N-Methylmaleimide
- Formula: C5H5NO2
- Molecular weight: 111.0987
- IUPAC Standard InChI: InChI=1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3
- IUPAC Standard InChIKey: SEEYREPSKCQBBF-UHFFFAOYSA-N
- CAS Registry Number: 930-88-1
- 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-Pyrrole-2,5-dione, 1-methyl-; Maleimide, N-methyl-; N-Methylmaleinimide
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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 |
|---|---|---|---|---|---|
| ΔfH°gas | -61.19 ± 0.36 | kcal/mol | Ccb | Roux, Jimenez, et al., 1997 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -78.70 ± 0.33 | kcal/mol | Ccb | Roux, Jimenez, et al., 1997 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -562.33 ± 0.31 | kcal/mol | Ccb | Roux, Jimenez, et al., 1997 |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 17.5 ± 0.1 | kcal/mol | V | Roux, Jimenez, et al., 1997 | ALS |
| ΔsubH° | 17.5 ± 0.1 | kcal/mol | N/A | Roux, Jimenez, et al., 1997 | AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 18.0 ± 0.1 | 282. | ME | Roux, Jimenez, et al., 1997 | Based on data from 276. to 289. K.; AC |
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: John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.114 ± 0.087 | IMRE | Paul and Kebarle, 1989 | ΔGea(423 K) = -25.3±1 kcal/mol, ΔS(est) = -1±1 eu |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roux, Jimenez, et al., 1997
Roux, M.V.; Jimenez, P.; Martin-Luengo, M.A.; Davalos, J.Z.; Sun, Z.; Hosmane, R.S.; Liebman, J.F.,
The elusive antiaromaticity of Maleimides and maleic anhydride: Enthalpies of formation of N-methylmaleimide, N-methylsuccinimide, N-Methylphtalimide, and N-benzoyl-N-methylbenzamide,
J. Org. Chem., 1997, 62, 2732-2737. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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