Benzophenone

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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

Quantity Value Units Method Reference Comment
Δfgas49.9 ± 3.0kJ/molCmSabbah and Laffitte, 1978 

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
Δfsolid-34.kJ/molCcbColomina, Cambeiro, et al., 1959ALS
Δfsolid-33.kJ/molCcbSpringall and White, 1954ALS
Δfsolid-32.3 ± 3.3kJ/molCcbParks, Mosley, et al., 1950Reanalyzed by Cox and Pilcher, 1970, Original value = -32.9 ± 0.02 kJ/mol; ALS
Δfsolid-50.84kJ/molCcbLandrieu and Blatt, 1924ALS
Quantity Value Units Method Reference Comment
Δcsolid-6508. ± 10.kJ/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
224.80300.DeKruif, Van Miltenburg, et al., 1983T = 80 to 345 K.; 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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil550. ± 100.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus321.2 ± 0.7KAVGN/AAverage of 23 out of 24 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple321.03KN/ADe Kruif, van Miltenburg, et al., 1983Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc830.KN/ASteele, Chirico, et al., 1994Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Pc33.52barN/ASteele, Chirico, et al., 1994Uncertainty assigned by TRC = 0.04 bar; TRC
Quantity Value Units Method Reference Comment
ρc1.762mol/lN/ASteele, Chirico, et al., 1994Uncertainty assigned by TRC = 0.02 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap94.977kJ/molVNeumann and Volker, 1932ALS
Quantity Value Units Method Reference Comment
Δsub89. ± 10.kJ/molAVGN/AAverage of 11 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
497. to 497.0.133Buckingham and Donaghy, 1982BS
430.70.013Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
59.0545.N/AJaquerod and Wassmer, 2006Based on data from 530. to 575. K. See also Boublik, Fried, et al., 1984.; AC
65.1448.AStephenson and Malanowski, 1987Based on data from 433. to 673. K.; AC
62.2488.N/ADreisbach and Shrader, 1949Based on data from 473. to 579. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
473.7 to 579.34.362382116.372-93.43Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
92.9 ± 0.8306.MEGinkel, Kruif, et al., 2001Based on data from 294. to 318. K.; AC
89.96308.MEStephenson and Malanowski, 1987Based on data from 298. to 318. K. See also Pribilová and Pouchlý, 1974.; AC
95. ± 1.321.DMKruif, Miltenburg, et al., 1983AC
95.0 ± 0.2304.MEColomina, Jimenez, et al., 1980Based on data from 295. to 313. K.; AC
93.9 ± 0.5307.TE,MEDe Kruif and Van Ginkel, 1977Based on data from 297. to 317. K.; AC
95.0 ± 1.5305.TEDeKruif, van Ginkel, et al., 1975Based on data from 293. to 318. K.; AC
96.1306.N/ASerpinskii, Voitkevich, et al., 1956Based on data from 293. to 319. K.; AC
78.2 ± 1.2303.N/AWolf and Weghofer, 1938Based on data from 290. to 315. K. See also Wolf and Trieschmann, 1934.; AC
78.2 ± 0.8313.VWolf and Weghofer, 1938, 2ALS

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
18.194321.03N/ADeKruif, Van Miltenburg, et al., 1983DH
18.81321.2ACChirico, Knipmeyer, et al., 2002Based on data from 5. to 440. K.; AC
18.47321.3ACHanaya, Hikima, et al., 2002AC
18.19324.2N/ADomalski and Hearing, 1996AC
17.669321.2N/AEykman, 1889DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
56.67321.03DeKruif, Van Miltenburg, et al., 1983DH
55.0321.2Eykman, 1889DH

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: José A. Martinho Simões

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

C13H10NaO (solution) + 0.5Dicobalt octacarbonyl (solution) = C4CoNaO4 (solution) + Benzophenone (solution)

By formula: C13H10NaO (solution) + 0.5C8Co2O8 (solution) = C4CoNaO4 (solution) + C13H10O (solution)

