2,5-Pyrrolidinedione, 1-bromo-
- Formula: C4H4BrNO2
- Molecular weight: 177.984
- IUPAC Standard InChI: InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
- IUPAC Standard InChIKey: PCLIMKBDDGJMGD-UHFFFAOYSA-N
- CAS Registry Number: 128-08-5
- 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: Bromosuccinimide; N-Bromosuccinimide; NBS; Succinbromimide; Succinimide, N-bromo-; 1-Bromo-2,5-pyrrolidine-dione; Succinbromide; Succinibromimide; N-Bromsuccinimide; NSC 16
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
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
+ 0.5
=
+
+ 0.5
By formula: C4H4BrNO2 + 0.5H4N2 = HBr + C4H5NO2 + 0.5N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -260.3 ± 0.46 | kJ/mol | Cm | Howard and Skinner, 1966 | solid phase; solvent: Aqueous solution; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -261.7 ± 0.46 kJ/mol |
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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.12 | PE | Worley, Gerson, et al., 1978 | Vertical value |
| 10.12 | PE | Gerson, Worley, et al., 1978 | Vertical value |
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
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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 | Humboldt-Universitat zu Berlin, Department of Chemistry, Analytical Group |
| NIST MS number | 286939 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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.
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]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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