Succinimide

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Condensed phase thermochemistry data

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

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

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

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
Δsub20.0 ± 0.36kcal/molN/AMeng-Yan and Pilcher, 1990AC
Δsub20.0 ± 0.36kcal/molCYan and Pilcher, 1990Author was aware that data differs from previously reported values; Heat of combustion NR; ALS
Δsub23.4 ± 1.1kcal/molVSteele, Chirico, et al., 1989Hfusion=12.32 kJ/mol; ALS

Enthalpy of vaporization

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

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

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

Enthalpy of sublimation

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

Enthalpy of fusion

ΔfusH (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

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

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
Δr345.4 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Δr329.7 ± 4.6kcal/molEIAECooper and Compton, 1973gas phase; B
Quantity Value Units Method Reference Comment
Δr338.0 ± 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
Δr-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
Δr-67.78 ± 0.07kcal/molCmHoward and Skinner, 1966solid phase; solvent: Aqueous solution; ALS

Gas phase ion energetics data

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

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
Δr345.4 ± 2.3kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Δr329.7 ± 4.6kcal/molEIAECooper and Compton, 1973gas phase; B
Quantity Value Units Method Reference Comment
Δr338.0 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References, Notes

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, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

UVVis spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

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

Normal alkane RI, polar column, temperature ramp

View large format table.

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, Condensed phase thermochemistry data, Phase change 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]

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]

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References