Quantity Value Units Method Reference Comment
Δr-157. ± 11.kJ/molRSCKiss, Nolan, et al., 1994solvent: Tetrahydrofuran

Benzophenone (solution) + sodium (cr) = C13H10NaO (solution)

By formula: C13H10O (solution) + Na (cr) = C13H10NaO (solution)

Quantity Value Units Method Reference Comment
Δr-161.1 ± 2.5kJ/molRSCKiss, Nolan, et al., 1994solvent: Tetrahydrofuran

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
L - Sharon G. Lias

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
B - John E. Bartmess

View reactions leading to C13H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.08 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)882.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity852.5kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.62 ± 0.10IMREGrimsrud, Caldwell, et al., 1985ΔGea(423 K) = -15.3 kcal/mol; ΔSea (estimated) = +2.0 eu; B
1.110 ± 0.040LPESMaeyama, Yagi, et al., 2008Stated EA is Vertical Detachment Energy. Threshold adiabatic EA appears to be ca. 0.6 eV - JEB; B
0.655 ± 0.087IMREHuh, Kang, et al., 1999ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B
0.694 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -16.7 kcal/mol; ΔSea = 2.0, est. from data in Kebarle and Chowdhury, 1987; B
0.642 ± 0.052ECDChen and Wentworth, 1983B

Ionization energy determinations

IE (eV) Method Reference Comment
9.4 ± 0.1EIGrutzmacher and Schubert, 1979LLK
9.28EIElder, Beynon, et al., 1976LLK
9.5 ± 0.1EIKrenmayr, Heller, et al., 1974LLK
9.5 ± 0.1EIHeller, Varmuza, et al., 1974LLK
9.46EIBenoit, 1973LLK
9.14 ± 0.03PIIskakov and Potapov, 1971LLK
9.46 ± 0.05EINatalis and Franklin, 1965RDSH
9.35 ± 0.04EIFoffani, Pignataro, et al., 1964RDSH
9.4PITerenin, 1961RDSH
9.05 ± 0.05PEMcAlduff and Bunbury, 1979Vertical value; LLK
9.05PECentineo, Fragala, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+15.67C6H5+COEIBenoit, 1973LLK
C6H5+16.22 ± 0.07?EINatalis and Franklin, 1965RDSH
C7H5O+12.0 ± 0.1C6H5EIGrutzmacher and Schubert, 1979LLK
C7H5O+11.45C6H5EIElder, Beynon, et al., 1976LLK
C7H5O+11.4 ± 0.1C6H5EIHeller, Varmuza, et al., 1974LLK
C7H5O+11.72C6H5EIBenoit, 1973LLK
C7H5O+12.00 ± 0.05C6H5EINatalis and Franklin, 1965RDSH
C12H8+17.48 ± 0.12?EINatalis and Franklin, 1965RDSH
C12H9+15.28 ± 0.05CO+H?EINatalis and Franklin, 1965RDSH
C12H10+12.24 ± 0.13COEINatalis and Franklin, 1965RDSH

References

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

Sabbah and Laffitte, 1978
Sabbah, R.; Laffitte, M., Etude thermodynamique de la molecule de benzophenone, Thermochim. Acta, 1978, 23, 196-198. [all data]

Colomina, Cambeiro, et al., 1959
Colomina, M.; Cambeiro, M.; Perez-Ossorio, R.; Latorre, C., Estudios acerca de calores de combustion II. Calores de combustion de benzofenona y sus p-alquilderivados, Ber. Bunsenges. Phys. Chem., 1959, 509-514. [all data]

Springall and White, 1954
Springall, H.D.; White, T.R., Heats of combustion and molecular structure. Part II. The mean bond energy term for the carbonyl system in certain ketones, J. Chem. Soc., 1954, 2765-27. [all data]

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [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]

