Caprolactam
- Formula: C6H11NO
- Molecular weight: 113.1576
- IUPAC Standard InChI: InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)
- IUPAC Standard InChIKey: JBKVHLHDHHXQEQ-UHFFFAOYSA-N
- CAS Registry Number: 105-60-2
- 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: 2H-Azepin-2-one, hexahydro-; ε-Caprolactam; ω-Caprolactam; Aminocaproic lactam; Hexahydro-2-azepinone; Hexahydro-2H-azepin-2-one; Hexanoic acid, 6-amino-, cyclic lactam; 2-Azacycloheptanone; 2-Ketohexamethylenimine; 2-Oxohexamethylenimine; 2-Perhydroazepinone; 6-Caprolactam; 6-Hexanelactam; 6-Aminohexanoic acid cyclic lactam; 1,6-Hexolactam; 2-Ketohexamethyleneimine; Caprolattame; Epsylon kaprolaktam; Hexamethylenimine, 2-oxo-; Hexanoic acid, 6-amino-, lactam; Hexanonisoxim; NCI-C50646; 1-Aza-2-cycloheptanone; 2H-Azepin-7-one, hexahydro-; A1030; Akulon; Alkamid; Amilan cm 1001; Amilan cm 1011; Amilan cm 1001C; Amilan cm 1001G; 6-Aminocaproic acid lactam; ATM 2(NYLON); Bonamid; Capran 80; Capran 77C; Caprolon B; Caprolon V; Capron; Capron 8250; Capron 8252; Capron 8253; Capron 8256; Capron 8257; Capron B; Capron GR 8256; Capron GR 8258; Capron PK4; Chemlon; CM 1001; CM 1011; CM 1031; CM 1041; Danamid; Dull 704; Durethan bk; Durethan bk 30S; Durethan bkv 30H; Durethan bkv 55H; Ertalon 6sa; Extrom 6N; Grilon; Hexanolactam; Itamid; Itamid 250; Itamide 25; Itamide 35; Itamide 250; Itamide 350; Itamide 250G; Itamide S; Kaprolit; Kaprolit B; Kaprolon; Kaprolon B; Kapromine; Kapron; Kapron A; Kapron B; Maranyl F 114; Maranyl F 124; Maranyl F 500; Metamid; Miramid H 2; Miramid wm 55; Nylon A1035sf; Nylon cm 1031; Nylon X 1051; Orgamide; Orgamid RMNOCD; 2-Oxohexamethyleneimine; PA 6; PK 4; PKA; Plaskin 8200; Plaskon 201; Plaskon 8201; Plaskon 8205; Plaskon 8207; Plaskon 8252; Plaskon 8202C; Plaskon 8201hs; Plaskon xp 607; Polyamide pk 4; Relon P; Renyl MV; Sipas 60; Spencer 401; Spencer 601; Steelon; Stilon; Stylon; Tarlon X-A; Tarlon XB; Tarnamid T; Tarnamid T 2; Tarnamid T 27; Torayca N 6; UBE 1022B; Ultramid B 3; Ultramid B 4; Ultramid B 5; Ultramid BMK; Vidlon; Widlon; Zytel 211; 6-Aminohexanoic acid lactam; Hexano-6-lactam; Azepan-2-one; 2-Azepanone; 117955-36-9; 2953-03-9; 34876-18-1; 168214-28-6
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction 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 | -239.6 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -329.4 ± 1.7 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3603.8 ± 1.5 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
| ΔcH°solid | -3603.7 ± 0.84 | kJ/mol | Ccb | Strepikeev, Skuratov, et al., 1955 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3605. kJ/mol; ALS |
| ΔcH°solid | -3588. ± 6.3 | kJ/mol | Ccb | Runge and Maass, 1953 | At 293 °K; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 173.21 | J/mol*K | N/A | Kabo, Kozyro, et al., 1992, 2 | DH |
| S°solid,1 bar | 168.4 | J/mol*K | N/A | Kolesov, Paukov, et al., 1962 | DH |
| S°solid,1 bar | 168.6 | J/mol*K | N/A | Kolesov, Paukov, et al., 1959 | DH |
| S°solid,1 bar | 168.6 | J/mol*K | N/A | Paukov, Kolesov, et al., 1959 | Debye-Einstein extrapolation below 60 K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 156.78 | 298.15 | Kabo, Kozyro, et al., 1992, 2 | T = 5 to 550 K. Cp(liq) = 323.08 + 0.0342(T/K) - 1.1074x10-7(T/K)2 J/mol*K (340 to 520 K).; DH |
| 156.3 | 300.00 | Kolesov, Paukov, et al., 1962 | T = 60 to 350 K.; DH |
| 158.1 | 300. | Kolesov, Paukov, et al., 1959 | T = 60 to 370 K.; DH |
| 156.77 | 298.15 | Paukov, Kolesov, et al., 1959 | T = 60 to 373 K.; DH |
Reaction 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
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
=
By formula: C6H11NO = C6H11NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -105.1 ± 4.2 | kJ/mol | Ciso | Kozyro, Marachuk, et al., 1989 | solid phase |
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C6H11NO+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.07 ± 0.02 | PI | Potapov, Filyugina, et al., 1968 | RDSH |
| 9.19 | PE | Treschanke and Rademacher, 1985 | Vertical value; LBLHLM |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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.
Kabo, Kozyro, et al., 1992
Kabo, G.J.; Kozyro, A.A.; Krouk, V.S.; Sevruk, V.M.; Yursha, I.A.; Simirsky, V.V.; Gogolinsky, V.I.,
Thermodynamic properties of 6-aminohexanoic lactam (ε-caprolactam),
J. Chem. Thermodyn., 1992, 24, 1-3. [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]
Runge and Maass, 1953
Runge, F.; Maass, P.,
Untersuchungen uber die Beckmann=Umlagerung des Zyklohexanonoxims,
Chem. Tech. (Berlin), 1953, 5, 421-424. [all data]
Kabo, Kozyro, et al., 1992, 2
Kabo, G.J.; Kozyro, A.A.; Krouk, V.S.; Sevruk, V.M.; Yursha, I.A.; Simirsky, V.V.; Gogolinsky, V.I.,
Thermodynamic properties of 6-aminohexanoic lactam (e-caprolactam),
J. Chem. Thermodynam., 1992, 24, 1-13. [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]
Paukov, Kolesov, et al., 1959
Paukov, I.E.; Kolesov, V.P.; Skuratov, S.M.,
Determination of isobaric-isothermal potential at standard conditions for the polymerization reaction of e-caprolactam,
Doklady Akad. Nauk, 1959, SSSR 126, 325-326. [all data]
Kozyro, Marachuk, et al., 1989
Kozyro, A.A.; Marachuk, L.I.; Krasulin, A.P.; Yursha, I.A.; Kabo, G.Ya.,
Thermodynamic properties of cyclohexanone oxime and ε-caprolactam,
J. Appl. Chem. USSR, 1989, 62, 547-550. [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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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