N-Sulfinylaniline Explained

N-Sulfinylaniline is the organosulfur compound with the formula C6H5NSO. It is a straw-colored liquid. N-Sulfinylaniline is an example of a sulfinylamine. It is a dienophile[1] and a ligand in organometallic chemistry.[2]

Synthesis and structure

It is prepared by treating aniline with thionyl chloride:[3]

3 PhNH2 + SOCl2 → PhNSO + 2 [PhNH<sub>3</sub>]Cl

X-ray crystallographic analysis confirms that N-sulfinylaniline is structurally related to sulfur dioxide as well as sulfur diimide. The C–S=N=O dihedral angle is –1.60°.[4]

References

  1. 10.1002/anie.196701491. New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide. 1967. Kresze. G.. Wucherpfennig. W.. Angewandte Chemie International Edition in English. 6. 2. 149–167. 4962859.
  2. Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
  3. 10.15227/orgsyn.049.0070. Diphenylcarbodiimide. Organic Syntheses. 1969. 49. 70. S.. Rajagopalan. B. G.. Advani. C. N.. Talaty. .
  4. 10.1016/S0022-2860(98)00439-6. A Solid State Study of the Configuration and Conformation of O=S=N–R (R=C6H5 and C6H3(CH3–CH2)2-2,6). 1999. Romano. R.M. Della Védova. C.O. Boese. R.. Journal of Molecular Structure. 475. 1. 1–4. 1999JMoSt.475....1R.

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