Maleic anhydride

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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: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
20.06273.15Caminati W., 1985Other statistically calculated values are: S(298.15 K)=300.75 J/mol*K and Cp(298.15 K)=88.87 J/mol*K [ Joshi R.M., 1970].
21.52298.15
30.722500.
38.157800.

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-112.43 ± 0.17kcal/molCcbWilhoit and Shiao, 1964ALS
Δfsolid-112.23 ± 0.06kcal/molCcbParks, Mosley, et al., 1950ALS
Quantity Value Units Method Reference Comment
Δcsolid-332.09 ± 0.16kcal/molCcbWilhoit and Shiao, 1964Corresponding Δfsolid = -112.43 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-332.29 ± 0.17kcal/molCcbParks, Mosley, et al., 1950Corresponding Δfsolid = -112.23 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
28.66300.DeWit, DeKruif, et al., 1983T = 90 to 350 K. Linearly extrapolated.; DH
29.45310.DeWit, Offringa, et al., 1983T = 300 to 450 K.; DH
16.1298.15Marchidan and Ciopec, 1978T = 298 to 480 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
AC - William E. Acree, Jr., James S. Chickos
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
Tboil473.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus326.0 ± 0.9KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple325.72KN/ADe Wit, De Kruif, et al., 1983Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Δsub17.kcal/molN/AVilcu, Perisanu, et al., 1978AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
11.7351.AStephenson and Malanowski, 1987Based on data from 336. to 475. K.; AC
13.1325.8VWinstrom and Kulp, 1949ALS
13.1326. to 350.N/AWinstrom and Kulp, 1949, 2AC
13.6332.N/AStull, 1947Based on data from 317. to 475. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
317. to 475.3.793451431.009-101.093Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
20.4317.N/AStephenson and Malanowski, 1987Based on data from 308. to 326. K.; AC
16.4258.TE,MEDe Wit, Van Miltenburg, et al., 1983AC
17.1 ± 1.2308. to 325.N/AWinstrom and Kulp, 1949, 2See also Cox and Pilcher, 1970.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
3.2385325.72DeWit, DeKruif, et al., 1983DH
3.2620326.00Mastrangelo, 1957DH
3.2505325.3DeWit, Offringa, et al., 1983DH
2.930325.7Domalski and Hearing, 1996AC
3.0903325.Spengler and Tamplin, 1952DH
2.9302325.64Marchidan and Ciopec, 1978DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
9.94325.72DeWit, DeKruif, et al., 1983DH
9.99325.3DeWit, Offringa, et al., 1983DH
9.51325.Spengler and Tamplin, 1952DH
8.99325.64Marchidan and Ciopec, 1978DH

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

Maleic anhydride + 1,3-Cyclopentadiene = Carbic anhydride

By formula: C4H2O3 + C5H6 = C9H8O3

Quantity Value Units Method Reference Comment
Δr-24.8 ± 0.5kcal/molCmBreslauer and Kabakoff, 1974liquid phase; solvent: Dioxane
Δr-25.78kcal/molCmRogers and Quan, 1973liquid phase; Gas phase Diels-Alder

Maleic anhydride + Anthracene = Anthracene-maleic anhydride Diels-Alder adduct

By formula: C4H2O3 + C14H10 = C18H12O3

Quantity Value Units Method Reference Comment
Δr-22. ± 0.5kcal/molCmKiselev, Mavrin, et al., 1982liquid phase; solvent: Benzene
Δr-22.4kcal/molEqkLenz, Hegedus, et al., 1982liquid phase; solvent: 1,2,4-C6H3Cl3

Maleic anhydride + Furan, 2-methyl- = 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1-methyl-, exo

By formula: C4H2O3 + C5H6O = C9H8O4

Quantity Value Units Method Reference Comment
Δr-14.0kcal/molCmBalbi, 1991liquid phase; solvent: Dioxane
Δr-14.kcal/molCmSparks and Poling, 1983solid phase; solvent: Dioxane

Maleic anhydride + Water = Maleic acid

By formula: C4H2O3 + H2O = C4H4O4

Quantity Value Units Method Reference Comment
Δr-8.3 ± 0.2kcal/molCmConn, Kistiakowsky, et al., 1942liquid phase; Heat of hydroysis at 303 K

Maleic anhydride + Anthracene, 9-phenyl- = C24H16O3

By formula: C4H2O3 + C20H14 = C24H16O3

Quantity Value Units Method Reference Comment
Δr-102.1kcal/molEqkLenz, Hegedus, et al., 1982liquid phase; solvent: 1,2,4-C6H3Cl3

1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro- = 1,3-Butadiene + Maleic anhydride