Landrieu and Blatt, 1924
Landrieu, P.; Blatt, H., Thermochemical study of diphenylphenylethinylcarbinol and its derivatives, Bull. Soc. Chim. Fr., 1924, 35, 1424-1236. [all data]

DeKruif, Van Miltenburg, et al., 1983
DeKruif, C.G.; Van Miltenburg, J.C.; Blok, J.G., Molar heat capacities and vapour pressures of solid and liquid benzophenone, J. Chem. Thermodynam., 1983, 15, 129-136. [all data]

De Kruif, van Miltenburg, et al., 1983
De Kruif, C.G.; van Miltenburg, J.C.; Blok, J.G., Molar heat capacities and vapour pressures of solid and liquid benzophenone, J. Chem. Thermodyn., 1983, 15, 129. [all data]

Steele, Chirico, et al., 1994
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., DIPPR project 871. Determination of ideal-gas enthalpies of formation for key compounds. The 1990 project results, Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Ser. No. 2, p. 188-215. [all data]

Neumann and Volker, 1932
Neumann, K.; Volker, E., Eine drehwaagemethode zur messung kleinster dampfdruck, Z. Phys. Chem., 1932, 161, 33-45. [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]

Jaquerod and Wassmer, 2006
Jaquerod, Adrien; Wassmer, Eugene, Ueber den Siedepunkt des Naphtalins, des Diphenyls und des Benzophenons unter verschiedenem Druck und dessen Bestimmung mit Hilfe des Wasserstoffthermometers, Ber. Dtsch. Chem. Ges., 2006, 37, 3, 2531-2534, https://doi.org/10.1002/cber.19040370303 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053 . [all data]

Ginkel, Kruif, et al., 2001
Ginkel, C.H.D. van; Kruif, C.G. de; Waal, F.E.B. de, The need for temperature control in effusion experiments (and application to heat of sublimation determination), J. Phys. E: Sci. Instrum., 2001, 8, 6, 490-492, https://doi.org/10.1088/0022-3735/8/6/018 . [all data]

Pribilová and Pouchlý, 1974
Pribilová, J.; Pouchlý, J., Vapour pressure of some low-volatile hydrocarbons determined by the effusion method, Collect. Czech. Chem. Commun., 1974, 39, 5, 1118-1124, https://doi.org/10.1135/cccc19741118 . [all data]

Kruif, Miltenburg, et al., 1983
Kruif, C.G. de; Miltenburg, J.C. van; Blok, J.G., Molar heat capacities and vapour pressures of solid and liquid benzophenone, The Journal of Chemical Thermodynamics, 1983, 15, 2, 129-136, https://doi.org/10.1016/0021-9614(83)90151-9 . [all data]

Colomina, Jimenez, et al., 1980
Colomina, M.; Jimenez, P.; Turrion, C.; Fernandez, J.A.; Monzon, C., An. Quim. Ser. A, 1980, 76, 245. [all data]

De Kruif and Van Ginkel, 1977
De Kruif, C.G.; Van Ginkel, C.H.D., Torsion-weighing effusion vapour-pressure measurements on organic compounds, The Journal of Chemical Thermodynamics, 1977, 9, 8, 725-730, https://doi.org/10.1016/0021-9614(77)90015-5 . [all data]

DeKruif, van Ginkel, et al., 1975
DeKruif, C.G.; van Ginkel, C.H.D.; Voogd, J., Torsion-effusion vapour pressure measurements of organic compounds, Conf. Int. Thermodyn. Chim. C. R. 4th, 1975, 8, 11-18. [all data]

Serpinskii, Voitkevich, et al., 1956
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y., Zh. Fiz. Khim., 1956, 30, 177. [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z., Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]

Wolf and Trieschmann, 1934
Wolf, K.L.; Trieschmann, H.G., Z. Phys. Chem. Abt. B, 1934, 27, 376. [all data]

Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Chirico, Knipmeyer, et al., 2002
Chirico, R.D.; Knipmeyer, S.E.; Steele, W.V., Heat capacities, enthalpy increments, and derived thermodynamic functions for benzophenone between the temperatures 5K and 440K, The Journal of Chemical Thermodynamics, 2002, 34, 11, 1885-1895, https://doi.org/10.1016/S0021-9614(02)00261-6 . [all data]

Hanaya, Hikima, et al., 2002
Hanaya, Minoru; Hikima, Takaaki; Hatase, Minoru; Oguni, Masaharu, Low-temperature adiabatic calorimetry of salol and benzophenone and microscopic observation of their crystallization: finding of homogeneous-nucleation-based crystallization, The Journal of Chemical Thermodynamics, 2002, 34, 8, 1173-1193, https://doi.org/10.1006/jcht.2002.0976 . [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]

Eykman, 1889
Eykman, J.F., Zur kryoskopischen Molekulargewichtsbestimmung, Z. Physik. Chem., 1889, 4, 497-519. [all data]

Kiss, Nolan, et al., 1994
Kiss, G.; Nolan, S.P.; Hoff, C.D., Inorg. Chim. Acta, 1994, 227, 285. [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]

Grimsrud, Caldwell, et al., 1985
Grimsrud, E.; Caldwell, G.; Kebarle, P., Electron affinities from electron transfer equilibria: A- + B = A + B-, J. Am. Chem. Soc., 1985, 107, 4627. [all data]

Maeyama, Yagi, et al., 2008
Maeyama, T.; Yagi, I.; Fujii, A.; Mikami, N., Photoelectron spectroscopy of microsolvated benzophenone radical anions to reveal the origin of solvatochromic shifts in alcoholic media, Chem. Phys. Lett., 2008, 457, 1-3, 18-22, https://doi.org/10.1016/j.cplett.2008.03.055 . [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Chen and Wentworth, 1983
Chen, E.C.M.; Wentworth, W.E., Determination of molecular electron affinities using the electron capture detector in the pulse sampling mode at steady state, J. Phys. Chem., 1983, 87, 45. [all data]

Grutzmacher and Schubert, 1979
Grutzmacher, H.-F.; Schubert, R., Substituent effects in the mass spectra of benzoyl hetarenes, Org. Mass Spectrom., 1979, 14, 567. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Krenmayr, Heller, et al., 1974
Krenmayr, P.; Heller, R.; Varmuza, K., Massenspektrometrische untersuchungen an benzophenon und substituierten benzophenonen. I. Ermittlung thermodynamischer grossen, Org. Mass Spectrom., 1974, 9, 998. [all data]

Heller, Varmuza, et al., 1974
Heller, R.; Varmuza, K.; Krenmayr, P., Massenspektrometrische untersuchung des substituenteneffektes bei einfach substituierten benzophenonen, Monatsh. Chem., 1974, 105, 787. [all data]

Benoit, 1973
Benoit, F., The benzoyl cation: The participation of isolated electronic excited states in the dissociation of molecular ions of the form [C6H5COX]+, Org. Mass Spectrom., 1973, 7, 1407. [all data]

Iskakov and Potapov, 1971
Iskakov, L.I.; Potapov, V.K., Photionization and decomposition of benzaldehyde, acetophenone, and benzophenone, High Energy Chem., 1971, 5, 238, In original 265. [all data]

Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L., Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. II. Diphenylcarbonyls and ethers, J. Phys. Chem., 1965, 69, 2943. [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

McAlduff and Bunbury, 1979
McAlduff, E.J.; Bunbury, D.L., Photoelectron spectra of some aromatic mono-and di-ketones, J. Electron Spectrosc. Relat. Phenom., 1979, 17, 81. [all data]

Centineo, Fragala, et al., 1978
Centineo, G.; Fragala, I.; Bruno, G.; Spampinato, S., Photoelectron spectroscopy of benzophenone, acetophenone and their ortho-alkyl derivatives, J. Mol. Struct., 1978, 44, 203. [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, References