(NZ)-N-oxido-N-(phenylmethylidene)anilinium

• ChemBase ID: 301842
• Molecular Formular: C13H11NO
• Molecular Mass: 197.23254
• Monoisotopic Mass: 197.08406398
• SMILES: c1ccc(cc1)/C=[N+](/c1ccccc1)\[O-]
• Canonical SMILES: [O-]/[N+](=C\c1ccccc1)/c1ccccc1
• InChI: InChI=1S/C13H11NO/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-11H/b14-11-
• InChIKey: ZEAUJQWDPKRESH-KAMYIIQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (NZ)-N-oxido-N-(phenylmethylidene)anilinium
• IUPAC Traditional name: (NZ)-N-oxido-N-(phenylmethylidene)anilinium
• Synonyms: N,alpha-Diphenyl nitrone; N-α-二苯硝酮

Database IDs

• CAS Number: 1137-96-8
• EC Number: 214-509-2
• MDL Number: MFCD00013895
• Beilstein Number: 608470

CALCULATED PROPERTIES

• Acid pKa: 5.1158533
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.036586
• LogD (pH = 7.4): 2.1827745
• Log P: 0.16140366
• Molar Refractivity: 71.2312 cm^3
• Polarizability: 23.031357 Å^3
• Polar Surface Area: 26.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 113-114°C

Safety Information

• TSCA Listed: 否

Product Information

• Purity: 97%

REFERENCES

• For an example of 1,3-dipolar cycloaddition with an alkene to give an isoxazolidine, see: Org. Synth. Coll., 5, 1124 (1973):
  
• Similarly, regioselective addition to propiolic esters or alkynyl ketones gives isoxazolines: Tetrahedron, 44, 1247 (1988). The regioselectivity of 1,3-dipolar additions of nitrones with electron-deficient alkenes has been studied: J. Org. Chem., 49, 276 (1984).
• Reviews: 1,3-Dipolar cycloadditions of nitrones: Synthesis, 205 (1975); The [3+2] nitrone-olefin cycloaddition reaction: Org. React., 36, 1 (1988); Synthetic applications of nitrones: Org. Prep. Proced. Int., 17, 25 (1985).