By formula: C8H8O3 = C4H6 + C4H2O3

Quantity Value Units Method Reference Comment
Δr67.79 ± 0.23kcal/molCmGhitau, Ciopec, et al., 1983solid phase; At 65 to 90°C

Maleic anhydride + 1-Butanol = 2-Butenedioic acid (Z)-, monobutyl ester

By formula: C4H2O3 + C4H10O = C8H12O4

Quantity Value Units Method Reference Comment
Δr-9.3kcal/molKinMerca, Poraicu, et al., 1978solid phase; solvent: n-Butanol; DTA

1,3-Butadiene + Maleic anhydride = 1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-

By formula: C4H6 + C4H2O3 = C8H8O3

Quantity Value Units Method Reference Comment
Δr-67.788kcal/molCmGhitau, Ciopec, et al., 1983liquid phase

Maleic anhydride + 1-Propanol = propyl hydrogen maleate

By formula: C4H2O3 + C3H8O = propyl hydrogen maleate

Quantity Value Units Method Reference Comment
Δr-8.4kcal/molKinTribunescu, Poraicu, et al., 1978liquid phase

Benzenamine, 4-bromo- + Maleic anhydride = 2-Butenoic acid, 4-[(4-bromophenyl)amino]-4-oxo, (Z)-

By formula: C6H6BrN + C4H2O3 = C10H8BrNO3

Quantity Value Units Method Reference Comment
Δr3.4kcal/molCmSrivastava, 1979solid phase

p-Chloroaniline + Maleic anhydride = Maleanilic acid, 4' chloro-

By formula: C6H6ClN + C4H2O3 = C10H8ClNO3

Quantity Value Units Method Reference Comment
Δr3.1kcal/molCmSrivastava, 1979solid phase

Chlorendic anhydride = Maleic anhydride + Hexachlorocyclopentadiene

By formula: C9H2Cl6O3 = C4H2O3 + C5Cl6

Quantity Value Units Method Reference Comment
Δr75.2kcal/molIonVijayakumar and Fink, 1983solid phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

Electron affinity determinations

EA (eV) Method Reference Comment
1.440 ± 0.087TDEqPaul and Kebarle, 1989ΔGea(423 K) = -32.8±1 kcal/mol, ΔS = -1±3 eu.; B
1.440 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -32.7 kcal/mol; ΔSea =-1.3, est. from data in Paul and Kebarle, 1989; B
1.40 ± 0.20NBIECompton, Reinhardt, et al., 1974Lifetime: Cooper and Compton, 1973; B

Ionization energy determinations

IE (eV) Method Reference Comment
11.07PEKimura, Katsumata, et al., 1981Vertical value; LLK
11.11 ± 0.05PEGalasso, Colonna, et al., 1977Vertical value; LLK
11.1PEAlmemark, Backvall, et al., 1974Vertical value; LLK
11.45PEBain and Frost, 1973Vertical value; LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


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-1870
NIST MS number 227705

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.


UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Boule and Lemaire, 1977
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 17664
Instrument unknown
Melting point 52.8
Boiling point 202

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), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Caminati W., 1985
Caminati W., A study of the ring-bending and ring-twisting motions in maleic anhydride by rotational analysis of the corresponding vibrational satellites, Spectrochim. Acta, 1985, A41, 937-941. [all data]

Joshi R.M., 1970
Joshi R.M., Thermodynamic properties of some monomeric compounds in the standard ideal gas state, J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]

Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D., Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids., J. Chem. Eng. Data, 1964, 9, 595-599. [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]

DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodynam., 1983, 15, 891-902. [all data]

DeWit, Offringa, et al., 1983
DeWit, H.G.M.; Offringa, J.C.A.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen and sulfur. III. Molar heat capacities measured by differential scanning calorimetry, Thermochim. Acta, 1983, 65, 43-51. [all data]

Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M., Thermodynamic properties of maleic, trimellitic and pyromellitic anhydrides, Rev. Roum. Chim., 1978, 23, 19-29. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

De Wit, De Kruif, et al., 1983
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodyn., 1983, 15, 9, 891, https://doi.org/10.1016/0021-9614(83)90095-2 . [all data]

Vilcu, Perisanu, et al., 1978
Vilcu, R.; Perisanu, S.; Ciocazanu, I., The thermochemical properties of some organic anhydrides, Bull. Inst. Politeh. Gheorghe Gheorghiu-Dej, Bucur., Ser. Chim.-Metal., 1978, 40, 2, 9. [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]

Winstrom and Kulp, 1949
Winstrom, L.O.; Kulp, L., Vapor pressure of maleic anhydride, Ind. Eng. Chem., 1949, 41, 1584-25. [all data]

