Twenty-four aryl benzyl sulfides, diaryl sulfides and dibenzyl sulfides were synthesized by four methods and characterized by 1H NMR, FT-IR and Gas chromatography. The reaction conditions of different synthesis methods were studied from the aspects of time, solvent, base and dispersant. The molecular structures of benzylphenyl sulfide (2S), (4-tert-butylbenzyl)(4-methylphenyl) sulfide (4S), (4-methylbenzyl)(4-methylphenyl) sulfide (9S), di(4-methylphenyl) sulfide (11S), (3,5-dimethylphenyl)(4-methyl phenyl) sulfide (15S), and dibenzyl sulfide (19S) [22] have been determined by single-crystal X-ray crystallography. Compounds 2S and 15S crystallize in the monoclinic space group P21/c, with a = 12.278(3), b = 15.894(3), c = 5.6056(11) Å, β = 94.532(2)°, and Z = 4 for 2S, and a = 9.800(9), b = 7.950(7), c = 16.690(15) Å, β = 100.890(12)°, and Z = 4 for 15S. The unit cell of 4S has a triclinic Pī symmetry with the cell parameters a = 6.0436(10), b = 8.7871(14), c = 15.535(2) Å, α = 81.921(2)°, β = 81.977(2)°, γ = 80.889(2)°, and Z = 2. Compounds 9S and 11S both crystallize in the orthorhombic space group P212121, with a = 6.188(3), b = 8.041(4), c = 26.005(14) Å, and Z = 4 for 9S, and a = 5.835(2), b = 8.010(3), c = 25.131(9) Å, and Z = 4 for 11S. Twenty-four aryl sulfide compounds with different substituents were synthesized and characterized, and the molecular structures of six different sulfide compounds have been determined by single-crystal X-ray crystallography.

中文翻译：

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二芳基、芳基苄基和二苄基硫化物的方法、合成和表征

采用4种方法合成了24种芳基苄基硫醚、二芳基硫醚和二苄基硫醚，并通过1H NMR、FT-IR和气相色谱进行了表征。从时间、溶剂、碱和分散剂等方面研究了不同合成方法的反应条件。苄基苯基硫化物(2S)、(4-叔丁基苄基)(4-甲基苯基)硫化物(4S)、(4-甲基苄基)(4-甲基苯基)硫化物(9S)、二(4-甲基苯基)硫化物( 11S)、(3,5-二甲基苯基)(4-甲基苯基)硫化物 (15S) 和二苄基硫化物 (19S) [22] 已通过单晶 X 射线晶体学测定。化合物 2S 和 15S 在单斜空间群 P21/c 中结晶，a = 12.278(3), b = 15.894(3), c = 5.6056(11) Å, β = 94.532(2)°, Z = 4 2S, a = 9.800(9), b = 7.950(7), c = 16.690(15) Å, β = 100.890(12)°, 并且 Z = 4 为 15S。4S 的晶胞具有三斜 Pī 对称性，晶胞参数 a = 6.0436(10), b = 8.7871(14), c = 15.535(2) Å, α = 81.921(2)°, β = 81.977(2) °，γ = 80.889(2)°，Z = 2。化合物 9S 和 11S 均在正交空间群 P212121 中结晶，a = 6.188(3), b = 8.041(4), c = 26.005(14) Å ，对于 9S，Z = 4，对于 11S，a = 5.835(2)，b = 8.010(3)，c = 25.131(9) Å，Z = 4。合成并表征了 24 种不同取代基的芳基硫化物，并通过单晶 X 射线晶体学确定了 6 种不同硫化物的分子结构。化合物 9S 和 11S 均在正交空间群 P212121 中结晶，a = 6.188(3), b = 8.041(4), c = 26.005(14) Å，9S 的 Z = 4，a = 5.835(2) , b = 8.010(3), c = 25.131(9) Å，对于 11S，Z = 4。合成并表征了 24 种不同取代基的芳基硫化物，并通过单晶 X 射线晶体学确定了 6 种不同硫化物的分子结构。化合物 9S 和 11S 均在正交空间群 P212121 中结晶，a = 6.188(3), b = 8.041(4), c = 26.005(14) Å，9S 的 Z = 4，a = 5.835(2) , b = 8.010(3), c = 25.131(9) Å，对于 11S，Z = 4。合成并表征了 24 种不同取代基的芳基硫化物，并通过单晶 X 射线晶体学确定了 6 种不同硫化物的分子结构。