2-Norbornanone
- Formula: C7H10O
- Molecular weight: 110.1537
- IUPAC Standard InChI: InChI=1S/C7H10O/c8-7-4-5-1-2-6(7)3-5/h5-6H,1-4H2
- IUPAC Standard InChIKey: KPMKEVXVVHNIEY-UHFFFAOYSA-N
- CAS Registry Number: 497-38-1
- 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: Bicyclo[2.2.1]heptan-2-one; Norbornan-2-one; Norcampher; Norcamphor; Bicyclo(2.2.1)-2-heptanone; Bicyclo[2.2.1]heptane-2-one; (±)-Bicyclo[2.2.1]heptan-2-one; 8,9,10-trinorbornan-2-one
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -40.8 ± 1.2 | kcal/mol | Ccb | Steele, 1978 | Reanalyzed by Cox and Pilcher, 1970, Original value = -40.1 ± 0.8 kcal/mol |
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 | -51.76 ± 0.65 | kcal/mol | Ccb | Steele, 1978 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -948.17 ± 0.65 | kcal/mol | Ccb | Steele, 1978 | Corresponding ΔfHºsolid = -51.76 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -945.8 ± 1.0 | kcal/mol | Ccb | Becker and Roth, 1934 | Reanalyzed by Cox and Pilcher, 1970, Original value = -946.1 kcal/mol; Corresponding ΔfHºsolid = -54.13 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 443.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 12.0 | kcal/mol | GC | van Roon, Parsons, et al., 2002 | AC |
| ΔvapH° | 12.3 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
| ΔvapH° | 11.9 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 11.7 ± 0.4 | kcal/mol | V | Steele, 1978 | ALS |
| ΔsubH° | 11.7 ± 0.41 | kcal/mol | BG | Steele, 1978 | Based on data from 300. to 340. K.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 0.810 | 368.7 | Acree, 1993 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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
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
+ 2
=
+ 2
By formula: C9H14O2 + 2H2O = C7H10O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 5.491 ± 0.026 | kcal/mol | Cm | Wiberg and Cunningham, 1990 | liquid phase; Heat of hydrolysis |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, 1978
Steele, W.V.,
The standard enthalpies of formation of bicyclic compounds. IV. Bicyclo[2.2.1]heptan-2-one and bicyclo[2.2.1]heptan-7-one,
J. Chem. Thermodyn., 1978, 10, 585-590. [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]
Becker and Roth, 1934
Becker, G.; Roth, W.A.,
Verbrennungswarmen einiger cyclischer kohlenwasserstoffe,
Ber., 1934, 67, 627-632. [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]
van Roon, Parsons, et al., 2002
van Roon, André; Parsons, John R.; Govers, Harrie A.J.,
Gas chromatographic determination of vapour pressure and related thermodynamic properties of monoterpenes and biogenically related compounds,
Journal of Chromatography A, 2002, 955, 1, 105-115, https://doi.org/10.1016/S0021-9673(02)00200-5
. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Acree, 1993
Acree, William E.,
Thermodynamic properties of organic compounds,
Thermochimica Acta, 1993, 219, 97-104, https://doi.org/10.1016/0040-6031(93)80486-T
. [all data]
Wiberg and Cunningham, 1990
Wiberg, K.B.; Cunningham, W.C., Jr.,
Thermochemical studies of carbonyl reactions. 4. Enthalpies of hydrolysis of norbornyl ketals,
J. Org. Chem., 1990, 55, 679-684. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point 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 ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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