Benzaldehyde

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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - 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

Bromine anion + Benzaldehyde = (Bromine anion • Benzaldehyde)

By formula: Br- + C7H6O = (Br- • C7H6O)

Quantity Value Units Method Reference Comment
Δr55.2kJ/molPHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr84.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
20.423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Nitric oxide anion + Benzaldehyde = (Nitric oxide anion • Benzaldehyde)

By formula: NO- + C7H6O = (NO- • C7H6O)

Quantity Value Units Method Reference Comment
Δr183.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Benzaldehyde + perbenzoic acid = 2Benzoic acid

By formula: C7H6O + C7H6O3 = 2C7H6O2

Quantity Value Units Method Reference Comment
Δr-316. ± 13.kJ/molCmBriner and Chastonay, 1954liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -317. ± 13. kJ/mol; ALS

Benzaldehyde + Acetophenone = Water + Chalcone

By formula: C7H6O + C8H8O = H2O + C15H12O

Quantity Value Units Method Reference Comment
Δr-65.0 ± 1.9kJ/molCmHao, Chang, et al., 1985liquid phase; solvent: Aqueous NaOH; ALS

Hydrogen iodide + Benzoyl iodide = Benzaldehyde + Iodine

By formula: HI + C7H5IO = C7H6O + I2

Quantity Value Units Method Reference Comment
Δr-13. ± 4.2kJ/molEqkSolly and Benson, 1971gas phase; ALS

Benzaldehyde + Iodine = Hydrogen iodide + Benzoyl iodide

By formula: C7H6O + I2 = HI + C7H5IO

Quantity Value Units Method Reference Comment
Δr13. ± 4.2kJ/molEqkSolly and Benson, 1971gas phase; ALS

Benzaldehyde, phenylhydrazone + Water = Benzaldehyde + Hydrazine, phenyl-

By formula: C13H12N2 + H2O = C7H6O + C6H8N2

Quantity Value Units Method Reference Comment
Δr-61.1kJ/molCmLandrieu, 1905solid phase; ALS

Benzyl alcohol = Benzaldehyde + Hydrogen

By formula: C7H8O = C7H6O + H2

Quantity Value Units Method Reference Comment
Δr53.93kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

perbenzoic acid = Benzaldehyde + Oxygen

By formula: C7H6O3 = C7H6O + O2

Quantity Value Units Method Reference Comment
Δr253.kJ/molCmBriner and Chastonay, 1954solid phase; ALS

Gas phase ion energetics data

Go To: Top, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C7H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.50 ± 0.08eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)834.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity802.1kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.4293 ± 0.0087ECDWentworth, Kao, et al., 1975B
0.421 ± 0.010ECDWentworth and Chen, 1967B
0.390 ± 0.050ECDZlatkis, Lee, et al., 1983B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
831.7 ± 1.3Fernandez, Jennings, et al., 1989T = 573 - 725K; Reference Sprot(C2H5)2O = 17.0 J/mol K in Hunter and Lias, 1998 needs to be re-evaluated. Using Sprot(C6H5CHO) = 2 J/mol K from Hunter and Lias, 1998, this measurement yields Sprot((C2H5)2O = 8 J/mol K.; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
802.5 ± 3.4Fernandez, Jennings, et al., 1989T = 573 - 725K; Reference Sprot(C2H5)2O = 17.0 J/mol K in Hunter and Lias, 1998 needs to be re-evaluated. Using Sprot(C6H5CHO) = 2 J/mol K from Hunter and Lias, 1998, this measurement yields Sprot((C2H5)2O = 8 J/mol K.; MM

Protonation entropy at 298K

Protonation entropy (J/mol*K) Reference Comment
11.Fernandez, Jennings, et al., 1989T = 573 - 725K; Reference Sprot(C2H5)2O = 17.0 J/mol K in Hunter and Lias, 1998 needs to be re-evaluated. Using Sprot(C6H5CHO) = 2 J/mol K from Hunter and Lias, 1998, this measurement yields Sprot((C2H5)2O = 8 J/mol K.; MM

