1,1'-Bicyclohexyl

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-52.19 ± 0.74kcal/molCcbMontgomery, Rossini, et al., 1978ALS
Δfgas-51.46kcal/molN/AGood and Lee, 1976Value computed using ΔfHliquid° value of -273.3±1.2 kj/mol from Good and Lee, 1976 and ΔvapH° value of 58.0 kj/mol from Montgomery, Rossini, et al., 1978.; DRB

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
Δfliquid-66.05 ± 0.74kcal/molCcbMontgomery, Rossini, et al., 1978ALS
Δfliquid-65.32 ± 0.29kcal/molCcbGood and Lee, 1976ALS
Quantity Value Units Method Reference Comment
Δcliquid-1814.03 ± 0.63kcal/molCcbMontgomery, Rossini, et al., 1978Corresponding Δfliquid = -66.05 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1814.76 ± 0.24kcal/molCcbGood and Lee, 1976Corresponding Δfliquid = -65.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1778.12kcal/molCcbGollis, Belenyessy, et al., 1962Corresponding Δfliquid = -101.96 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1815.6kcal/molCcbWise, Serijan, et al., 1951Corresponding Δfliquid = -64.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1801.5 ± 1.5kcal/molCcbBrull, 1935Reanalyzed by Cox and Pilcher, 1970, Original value = -1799.35 kcal/mol; Corresponding Δfliquid = -78.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
67.64298.15O'Rourke and Mraw, 1983T = 220 to 475 K. Cp = 0.7589 (T/K) + 56.7 (277.2 to 475 K) J/mol*K.; DH
71.7313.Gudinowicz, Campbell, et al., 1963T = 313 to 483 K.; DH
71.80311.Gollis, Belenyessy, et al., 1962, 2Temperatures 100, 200, 300°F.; DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil508. ± 10.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus276.9 ± 0.4KAVGN/AAverage of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple276.9KN/APilcher, 1957Uncertainty assigned by TRC = 0.002 K; TRC
Quantity Value Units Method Reference Comment
Δvap13.86kcal/molN/AMajer and Svoboda, 1985 
Δvap13.86 ± 0.06kcal/molCMontgomery, Rossini, et al., 1978ALS
Δvap13.9kcal/molN/AMontgomery, Rossini, et al., 1978DRB
Δvap13.9 ± 0.05kcal/molCMontgomery, Rossini, et al., 1978AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
372. to 373.0.01Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.9346.AStephenson and Malanowski, 1987Based on data from 331. to 511. K.; AC
12.0435.N/AWieczorek and Kobayashi, 1981AC
10.2525.N/AWieczorek and Kobayashi, 1981AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
1.64276.8ACChirico, Cowell, et al., 1998Based on data from 6. to 440. K.; AC
1.62277.2DSCDomalski and Hearing, 1996See also O'Rourke and Mraw, 1983.; AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
1.44256.1Domalski and Hearing, 1996CAL
0.662267.5
6.188273.5
5.846277.2

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.3227256.5crystaline, IVcrystaline, IIIHorn, Klaeboe, et al., 1992DH
0.0765267.0crystaline, IIIcrystaline, IIHorn, Klaeboe, et al., 1992DH
1.695273.6crystaline, IIcrystaline, IHorn, Klaeboe, et al., 1992DH
1.580277.4crystaline, IliquidHorn, Klaeboe, et al., 1992Crystal/isotropic liquid transition.; DH
0.3681256.1crystaline, IVcrystaline, IIIO'Rourke and Mraw, 1983DH
0.177267.5crystaline, IIIcrystaline, IIO'Rourke and Mraw, 1983DH
1.692273.5crystaline, IIcrystaline, IO'Rourke and Mraw, 1983DH
1.620277.2crystaline, IliquidO'Rourke and Mraw, 1983DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.3256.5crystaline, IVcrystaline, IIIHorn, Klaeboe, et al., 1992DH
0.29267.0crystaline, IIIcrystaline, IIHorn, Klaeboe, et al., 1992DH
6.19273.6crystaline, IIcrystaline, IHorn, Klaeboe, et al., 1992DH
5.69277.4crystaline, IliquidHorn, Klaeboe, et al., 1992Crystal/isotropic; DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

