Phthalimide

• Formula: C₈H₅NO₂
• Molecular weight: 147.1308
• IUPAC Standard InChI: InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11) Copy

  
• IUPAC Standard InChIKey: XKJCHHZQLQNZHY-UHFFFAOYSA-N Copy
• CAS Registry Number: 85-41-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: 1H-Isoindole-1,3(2H)-dione; Benzoimide; Isoindole-1,3-dione; 1,2-Benzenedicarboximide; 1,3-Isoindolinedione; 2-Diazoindan-1,3-dione; o-Phthalic imide; 1,3-Isoindoledione; Ftalimmide; Phthalimid; Phenylimide; Phthalic dicarboximide; 1,3-Dihydro-2H-isoindole-1,3-dione; NSC 3108; Isoindol-1,3-dione: Folpet metabolite
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Cowley and Partington, 1936
Cowley, E.G.; Partington, J.R., Studies in dielectric polarisation. Part XV. The dipole moments of fivemembered nitrogen ring compounds: indole,skatole,carbazole,isatin, phthalimide, and succinimide., J. Chem. Soc., 1936, 1936, 47. [all data]

Ribeiro da Silva, Santos, et al., 2006
Ribeiro da Silva, M.A.V.; Santos, C.P.F.; Monte, M.J.S.; Sousa, C.A.D., Thermochemical studies of phthalimide and two N-alkylsubstituted phthalimides (ALKYL=ETHYL AND n-PROPYL), J Therm Anal Calorim, 2006, 83, 3, 533-539, https://doi.org/10.1007/s10973-005-7448-3 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Klochkov, 1956
Klochkov, V.P., Zh. Fiz. Khim., 1956, 30, 2823. [all data]

Cantor, 1978
Cantor, Stanley, Applications of differential scanning calorimetry to the study of thermal energy storage, Thermochimica Acta, 1978, 26, 1-3, 39-47, https://doi.org/10.1016/0040-6031(78)80055-0 . [all data]

Paul and Kebarle, 1989
Paul, G.; Kebarle, P., Electron Affinities of Cyclic Unsaturated Dicarbonyls: Maleic Anhydrides, Maleimides, and Cyclopentendione, J. Am. Chem. Soc., 1989, 111, 2, 464, https://doi.org/10.1021/ja00184a009 . [all data]

Klasinc, Trinajstic, et al., 1980
Klasinc, L.; Trinajstic, N.; Knop, J.V., Application of photoelectron spectroscopy to biologically active molecules and their constituent parts. VIII. Thalidomide, Int. J. Quantum Chem., 1980, 7, 403. [all data]

Galasso, Colonna, et al., 1977
Galasso, V.; Colonna, F.P.; Distefano, G., Photoelectron spectra of 1,2-indandione, 1,3-indandione and heterocyclic analogues, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 227. [all data]

Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R., Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds., Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c . [all data]

Notes

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• Symbols used in this document:
  

  EA	Electron affinity
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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