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6th May 2012 @ 18:16
Spectroscopic Method: MS-ESI
Substituent: Nitro
MS Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one:

MS Spectrum of 3-(1-Nitrophenyl) 1, 3-Dihydroindol-2H-one

The mass spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one has been obtained by negative electrospray ionization (ESI). The peak at m/e = 265.2 confirms the molecular mass of this compound as the molecular ion gains a proton.

Interpretation of MS Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one:

Peak PositionDiff. between molecular mass and peakSuspected molecules or ionsInference
265.2265 - 264 = 1(M+H)+Parent compound plus a proton
Attached Files
6th May 2012 @ 17:14
Spectroscopic Method: HPLC
Substituent: Nitro
HPLC Chromatogram of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one:

HPLC Chromatogram of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one

The sharp peak at the retention time of 6.074 confirms the presence of a single isomer in this compound while the small peak at 5.832 retention time indicates trace of impurities. The percentage area peak of this compound confirms its percentage yield to be 67.58% against its calculated value of 70%.
Attached Files
6th May 2012 @ 16:30
Spectroscopic Method: ATIR-FT-IR
Substituent: Nitro
ATIR-FT-IR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one

ATIR-FT-IR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one

Interpretation of ATIR-FT-IR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one:

ATIRFT-IR Wave Number (cm-1)AssignmentRemarks
3073Aromatic C-H stretching vibration (v(C-H)C-H aromatic stretching in the region 3100-3000cm-1
2961C-H stretching vibrationsDue to CH3 group in the aromatic ring
2842C-H stretching vibrationsDue to CH2 groups in the region 2925-2850cm-1
1697C=O stretching vibration (v(C=O)Due to the carbonyl functional group
1512Phenyl ringsDue to the vibration of phenyl group at 1450-1600cm-1 region.
1403C-NO2Due to asymmetrical and symmetrical stretching of the NO bonds on the region 1390-1340cm-1
1202Aromatic aliphaticVery strong bands on the region 1300-1200cm-1
Attached Files
6th May 2012 @ 15:43
Spectroscopic Method: C-NMR
Substituent: Nitro
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one PDF
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one ascii data
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one Jeol Delta data
13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one JCAMP-DX data

13C NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one peak Chemical Shifts/ppm
39.9, 40.0, 40.2, 77.2, 110.7, 121.5, 122.9, 123.9, 129.9, 130.9, 132.4, 141.9, 143.3, 147.7, 161.1, 169.1 (some quaterneries missing, poor solubility)
Attached Files
3rd May 2012 @ 13:20
Spectroscopic Method: H-NMR
Substituent: Nitro
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one

1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one ascii data
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one mnova data
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one PDF
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one JCAMP-DX data
1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one ChemDoodle spectrum

Interpretation of 1H NMR Spectrum of (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one:

Chemical Shift, ppmMultiplicity, (n+1)Coupling Constant, J HzIntegration, Σ HInference
6.81 - 6.91multiplet 2oxindole hydrogens on C5 and C6
7.21pseudo triplet7.51oxindole hydrogen on C7
7.39pseudo triplet7.51oxindole hydrogen on C4
7.68Singletn/a1vinylic hydrogen on C8
7.80Doublet8.62benzylic hydrogens on C9 and C13
8.34Doublet8.62benzylic hydrogens on C10 and C12
10.70broad singletn/a1amine hydrogen on N1
Attached Files