Ionization energy determinations

IE (eV) Method Reference Comment
~9.35PEKlasinc, Kovac, et al., 1983LBLHLM
9.49PIMcLoughlin and Traeger, 1979LLK
9.65EIElder, Beynon, et al., 1976LLK
9.49PEBehan, Johnstone, et al., 1976LLK
9.40PERabalais and Colton, 1973LLK
9.74EIBenoit, 1973LLK
9.50 ± 0.02PIIskakov and Potapov, 1971LLK
9.53 ± 0.03EIBock, Alt, et al., 1969RDSH
9.53 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.6PITerenin, 1961RDSH
9.51 ± 0.02PIWatanabe, 1957RDSH
9.60 ± 0.02PIVilesov and Terenin, 1957RDSH
9.71PEGal, Geribaldi, et al., 1985Vertical value; LBLHLM
9.57PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.54PEBenoit and Harrison, 1977Vertical value; LLK
10.0PERao, 1975Vertical value; LLK
9.80PEBaker, May, et al., 1968Vertical value; RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+13.67 ± 0.13?EIReed and Thornley, 1958RDSH
C6H5+14.11CO+HEIBenoit, 1973LLK
C6H5+13.51 ± 0.12CHO?EIReed and Thornley, 1958RDSH
C7H5O+9.93HPIMcLoughlin and Traeger, 1979LLK
C7H5O+11.11HEIElder, Beynon, et al., 1976LLK
C7H5O+11.26HEIBenoit, 1973LLK
C7H5O+10.99HEIHowe and Williams, 1969RDSH

References

Go To: Top, 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.

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Briner and Chastonay, 1954
Briner, E.; Chastonay, P., Etude thermochemique de l'autoxydation de Valdehyde benzoique, Helv. Chim. Acta, 1954, 238, 539-541. [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]

Hao, Chang, et al., 1985
Hao, J.; Chang, J.; Wang, K.; Liu, Y.; Zhong, G., Heat of reaction of chalcone by calorimetric measurement, Huaxue Tongbao, 1985, 15-16. [all data]

Solly and Benson, 1971
Solly, R.K.; Benson, S.W., Thermochemistry of the reaction of benzaldehyde with iodine. The enthalpy of formation of benzaldehyde and benzoyl iodide, J. Chem. Thermodyn., 1971, 3, 203-209. [all data]

Landrieu, 1905
Landrieu, M.Ph., Thermochimie. - Thermochimie des hydrazones, Compt. Rend., 1905, 141, 358-361. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [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]

Wentworth, Kao, et al., 1975
Wentworth, W.E.; Kao, L.W.; Becker, R.S., Electron affinities of substituted aromatic compounds, J. Phys. Chem., 1975, 79, 1161. [all data]

Wentworth and Chen, 1967
Wentworth, W.E.; Chen, E., Experimental Determination of the Electron Affinity of Several Aromatic Aldehydes and Ketones, J. Phys. Chem., 1967, 71, 6, 1929, https://doi.org/10.1021/j100865a063 . [all data]

Zlatkis, Lee, et al., 1983
Zlatkis, A.; Lee, C.K.; Wentworth, W.E.; Chen, E.C.M., Constant current linearization for determination of electron capture mechanisms, Anal. Chem., 1983, 55, 1596. [all data]

Fernandez, Jennings, et al., 1989
Fernandez, T.; Jennings, K.R.; Mason, R.S., Gas-phase proton transfer reactions in xylene-dimethyl ether mixtures, J. Chem. Soc. Faraday Trans. 2, 1989, 85, 1813. [all data]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C., A photoionization study of some benzoyl compounds - thermochemistry of [C7H5O]+ formation, Org. Mass Spectrom., 1979, 14, 434. [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]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Rabalais and Colton, 1973
Rabalais, J.W.; Colton, R.J., Electronic interaction between the phenyl group and its unsaturated substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [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]

Bock, Alt, et al., 1969
Bock, H.; Alt, H.; Seidl, H., d-Orbital effects in silicon-substituted π-electron systems. XV. The color of silyl ketones, J. Am. Chem. Soc., 1969, 91, 355. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

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

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W., Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives, J. Chem. Soc. B, 1968, 22. [all data]

Reed and Thornley, 1958
Reed, R.I.; Thornley, M.B., Studies in electron impact methods. Part 5. Acetaldehyde, acrolein, benzaldehyde, and propionaldehyde, J. Chem. Soc. Faraday Trans., 1958, 54, 949. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References