2-Pyrrolidinone
- Formula: C4H7NO
- Molecular weight: 85.1045
- IUPAC Standard InChI: InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
- IUPAC Standard InChIKey: HNJBEVLQSNELDL-UHFFFAOYSA-N
- CAS Registry Number: 616-45-5
- 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: γ-Aminobutyrolactam; α-Pyrrolidinone; α-Pyrrolidone; γ-Aminobutyric lactam; γ-Butyrolactam; Butanoic acid, 4-amino-, lactam; Butyrolactam; Pyrrolidone; 2-Oxopyrrolidine; 2-Pyrol; 2-Pyrrolidone; 4-Aminobutyric acid lactam; Pyrrolidon; LAM; γ-Aminobutyric acid lactam; 2-Tetrahydropyrrolone; Azacyclopentan-2-one; Pyrrolidone-2; Soluphor P; NSC 4593; NSC 8413; Butanoic acid, 4-amino-; 2-Pyrol4-aminobutyric acid lactam; a-Pyrrolidinone; a-Pyrrolidone; g-Aminobutyric acid lactam; g-Aminobutyric lactam; g-Aminobutyrolactam; g-Butyrolactam; Pyrrolidone2-pyrrolidone; Pyrrolidin-2-one
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -47.17 ± 0.73 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 | -63.59 ± 0.10 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -551.721 ± 0.081 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | ALS |
| ΔcH°liquid | -546.90 ± 0.10 | kcal/mol | Ccb | Strepikeev, Skuratov, et al., 1955 | Reanalyzed by Cox and Pilcher, 1970, Original value = -547.1 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 45.34 | cal/mol*K | N/A | Kolesov, Paukov, et al., 1962 | DH |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 32.70 | cal/mol*K | N/A | Kolesov, Paukov, et al., 1959 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 40.54 | 300. | Steele, Chirico, et al., 1989 | DH |
| 40.49 | 300.00 | Kolesov, Paukov, et al., 1962 | T = 60 to 350 K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 32.41 | 290. | Kolesov, Paukov, et al., 1959 | T = 60 to 335 K.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.2 | PE | Andreocci, Devillanova, et al., 1980 | LLK |
| 9.32 ± 0.02 | PI | Potapov, Filyugina, et al., 1968 | RDSH |
| 9.45 | PE | Andreocci, Devillanova, et al., 1980 | Vertical value; LLK |
| 9.53 | PE | Gerson, Worley, et al., 1978 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H3NO+ | 10.7 | C2H4 | PI | Potapov, Filyugina, et al., 1968 | RDSH |
| C4H6NO+ | 9.9 | H | PI | Potapov, Filyugina, et al., 1968 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, 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., 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]
Strepikeev, Skuratov, et al., 1955
Strepikeev, A.A.; Skuratov, S.M.; Kachinskaya, O.N.; Muromova, R.S.; Brikina, E.P.; Shtekhter, S.M.,
About the tension of cycle in lactames,
Dokl. Akad. Nauk SSSR, 1955, 102, 105-108. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Kolesov, Paukov, et al., 1962
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M.,
Free energy change in the polymerization of lactams under standard conditions [low temperature heat capacities of lactams and potassium],
Zhur. Fiz. Khim., 1962, 36, 770-779. [all data]
Kolesov, Paukov, et al., 1959
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M.; Seregin, E.A.,
Standard entropies of certain lactams,
Dokl. Akad. Nauk., 1959, SSSR 128, 130-132. [all data]
Andreocci, Devillanova, et al., 1980
Andreocci, M.V.; Devillanova, F.A.; Furlani, C.; Mattogno, G.; Verani, G.; Zanoni, R.,
Structural characterization of some substituted azolidine molecules: UPS photoelectron spectroscopic studies,
J. Mol. Struct., 1980, 69, 151. [all data]
Potapov, Filyugina, et al., 1968
Potapov, V.K.; Filyugina, A.D.; Shigorin, D.N.; Ozerova, G.A.,
Photoionization of some compounds containing the carbonyl and amino groups,
Dokl. Akad. Nauk SSSR, 1968, 180, 398, In original 352. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°liquid Entropy of liquid at standard conditions S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas 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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