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[2] and a ligand in organometallic chemistry.[3]

Synthesis and structure

It is prepared by treating aniline with thionyl chloride:[4]

3 PhNH2 + SOCl2 → PhNSO + 2 [PhNH3]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°.[5]

References

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1032. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Kresze, G.; Wucherpfennig, W. (1967). "New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide". Angewandte Chemie International Edition in English. 6 (2): 149–167. doi:10.1002/anie.196701491. PMID 4962859.
  3. ^ Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
  4. ^ Rajagopalan, S.; Advani, B. G.; Talaty, C. N. (1969). "Diphenylcarbodiimide". Organic Syntheses. 49: 70. doi:10.15227/orgsyn.049.0070..
  5. ^ Romano, R.M; Della Védova, C.O; Boese, R. (1999). "A Solid State Study of the Configuration and Conformation of O=S=N–R (R=C6H5 and C6H3(CH3–CH2)2-2,6)". Journal of Molecular Structure. 475 (1): 1–4. Bibcode:1999JMoSt.475....1R. doi:10.1016/S0022-2860(98)00439-6.
Allikas: https://en.wikipedia.org/wiki/Sulfinylaniline
No tags for this post.