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2-Norbornanone

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
Deltafgas-40.8 ± 1.2kcal/molCcbSteele, 1978Reanalyzed 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
Deltafsolid-51.76 ± 0.65kcal/molCcbSteele, 1978 
Quantity Value Units Method Reference Comment
Deltacsolid-948.17 ± 0.65kcal/molCcbSteele, 1978Corresponding «DELTA»fsolid = -51.76 kcal/mol (simple calculation by NIST; no Washburn corrections)
Deltacsolid-945.8 ± 1.0kcal/molCcbBecker and Roth, 1934Reanalyzed by Cox and Pilcher, 1970, Original value = -946.1 kcal/mol; Corresponding «DELTA»fsolid = -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
Tboil443.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Deltavap12.0kcal/molGCvan Roon, Parsons, et al., 2002AC
Deltavap12.3kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Deltavap11.9kcal/molCGCChickos, Hosseini, et al., 1995Based on data from 343. - 383. K.; AC
Quantity Value Units Method Reference Comment
Deltasub11.7 ± 0.4kcal/molVSteele, 1978ALS
Deltasub11.7 ± 0.41kcal/molBGSteele, 1978Based on data from 300. - 340. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
0.810368.7Acree, 1993AC

Reaction thermochemistry data

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, 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-Norbornanone dimethyl ketal + 2Water = 2-Norbornanone + 2Methyl Alcohol

By formula: C9H14O2 + 2H2O = C7H10O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar5.491 ± 0.026kcal/molCmWiberg and Cunningham, 1990liquid phase; Heat of hydrolysis

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)202.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity194.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.9PEFrost, Westwood, et al., 1980LLK
9.17 ± 0.02PEFrost, Westwood, et al., 1980Vertical value; LLK
9.14PEHentrich, Gunkel, et al., 1974Vertical value; LLK
8.94 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

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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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 113177

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

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

View large format table.

Column type Active phase I Reference Comment
CapillarySPB-5983.Plettner, Mohle, et al., 200530. m/0.25 mm/0.25 «mu»m; Program: 50C(5min) => 5C/min => 100C(4min) => 50C/min => 250C(20min)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]

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]

Frost, Westwood, et al., 1980
Frost, D.C.; Westwood, N.P.C.; Werstiuk, N.H., Ultraviolet photoelectron spectra of 2-norbornanone, 2,5-norbornanedione. Their akyl derivatives and thio-analogues. An investigation of transannular interactions by photoelectron spectroscopy, Can. J. Chem., 1980, 58, 1659. [all data]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L., Photoelectron spectra of norbornanones and norbornenones, J. Am. Chem. Soc., 1971, 93, 4962. [all data]

Plettner, Mohle, et al., 2005
Plettner, E.; Mohle, A.; Mwangi, M.T.; Griscti, J.; Patrick, B.O.; Nair, R.; Batchelor, R.J.; Einstein, F., 2-Chlorobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2-chlorobicyclo[2.2.1]heptane-2-carboxamide as precursors of bicyclo[2.2.1]hept-5-en-2-one and bicyclo[2.2.1]heptan-2-one: resolution, absolute configuration and hydrogen-bonding properties, Tetrahedron: Asymmetry, 2005, 16, 16, 2754-2763, https://doi.org/10.1016/j.tetasy.2005.07.016 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References