Succinimide

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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-375.5 ± 1.5kJ/molCcbYan and Pilcher, 1990Author was aware that data differs from previously reported values; Heat of combustion NR
Δfgas-362.2 ± 9.3kJ/molCcbSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol

Reaction thermochemistry 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C4H4NO2- + Hydrogen cation = Succinimide

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Δr1445. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1379. ± 19.kJ/molEIAECooper and Compton, 1973gas phase; B
Quantity Value Units Method Reference Comment
Δr1414. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

2,5-Pyrrolidinedione, 1-bromo- + 0.5Hydrazine = Hydrogen bromide + Succinimide + 0.5Nitrogen

By formula: C4H4BrNO2 + 0.5H4N2 = HBr + C4H5NO2 + 0.5N2

Quantity Value Units Method Reference Comment
Δr-260.3 ± 0.46kJ/molCmHoward and Skinner, 1966solid phase; solvent: Aqueous solution; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -261.7 ± 0.46 kJ/mol; ALS

N-Chlorosuccinimide + 0.5Hydrazine = Succinimide + Hydrogen chloride + 0.5Nitrogen

By formula: C4H4ClNO2 + 0.5H4N2 = C4H5NO2 + HCl + 0.5N2

Quantity Value Units Method Reference Comment
Δr-283.6 ± 0.3kJ/molCmHoward and Skinner, 1966solid phase; solvent: Aqueous solution; ALS

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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
10.01PEWorley, Gerson, et al., 1978Vertical value; LLK
10.01PEGerson, Worley, et al., 1978Vertical value; LLK

De-protonation reactions

C4H4NO2- + Hydrogen cation = Succinimide

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Δr1445. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Δr1379. ± 19.kJ/molEIAECooper and Compton, 1973gas phase; B
Quantity Value Units Method Reference Comment
Δr1414. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 421
NIST MS number 228398

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UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Saidel, 1953
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 786
Instrument n.i.g.
Melting point 126.5
Boiling point 287 dec

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

Normal alkane RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryRTX-Wax2458.Prososki, Etzel, et al., 200730. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 10. K/min, 220. C @ 10. min

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Yan and Pilcher, 1990
Yan, Y.M.; Pilcher, G., Enthalpies of combustion of succinic anhydride, glutaric anhydride, and glutarimide, J. Chem. Thermodyn., 1990, 22, 893-898. [all data]

Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of some pure compound ideal-gas enthalpies of formation, AIChE Symp. Ser., 1989, 85, 140-162. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N., Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities, J. Chem. Phys., 1973, 59, 3550. [all data]

Howard and Skinner, 1966
Howard, P.B.; Skinner, H.A., Thermochemistry of some reactions of aqueous hydrazine with halogens, hydrogen halides and N-halogenosuccinimides, J. Chem. Soc. A, 1966, 1536-1540. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Worley, Gerson, et al., 1978
Worley, S.D.; Gerson, S.H.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W., On the structure of N-chlorosuccinimide and N-bromosuccinimide. A photoelectron spectroscopic study, J. Chem. Phys., 1978, 68, 1313. [all data]

Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W., The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [all data]

Saidel, 1953
Saidel, L.J., Contribution of the ultra-violet absorption spectrum of asparagine to the problem of its structure, Nature (London), 1953, 172, 955-956. [all data]

Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A., Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder, J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References