N-Sulfinylaniline
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]
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| Names | |
|---|---|
| Other names
N-thionylaniline, phenyliminooxosulfurane, N-sulfinylbenzenamine | |
| Identifiers | |
| ECHA InfoCard | 100.013.058 |
CompTox Dashboard (EPA) |
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| 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 | |
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]
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References
- 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.
- Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
- Rajagopalan, S.; Advani, B. G.; Talaty, C. N. (1969). "Diphenylcarbodiimide". Organic Syntheses. 49: 70. doi:10.15227/orgsyn.049.0070..
- 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.
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