Benzaldehyde
- Formula: C7H6O
- Molecular weight: 106.1219
- IUPAC Standard InChIKey: HUMNYLRZRPPJDN-UHFFFAOYSA-N
- CAS Registry Number: 100-52-7
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Artificial Almond Oil; Benzaldehyde FFC; Benzenecarbonal; Benzenecarboxaldehyde; Benzoic aldehyde; Phenylmethanal; Almond artificial essential oil; Phenylmethanal benzenecarboxaldehyde; NCI-C56133; Oil of Bitter Almond; Artificial essential oil of almond; Benzene carbaldehyde; NA 1989; Artifical essential oil of almond; Artificial bitter almond oil; Benzenemethylal; Benzoyl hydride; Ethereal oil of bitter almonds; Benzylaldehyde; NSC 7917; Benzyaldehyde
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Reaction thermochemistry data
Go To: Top, Henry's Law data, Gas phase ion energetics data, 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 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
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Individual Reactions
By formula: Br- + C7H6O = (Br- • C7H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.2 | kJ/mol | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
20. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
By formula: NO- + C7H6O = (NO- • C7H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 183. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
By formula: C7H6O + C7H6O3 = 2C7H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -316. ± 13. | kJ/mol | Cm | Briner and Chastonay, 1954 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -317. ± 13. kJ/mol; ALS |
By formula: C7H6O + C8H8O = H2O + C15H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -65.0 ± 1.9 | kJ/mol | Cm | Hao, Chang, et al., 1985 | liquid phase; solvent: Aqueous NaOH; ALS |
By formula: HI + C7H5IO = C7H6O + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13. ± 4.2 | kJ/mol | Eqk | Solly and Benson, 1971 | gas phase; ALS |
By formula: C7H6O + I2 = HI + C7H5IO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13. ± 4.2 | kJ/mol | Eqk | Solly and Benson, 1971 | gas phase; ALS |
By formula: C13H12N2 + H2O = C7H6O + C6H8N2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -61.1 | kJ/mol | Cm | Landrieu, 1905 | solid phase; ALS |
By formula: C7H8O = C7H6O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.93 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
By formula: C7H6O3 = C7H6O + O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 253. | kJ/mol | Cm | Briner and Chastonay, 1954 | solid phase; ALS |
Henry's Law data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
39. | 4800. | L | N/A | |
42. | 4600. | M | N/A | The data from Table 1 by missing citation was used to redo the regression analysis. The data for acetone in their Table 2 is wrong. |
37. | 5100. | M | N/A | missing citation list effective values that take into account hydration of the aldehydes: kH = ([RCHO] + [RCH(OH)2]) / p(RCHO) |
36. | X | N/A | Value given here as quoted by missing citation. | |
36. | V | N/A |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Henry's Law data, 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 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 ± 0.08 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 834.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 802.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.4293 ± 0.0087 | ECD | Wentworth, Kao, et al., 1975 | B |
0.421 ± 0.010 | ECD | Wentworth and Chen, 1967 | B |
0.390 ± 0.050 | ECD | Zlatkis, Lee, et al., 1983 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
831.7 ± 1.3 | Fernandez, Jennings, et al., 1989 | T = 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 ± 3.4 | Fernandez, Jennings, et al., 1989 | T = 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., 1989 | T = 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 |
---|---|---|---|
~9.35 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
9.49 | PI | McLoughlin and Traeger, 1979 | LLK |
9.65 | EI | Elder, Beynon, et al., 1976 | LLK |
9.49 | PE | Behan, Johnstone, et al., 1976 | LLK |
9.40 | PE | Rabalais and Colton, 1973 | LLK |
9.74 | EI | Benoit, 1973 | LLK |
9.50 ± 0.02 | PI | Iskakov and Potapov, 1971 | LLK |
9.53 ± 0.03 | EI | Bock, Alt, et al., 1969 | RDSH |
9.53 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.6 | PI | Terenin, 1961 | RDSH |
9.51 ± 0.02 | PI | Watanabe, 1957 | RDSH |
9.60 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
9.71 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
9.57 | PE | Klasinc, Kovac, et al., 1983 | Vertical value; LBLHLM |
9.54 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
10.0 | PE | Rao, 1975 | Vertical value; LLK |
9.80 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 13.67 ± 0.13 | ? | EI | Reed and Thornley, 1958 | RDSH |
C6H5+ | 14.11 | CO+H | EI | Benoit, 1973 | LLK |
C6H5+ | 13.51 ± 0.12 | CHO? | EI | Reed and Thornley, 1958 | RDSH |
C7H5O+ | 9.93 | H | PI | McLoughlin and Traeger, 1979 | LLK |
C7H5O+ | 11.11 | H | EI | Elder, Beynon, et al., 1976 | LLK |
C7H5O+ | 11.26 | H | EI | Benoit, 1973 | LLK |
C7H5O+ | 10.99 | H | EI | Howe and Williams, 1969 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Reaction thermochemistry data, Henry's Law data, 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 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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118651 |
References
Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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