Methods, Syntheses and Characterization of Diaryl, Aryl Benzyl, and Dibenzyl Sulfides

Twenty-four aryl benzyl sulfides, diaryl sulfides and dibenzyl sulfides were synthesized by four methods and characterized by 1 H 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 P 2 1 / 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 P ī 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 P 2 1 2 1 2 1 , 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 . Graphic Abstract 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.