

2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl naphthalene-2-sulfonate was obtained as a result of the reactions of 5-amino-2-sulfanylbenzimidazole with 2-(2-naphthylsulfonyloxy)benzaldehyde. The newly synthesized compound was characterized using IR, ¹H and ¹³C NMR spectroscopy. Theoretical investigations of the thione–thiol tautomerism of the molecule were performed using DFT/ B3LYP calculations with the 6-311++G(d,p) basis set. The NMR chemical shifts were calculated by the gauge-invariant atomic orbital (GIAO) method and compared with the experimental data. Additionally, the frontier molecular orbital (HOMO-LUMO), MEP, and NLO analyses were performed for the optimized structure. The NLO analysis showed that the thiol form of the molecule is more stable than the thione form and is a good non-linear optical compound.

中文翻译：

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2-[（2-硫烷基-1 H-苯并[d]咪唑-5-基）亚氨基甲基]苯基萘-2-磺酸酯的合成，光谱和计算分析

摘要

5-氨基-2-硫烷基苯并咪唑与2-（2）的反应，得到了2-[（（2-硫烷基-1 H-苯并[ d ]咪唑-5-基]亚氨基甲基]苯基]萘-2-磺酸盐。 -萘磺酰氧基）苯甲醛。使用IR，¹ H和¹³对新合成的化合物进行表征13 C NMR光谱。使用6-311 ++ G（d，p）基集进行DFT / B3LYP计算，对分子的硫酮-硫醇互变异构进行了理论研究。NMR化学位移是通过轨距不变原子轨道（GIAO）方法计算的，并与实验数据进行了比较。此外，还针对优化结构进行了前沿分子轨道（HOMO-LUMO），MEP和NLO分析。NLO分析表明，分子的硫醇形式比硫酮形式更稳定，并且是良好的非线性光学化合物。