(Z) 3,3'-Bis-(1-cyclohexenylidene) + 3Hydrogen = 1,1'-Bicyclohexyl

By formula: C12H16 + 3H2 = C12H22

Quantity Value Units Method Reference Comment
Δr-73.7 ± 0.2kcal/molChydRoth, Adamczak, et al., 1991liquid phase

(E) 3,3'-Bis-(1-cyclohexenylidene) + 3Hydrogen = 1,1'-Bicyclohexyl

By formula: C12H16 + 3H2 = C12H22

Quantity Value Units Method Reference Comment
Δr-73.4 ± 0.2kcal/molChydRoth, Adamczak, et al., 1991liquid phase

2Hydrogen + Bi-2-cyclohexen-1-yl = 1,1'-Bicyclohexyl

By formula: 2H2 + C12H18 = C12H22

Quantity Value Units Method Reference Comment
Δr-57.4 ± 0.2kcal/molChydRoth, Adamczak, et al., 1991liquid phase

3Hydrogen + Benzene, cyclohexyl- = 1,1'-Bicyclohexyl

By formula: 3H2 + C12H16 = C12H22

Quantity Value Units Method Reference Comment
Δr-54.kcal/molEqkFrye, 1962liquid 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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference
9.41PEBodor, Dewar, et al., 1970

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

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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 Japan AIST/NIMC Database- Spectrum MS-NW-2803
NIST MS number 231643

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

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30130.1313.Bredael, 1982Column length: 100. m; Column diameter: 0.5 mm
PackedSE-30150.1324.Shlyakhov, Anvaer, et al., 1975 
CapillarySqualane100.1309.Mitra, Mohan, et al., 1974H2; Column length: 50. m; Column diameter: 0.2 mm
CapillarySqualane100.1295.Besson and Gäumann, 1973Column length: 50. m; Column diameter: 0.25 mm
CapillaryApiezon L100.1327.Besson and Gäumann, 1973Column length: 50. m; Column diameter: 0.25 mm
PackedSE-30130.1284.Antheaume and Guiochon, 1965 
PackedSE-30170.1327.Antheaume and Guiochon, 1965 
PackedMethyl Silicone130.1284.Antheaume and Guiochon, 1965 

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-51301.5Song, Lai, et al., 200330. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51301.2Song, Lai, et al., 200330. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C
CapillaryDB-51293.1Song, Lai, et al., 200330. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51301.5Song, Lai, et al., 200330. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51307.8Song, Lai, et al., 200330. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C
CapillaryUltra-11304.39Richmond and Pombo-Villar, 199725. m/0.32 mm/0.52 μm, 15. K/min, 320. C @ 10. min; Tstart: 35. C
CapillaryDB-51293.1Lai and Song, 199530. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51301.5Lai and Song, 199530. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51307.8Lai and Song, 199530. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51301.5Lai and Song, 199530. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C
CapillaryDB-51301.2Lai and Song, 199530. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C

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

View large format table.

Column type Active phase I Reference Comment
PackedSE-301312.Peng, Ding, et al., 1988Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min)

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-51298.Woerdenbag, Windono, et al., 200430. m/0.249 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 300. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.1313.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1420.Peng, Yang, et al., 1991Program: not specified
CapillaryDB-Wax1431.Peng, Yang, et al., 1991Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.

Montgomery, Rossini, et al., 1978
Montgomery, R.L.; Rossini, F.D.; Mansson, M., Enthalpies of combustion, vaporization, and formation of phenylbenzene, cyclohexylbenzene, and cyclohexylcyclohexane; enthalpy of hydrogenation of certain aromatic systems, J. Chem. Eng. Data, 1978, 23, 125-129. [all data]

Good and Lee, 1976
Good, W.D.; Lee, S.H., The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons, J. Chem. Thermodyn., 1976, 8, 643-650. [all data]

Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J., Evaluation of pure hydrocarbons as jet fuels, J. Chem. Eng. Data, 1962, 7, 331-316. [all data]

Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A., NACA Technical Report 1003, NACA Technical Report 1003, 1951, 1-10. [all data]

