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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
Deltafgas-89.75 ± 0.36kcal/molCcbYan and Pilcher, 1990Author was aware that data differs from previously reported values; Heat of combustion NR
Deltafgas-86.6 ± 2.2kcal/molCcbSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafsolid-110.00 ± 0.072kcal/molCcbSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol; ALS
Deltafsolid-109.72 ± 0.07kcal/molCcbColeman and Skinner, 1966ALS
Quantity Value Units Method Reference Comment
Deltacsolid-436.989 ± 0.057kcal/molCcbSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol; ALS
Deltacsolid-437.28 ± 0.05kcal/molCcbColeman and Skinner, 1966ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
29.608298.15Steele, Chirico, et al., 1989T = 305 to 495 K. Csat/R(c) = 0.0438T + 1.87 (305 to 355 K); Csat/R(liq) = 0.0265T + 13.38 (405 to 495 K).; DH
31.41323.Satoh and Sogabe, 1941T = 0 to 100°C. Mean value.; DH

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil560.7KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus400.KN/ASorum and Durand, 1952Uncertainty assigned by TRC = 1.5 K; TRC
Tfus398.15KN/ACowley and Partington, 1936Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Deltasub20.0 ± 0.36kcal/molN/AMeng-Yan and Pilcher, 1990AC
Deltasub20.0 ± 0.36kcal/molCYan and Pilcher, 1990Author was aware that data differs from previously reported values; Heat of combustion NR; ALS
Deltasub23.4 ± 1.1kcal/molVSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol; ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
16.0431.AStephenson and Malanowski, 1987Based on data from 416. - 561. K.; AC
17.6403.N/AStull, 1947Based on data from 388. - 560. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
388. - 560.74.978112365.906-86.489Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
19.9 ± 0.36329.MEMeng-Yan and Pilcher, 1990Based on data from 317. - 340. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
4.0631400.Steele, Chirico, et al., 1989DH
4.06400.Domalski and Hearing, 1996AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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
Deltar345.4 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar329.7 ± 4.6kcal/molEIAECooper and Compton, 1973gas phase; B
Quantity Value Units Method Reference Comment
Deltar338.0 ± 2.0kcal/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
Deltar-62.22 ± 0.11kcal/molCmHoward and Skinner, 1966solid phase; solvent: Aqueous solution; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -62.55 ± 0.11 kcal/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
Deltar-67.78 ± 0.07kcal/molCmHoward and Skinner, 1966solid phase; solvent: Aqueous solution; ALS

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)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

Coleman and Skinner, 1966
Coleman, D.J.; Skinner, H.A., Heats of combustion of organic compounds of nitrogen. Part 4.- Succinimide, N,N'-bisuccinimide and 2,5,2',5'-tetramethyl-dipyrryl-(1,1'), Trans. Faraday Soc., 1966, 62, 2057-2062. [all data]

Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T., The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (4), Sci., Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 246-251. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Sorum and Durand, 1952
Sorum, C.H.; Durand, E.A., The Melting of Binary Eutectics, J. Am. Chem. Soc., 1952, 74, 1071. [all data]

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]

Meng-Yan and Pilcher, 1990
Meng-Yan, Yang; Pilcher, G., Enthalpies of combustion of succinic anhydride, glutaric anhydride, and glutarimide, The Journal of Chemical Thermodynamics, 1990, 22, 9, 893-898, https://doi.org/10.1016/0021-9614(90)90177-R . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References