Methods, Syntheses and Characterization of Diaryl, Aryl Benzyl, and Dibenzyl Sulfides
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ORIGINAL PAPER
Methods, Syntheses and Characterization of Diaryl, Aryl Benzyl, and Dibenzyl Sulfides Wen‑Yan Zhou1 · Min Chen1 · Pei‑Zhi Zhang1 · Ai‑Quan Jia1 · Qian‑Feng Zhang1 Received: 7 May 2020 / Accepted: 25 August 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract 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. 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.
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13
Vol.:(0123456789)
Journal of Chemical Crystallography
Keywords Aryl benzyl sulfide · Diaryl sulfide · Dibenzyl sulfide · Synthesis · Characterization · Crystal structure
Introduction
Experimental
Sulfides (R-S-R), the R group can be various functional groups, such as alkyl, alkenyl, alkynyl, aryl and benzyl. They are useful starting materials for the synthesis of many organic compounds [1, 2]. Typically, they can be oxidized into sulfoxides or sulfones, which have received extensive attention as essentially synthetic intermediates in some important organic molecule syntheses, such as lansoprazole and omeprazole [3–5]. Due to the diversity of its own functional groups and the substitution of different functional groups, such as nitro, amino, chloro and alkyl, the free combination makes a wide range of sulfides, accordingly their synthetic methods are different. However, traditional methods for formation of C–S bond have some problems such as tedious reaction operation, unfriendly ecological environment, excessive raw materials, high toxicity and expensive catalysts [6]. Recently, several new synthetic methods of sulfides have been explored [7, 8]. Herein,
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