2-Pyrrolidinone, 1-methyl-
- Formula: C5H9NO
- Molecular weight: 99.1311
- IUPAC Standard InChI: InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
- IUPAC Standard InChIKey: SECXISVLQFMRJM-UHFFFAOYSA-N
- CAS Registry Number: 872-50-4
- 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: M-Pyrol; N-Methyl-α-pyrrolidinone; N-Methyl-α-pyrrolidone; N-Methyl-γ-butyrolactam; N-Methyl-2-pyrrolidinone; N-Methyl-2-pyrrolidone; N-Methylpyrrolidinone; N-Methylpyrrolidone; NMP; 1-Methyl-2-Pyrrolidinone; 1-Methyl-2-pyrrolidone; 1-Methyl-5-pyrrolidinone; 1-Methylpyrrolidinone; 2-Pyrrolidone, 1-methyl-; 1-Methylazacyclopentane-2-one; 1-Methylpyrrolidone; N-Methylpyrrolidone-(2); N-Methylpyrrolid-2-one; Methylpyrrolidone; 1-Methylazacyclopentan-2-one; Agsolex 1; N 0131; N-Methyl-gamma-butyrolactam; Micropure ultra; NSC 4594
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Condensed phase thermochemistry data
Go To: Top, Gas phase ion energetics data, 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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -63.51 ± 0.13 | kcal/mol | Ccr | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -714.16 ± 0.11 | kcal/mol | Ccr | Steele, Chirico, et al., 1990 | Author was aware that data differs from previously reported values; ALS |
| ΔcH°liquid | -715.0 ± 0.1 | kcal/mol | Ccb | Kozina and Skuratov, 1959 | ALS |
| ΔcH°liquid | -715.6 | kcal/mol | Ccb | Skuratov, Kozina, et al., 1958 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 98.57 | 298.15 | Steele, Chirico, et al., 1990 | DH |
| 73.57 | 298. | Marchidan and Ciopec, 1978 | T = 298 to 461 K.; DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
View reactions leading to C5H9NO+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 220.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 213.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.17 | PE | Treschanke and Rademacher, 1985 | Vertical value; LBLHLM |
References
Go To: Top, Condensed phase thermochemistry 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.
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of ideal-gas enthalpies of formation for key compounds,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]
Kozina and Skuratov, 1959
Kozina, M.P.; Skuratov, S.M.,
The enthalphy of polymerization of N-substituted lactames,
Dokl. Akad. Nauk SSSR, 1959, 127, 561-563. [all data]
Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D.,
Heats of combustion of cyclic compounds,
Bull. Chem. Thermodyn., 1958, 1, 21. [all data]
Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M.,
Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry,
J. Therm. Anal., 1978, 14, 131-150. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Treschanke and Rademacher, 1985
Treschanke, L.; Rademacher, P.,
Electronic structure and conformational properties of the amide linkage,
J. Mol. Struct., 1985, 122, 47. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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