''N''-Sulfinylaniline
 | |
| Names | |
|---|---|
| Other names
N-thionylaniline, phenyliminooxosulfurane, N-sulfinylbenzenamine | |
| Identifiers | |
| ECHA InfoCard | 100.013.058 |
| 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). | |
| Infobox references | |
N-Sulfinylaniline is the organosulfur compound with the formula C6H5NSO. It is a straw-colored liquid that is classified as a heterocumulene, being closely related to sulfur dioxide. as well as sulfur diimide, 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
By crystallographic analysis, the C–S=N=O dihedral angle is –1.60°,[4] in keeping with the planar–syn geometry found in a wide range of N-sulfinylimine compounds.[5]
References
- ↑ Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. doi:10.1002/anie.196701491
- ↑ Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227.
- ↑ S. Rajagopalan, B. G. Advani, and C. N. Talaty "Diphenylcarbodiimide" Org. Synth. 1969, volume 49, p. 70. doi:10.15227/orgsyn.049.0070.
- ↑ R. M. Romano, C. O. Della Védova, and R. Boese "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 1999, volume 475, issue 1, pp. 1–4 doi:10.1016/S0022-2860(98)00439-6.
- ↑ R. M. Romano and C. O. Della Védova "N-Sulfinylimine compounds, R–N=S=O: a chemistry family with strong temperament" Journal of Molecular Structure 2000, volume 522, issues 1–3, pp. 1–26. doi:10.1016/S0022-2860(99)00453-6.
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