Winstrom and Kulp, 1949, 2
Winstrom, Leon O.; Kulp, Laurence, Vapor Pressure of Maleic Anhydride - Temperature Range from 35° to 77°, Ind. Eng. Chem., 1949, 41, 11, 2584-2586, https://doi.org/10.1021/ie50479a044 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Mastrangelo, 1957
Mastrangelo, S.V.R., Adiabatic calorimeter for determination of cryoscopic data, Anal. Chem., 1957, 29(5), 841-845. [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]

Spengler and Tamplin, 1952
Spengler, H.T.; Tamplin, W.S., Procedures in ice calorimetry, Anal. Chem., 1952, 24, 941-944. [all data]

Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S., Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride, J. Org. Chem., 1974, 39, 721-722. [all data]

Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W., Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride, J. Phys. Chem., 1973, 77, 828-831. [all data]

Kiselev, Mavrin, et al., 1982
Kiselev, V.D.; Mavrin, G.V.; Konovalov, A.I., Thermodynamic principles of the occurrence of a Diels-Alder reaction in the presence of a Lewis acid, Zh. Org. Khim., 1982, 18, 2505-2510. [all data]

Lenz, Hegedus, et al., 1982
Lenz, T.G.; Hegedus, L.S.; Vaughan, J.D., Liquid phase thermochemical energy conversion systems - an application of Diels-Alder chemistry, Int. J. Energy Res., 1982, 6, 357-365. [all data]

Balbi, 1991
Balbi, N., Dynamic calorimetry in the study of Diels-Alder reaction, Calorim. Anal. Therm., 1991, 22, 299-304. [all data]

Sparks and Poling, 1983
Sparks, B.G.; Poling, B.E., Energy storage capacity of reversible liquid-phase Diels Alder reaction between maleic anhydride and 2-methyl furan, Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1983, 29, 534-537. [all data]

Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A., Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides, J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]

Ghitau, Ciopec, et al., 1983
Ghitau, M.; Ciopec, M.; Pintea, O., Study on Diels-Alder reaction for the synthesis of tetrahydrophthalic anhydride, Rev. Chim. (Bucharest), 1983, 34, 299-305. [all data]

Merca, Poraicu, et al., 1978
Merca, E.; Poraicu, M.; Tribunescu, P., Kinetics of maleic monoester formation with n-butanol, Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 160-163. [all data]

Tribunescu, Poraicu, et al., 1978
Tribunescu, P.; Poraicu, M.; Merca, E.; Facsko, O., Kinetics of mono-N-propylmaleate synthesis, Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 147-151. [all data]

Srivastava, 1979
Srivastava, A.K., Solid-state reactions between maleic anhydride and substituted aromactic amines, Z. Phys. Chem. (Leipzig), 1979, 260, 630-640. [all data]

Vijayakumar and Fink, 1983
Vijayakumar, C.T.; Fink, J.K., Heat of formation of the Diels-Alder adduct of hexachlorocyclopentadiene and maleic anhydride by appearance-energy measurements, Org. Mass Spectrom., 1983, 18, 134. [all data]

Paul and Kebarle, 1989
Paul, G.; Kebarle, P., Electron Affinities of Cyclic Unsaturated Dicarbonyls: Maleic Anhydrides, Maleimides, and Cyclopentendione, J. Am. Chem. Soc., 1989, 111, 2, 464, https://doi.org/10.1021/ja00184a009 . [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]

Compton, Reinhardt, et al., 1974
Compton, R.N.; Reinhardt, P.W.; Cooper, C.D., Mass spectrometry utilizing collisional ionization of cesium: Maleic anhydride and succinic anhydride, J. Chem. Phys., 1974, 60, 2953. [all data]

Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N., Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities, J. Chem. Phys., 1973, 59, 3550. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Galasso, Colonna, et al., 1977
Galasso, V.; Colonna, F.P.; Distefano, G., Photoelectron spectra of 1,2-indandione, 1,3-indandione and heterocyclic analogues, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 227. [all data]

Almemark, Backvall, et al., 1974
Almemark, M.; Backvall, J.E.; Moberg, C.A.; Akermark, B.; Asbrink, L.; Roos, B., Ab initio calculations and assignment of photoelectron spectra of maleic and succinic anhydride, Tetrahedron, 1974, 30, 2503. [all data]

Bain and Frost, 1973
Bain, A.D.; Frost, D.C., Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy, Can. J. Chem., 1973, 51, 1245. [all data]

Boule and Lemaire, 1977
Boule, P.; Lemaire, J., Compt. rend., 1977, 285, 305. [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), UV/Visible spectrum, References