Dibenzyl sulfide explained

Dibenzyl sulfide is a symmetrical thioether. It contains two C6H5CH2- (benzyl) groups linked by a sulfide bridge. It is a colorless or white solid that is soluble in nonpolar solvents.

Crystallography

The crystal structure of the solid is of the orthorhombic system with space group Pbcn; number 60. The unit cell dimensions are a=13.991 Å b=11.3985 Å c 7.2081 Å. The molecules in the gas take the same form as in the solid with a C2 symmetry.[1]

Production

Benzyl sulfide is commercially manufactured by treating potassium sulfide with benzyl chloride, followed by distillation of the product.[2] It is also obtainable by desulfurization of dibenzyldisulfide with phosphine reagents.[3]

Notes and References

  1. Hansson . Christian . Dibenzyl sulfide at 150 K . Acta Crystallographica Section E . 19 May 2006 . 62 . 6 . o2377–o2379 . 10.1107/S1600536806017491.
  2. Book: Lewis, R.J. Sr. Hawley's Condensed Chemical Dictionary. 12. New York, NY. Van Nostrand Rheinhold Co. 1993. 137.
  3. Sulfide Synthesis: Benzyl Sulfide. David N. . Harpp. Roger A.. Smith. Org. Synth.. 1978. 58. 138. 10.15227/orgsyn.058.0138.