Brull, 1935
Brull, L., Sui calori di combustione di alcuni derivati del bifenil, Gazz. Chim. Ital., 1935, 65, 19-28. [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]

O'Rourke and Mraw, 1983
O'Rourke, D.F.; Mraw, S.C., Heat capacities and enthalpies of fusion of dibenzothiophene (220 to 560 K) and of biphenyl, cyclohexylbenzene, and cyclohexylcyclohexane (220 to 475 K). Enthalpies and temperatures of three transitions in solid cyclohexylcyclohexane, J. Chem. Thermodynam., 1983, 15, 489-502. [all data]

Gudinowicz, Campbell, et al., 1963
Gudinowicz, B.J.; Campbell, R.H.; Adams, J.S., Specific heat measurements of complex saturated hydrocarbons, J. Chem. Eng. Data, 1963, 8, 201-214. [all data]

Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J., Evaluations of pure hydrocarbons as Jet Fuels, J. Chem. Eng. Data, 1962, 7, 311-316. [all data]

Pilcher, 1957
Pilcher, G., Anal. Chim. Acta, 1957, 17, 144. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 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]

Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki, Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures, J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005 . [all data]

Chirico, Cowell, et al., 1998
Chirico, R.D.; Cowell, A.B.; Good, W.D.; Klots, T.D.; Knipmeyer, S.E.; Nguyen, A.; Rau, A.P.; Reynolds, J.W.; Smith, N.K.; Steele, W.V., Heat capacities, enthalpy increments, phase transitions, and derived thermodynamic functions for the condensed phases of bicyclohexyl between the temperatures 6 K and 440 K, The Journal of Chemical Thermodynamics, 1998, 30, 12, 1423-1439, https://doi.org/10.1006/jcht.1998.0399 . [all data]

Domalski and Hearing, 1996
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]

Horn, Klaeboe, et al., 1992
Horn, A.; Klaeboe, P.; Nielsen, C.; Mastryukov, V.S.; Myrvold, B.O.; Redford, K., Solid phases of bicyclohexyl studied with vibrational spectroscopy and calorimetry, 1992, Analyst(London) 117(3)355-360. [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Frye, 1962
Frye, C.G., Equilibria in the hydrogenation of polycyclic aromatics, J. Chem. Eng. Data, 1962, 7, 592-595. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method, J. Am. Chem. Soc., 1970, 92, 19. [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I., On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices, Zh. Anal. Khim., 1975, 30, 788-792. [all data]

Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A., Gas chromatographic analysis of complex hydrocarbon mixtures, J. Chromatogr. A, 1974, 91, 633-648, https://doi.org/10.1016/S0021-9673(01)97944-0 . [all data]

Besson and Gäumann, 1973
Besson, R.; Gäumann, T., Indices de rétention de cycloalcanes, cycloalcènes, bicycloalkyles, cycloalkyl-cycloalcényles et bicycloalcényles en chromatographie en phase gazeuse, Helv. Chim. Acta, 1973, 56, 3, 1159-1164, https://doi.org/10.1002/hlca.19730560339 . [all data]

Antheaume and Guiochon, 1965
Antheaume, J.; Guiochon, G., Application de la chromatographie en phase gazeuse à l'étude de la composition des fractions moyennes d'un brut pétrolier, Bull. Soc. Chim. Fr., 1965, 2, 298-307. [all data]

Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B., Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]

Richmond and Pombo-Villar, 1997
Richmond, R.; Pombo-Villar, E., Short communication. Gas chromatography-mass spectrometry coupled with pseudo-Sadtler retention indices, for the identification of components in the essential oil of Curcuma longa L., J. Chromatogr. A, 1997, 760, 2, 303-308, https://doi.org/10.1016/S0021-9673(96)00802-3 . [all data]

Lai and Song, 1995
Lai, W.-C.; Song, C., Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels, Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Woerdenbag, Windono, et al., 2004
Woerdenbag, H.J.; Windono, T.; Bos, R.; Riswan, S.; Quax, W.J., Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia, Flavour Fragr. J., 2004, 19, 2, 145-148, https://doi.org/10.1002/ffj.1284 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [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, Mass spectrum (electron ionization), Gas Chromatography, References