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) Copy

  
• IUPAC Standard InChIKey: HNJBEVLQSNELDL-UHFFFAOYSA-N Copy
• 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
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• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Constant pressure heat capacity of solid

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:
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

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

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 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

Appearance energy determinations

IR Spectrum

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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

Gas Phase Spectrum

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Additional Data

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

Gas Chromatography

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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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

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), Gas Chromatography, NIST Free Links, 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]

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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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Blumenshine and Sears, 1966
Blumenshine, R.L.; Sears, P.G., Several Properties of the 2-Pyrrolidone-Water System as Functions of Composition and Temperature, J. Chem. Eng. Data, 1966, 11, 141. [all data]

Strepikheev, Skuratov, et al., 1955
Strepikheev, A.A.; Skuratov, S.M.; Kachinskaya, O.N.; Muromova, R.S.; Brykina, E.P.; Shtekher, S.M., Dokl. Akad. Nauk SSSR, 1955, 102, 105. [all data]

Kolesov, Paukov, et al., 1962, 2
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M., Free energy change in the polymerizations of lactams under standard conditions chloride), Zh. Fiz. Khim., 1962, 36, 770. [all data]

Morgan and Kopp, 1998
Morgan, Kathleen M.; Kopp, Daniel A., Solvent effects on the stability of simple secondary amides «8224», J. Chem. Soc., Perkin Trans. 2, 1998, 12, 2759-2764, https://doi.org/10.1039/a802717j . [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

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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]

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]

Dallüge, van Stee, et al., 2002
Dallüge, J.; van Stee, L.L.P.; Xu, X.; Williams, J.; Beens, J.; Vreuls, R.J.J.; Brinkman, U.A.Th., Unravelling the composition of very complex samples by comprehensive gas chromatography coupled to time-of-flight mass spectrometry. Cigarette smoke, J. Chromatogr. A, 2002, 974, 1-2, 169-184, https://doi.org/10.1016/S0021-9673(02)01384-5 . [all data]

Kim, Shin, et al., 2001
Kim, T.H.; Shin, J.H.; Baek, H.H.; Lee, H.J., Volatile flavour compounds in suspension culture of Agastache rugosa Kuntze (Korean mint), J. Sci. Food Agric., 2001, 81, 6, 569-575, https://doi.org/10.1002/jsfa.845 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Chung, Fung, et al., 2005
Chung, H.Y.; Fung, P.K.; Kim, J.-S., Aroma impact components in commercial plain sufu, J. Agric. Food Chem., 2005, 53, 5, 1684-1691, https://doi.org/10.1021/jf048617d . [all data]

Aubert, Günata, et al., 2003
Aubert, C.; Günata; Ambid, C.; Baumes, R., Changes in physicochemical characteristics and volatile constituents of yellow- and white-fleshed nectarines during maturation and artificial ripening, J. Agric. Food Chem., 2003, 51, 10, 3083-3091, https://doi.org/10.1021/jf026153i . [all data]

Vasta, Ratel, et al., 2007
Vasta, V.; Ratel, J.; Engel, E., Mass Spectrometry Analysis of Volatile Compounds in Raw Meat for the Authentication of the Feeding Background of Farm Animals, J. Agric. Food Chem., 2007, 55, 12, 4630-4639, https://doi.org/10.1021/jf063432n . [all data]

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Chen, J.; Ho, C.-T., Comparison of volatile generation in serine/threonine/glutamine-ribose/glucose/fructose model systems, J. Agric. Food Chem., 1999, 47, 2, 643-647, https://doi.org/10.1021/jf980771a . [all data]

Machiels, van Ruth, et al., 2003
Machiels, D.; van Ruth, S.M.; Posthumus, M.A.; Istasse, L., Gas chromatography-olfactometry analysis of the volatile compounds of two commercial Irish beef meats, Talanta, 2003, 60, 4, 755-764, https://doi.org/10.1016/S0039-9140(03)00133-4 . [all data]

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Buchbauer, G.; Nikiforov, A.; Remberg, B., Headspace constituents of opium, Planta Medica, 1994, 60, 2, 181-183, https://doi.org/10.1055/s-2006-959447 . [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]

Wei, Mura, et al., 2001
Wei, A.; Mura, K.; Shibamoto, T., Antioxidative activity of volatile chemicals extracted from beer, J. Agric. Food Chem., 2001, 49, 8, 4097-4101, https://doi.org/10.1021/jf010325e . [all data]

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Welke, J.E.; Manfroi, V.; Zanus, M.; Lazarotto, M.; Zini, C.A., Characterization of the volatile profile of Brazilian merlot wines through comprehensive two dimensional gas chromatography time-of-flight mass spectrometric detection, J. Chromatogr. A, 2012, 1226, 124-139, https://doi.org/10.1016/j.chroma.2012.01.002 . [all data]

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Krings, U.; Zelena, K.; Wu, S.; Berger, R.G., Thin-layer high-vacuum distillation to isolate volatile flavour compounds of cocoa powder, Eur. Food Res. Technol., 2006, 223, 5, 675-681, https://doi.org/10.1007/s00217-006-0252-x . [all data]

Notes

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), Gas Chromatography, NIST Free Links, 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)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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