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N-Sulfinylaniline

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N-Sulfinylaniline
Names
Other names
N-thionylaniline, phenyliminooxosulfurane, N-sulfinylbenzenamine
Identifiers
ECHA InfoCard 100.013.058 Edit this at Wikidata
Properties
C6H5NSO
Molar mass 139.18
Appearance yellowish oil
Density 1.236 g/mL
Boiling point 88–95 °C (17–20 mm.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Sulfinylaniline is the organosulfur compound with the formula C6H5NSO. It is a straw-colored liquid. N-Sulfinylaniline is an example of a sulfinylamine, a heterocumulene. 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 [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°,[4]

References

  1. ^ 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.
  2. ^ Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
  3. ^ Rajagopalan, S.; Advani, B. G.; Talaty, C. N. (1969). "Diphenylcarbodiimide". Organic Syntheses. 49: 70. doi:10.15227/orgsyn.049.0070..
  4. ^ 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.