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Benzaldehyde, 4-hydroxy-

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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:
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Deltasub102.5 ± 0.5kJ/molMERibeiro da Silva, Gonçalves, et al., 2010Based on data from 324. - 341. K.; AC
Deltasub99.7 ± 0.4kJ/molCBernardes and Minas da Piedade, 2008AC
Deltasub98.2 ± 1.3kJ/molN/AStephenson and Malanowski, 1987Based on data from 303. - 336. K. See also Parsons, Rochester, et al., 1971.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
72.3409.AStephenson and Malanowski, 1987Based on data from 394. - 583. K. See also Stull, 1947.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
394.3 - 583.5.321162851.945-46.329Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
101.8 ± 0.5333.MERibeiro da Silva, Gonçalves, et al., 2010Based on data from 324. - 341. K.; AC
91.2324.N/AAihara, 1960Based on data from 312. - 336. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
20.3390.8DSCBernardes and Minas da Piedade, 2008AC
21.6390.8N/ATemprado, Roux, et al., 2008AC

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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, 4-hydroxy- = (Bromine anion bullet Benzaldehyde, 4-hydroxy-)

By formula: Br- + C7H6O2 = (Br- bullet C7H6O2)

Quantity Value Units Method Reference Comment
Deltar108. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M,M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar67.4 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
64.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
67.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C7H5O2- + Hydrogen cation = Benzaldehyde, 4-hydroxy-

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Deltar1393. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1364. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 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)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
1.9×10+68600.MN/AIt is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states.

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 as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference Comment
9.32 ± 0.02EIFoffani, Pignataro, et al., 1964RDSH

De-protonation reactions

C7H5O2- + Hydrogen cation = Benzaldehyde, 4-hydroxy-

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Deltar1393. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1364. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Ion clustering 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Bromine anion + Benzaldehyde, 4-hydroxy- = (Bromine anion bullet Benzaldehyde, 4-hydroxy-)

By formula: Br- + C7H6O2 = (Br- bullet C7H6O2)

Quantity Value Units Method Reference Comment
Deltar108. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M,M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar67.4 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
64.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
67.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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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Mass 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, 1994
NIST MS number 135511

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, Eugeny B. Stern, Antonina A. Goncharova, 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 Grammaticakis, 1953
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. 3310
Instrument n.i.g.
Melting point 117

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

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Column type Active phase Temperature (C) I Reference Comment
PackedOV-101140.1318.6Righezza, Hassani, et al., 1996N2, Chromosorb G HP; Column length: 5. m
PackedOV-101160.1320.8Hassani and Meklati, 1992N2, Chromosorb G HP; Column length: 5. m
CapillarySE-30160.1320.Evans and Haken, 1989Column length: 25. m; Column diameter: 0.32 mm
CapillarySE-30160.1320.Korhonen and Knuutinen, 1984N2; Column length: 25. m; Column diameter: 0.3 mm
CapillarySE-30180.1318.Korhonen and Knuutinen, 1984N2; Column length: 25. m; Column diameter: 0.3 mm
CapillarySE-30200.1302.Korhonen and Knuutinen, 1984N2; Column length: 25. m; Column diameter: 0.3 mm

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

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Column type Active phase I Reference Comment
PackedSE-301311.Staniewski, 1991GasChrom Q, 4. K/min; Column length: 2. m; Tstart: 80. C; Tend: 250. C
CapillaryDB-11317.Wu, Kuo, et al., 199150. m/0.32 mm/1.05 «mu»m, He, 2. K/min, 260. C @ 40. min; Tstart: 40. C
CapillarySE-301324.Korhonen and Knuutinen, 1984N2, 10. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tstart: 100. C
CapillarySE-301308.Korhonen and Knuutinen, 1984N2, 14. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tstart: 100. C
CapillarySE-301318.Korhonen and Knuutinen, 1984N2, 6. K/min; Column length: 25. m; Column diameter: 0.3 mm; Tstart: 100. C

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

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Column type Active phase I Reference Comment
CapillaryHP-Innowax2958.Adamiec, Cejpek, et al., 200130. m/0.25 mm/0.25 «mu»m, N2, 5. K/min; Tstart: 60. C; Tend: 220. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryHP-11323.Castel, Fernandez, et al., 200650. m/0.2 mm/0.5 «mu»m, He, 2. K/min, 250. C @ 120. min; Tstart: 60. C

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

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone1320.Feng, Yue, et al., 2006Program: not specified

References

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

Ribeiro da Silva, Gonçalves, et al., 2010
Ribeiro da Silva, Maria D.M.C.; Gonçalves, Mariana V.; Monte, Manuel J.S., Thermodynamic study on hydroxybenzaldehyde derivatives: 3- and 4-Hydroxybenzaldehyde isomers and 3,5-di-tert-butyl-2-hydroxybenzaldehyde, The Journal of Chemical Thermodynamics, 2010, 42, 4, 472-477, https://doi.org/10.1016/j.jct.2009.10.009 . [all data]

Bernardes and Minas da Piedade, 2008
Bernardes, Carlos E.S.; Minas da Piedade, Manuel E., Energetics of the O-H Bond and of Intramolecular Hydrogen Bonding in HOC 6 H 4 C(O)Y (Y = H, CH 3 , CH 2 CH«58875»CH 2 , C«58876»CH, CH 2 F, NH 2 , NHCH 3 , NO 2 , OH, OCH 3 , OCN, CN, F, Cl, SH, and SCH 3 ) Compounds, J. Phys. Chem. A, 2008, 112, 40, 10029-10039, https://doi.org/10.1021/jp804455u . [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]

Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C., Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion, J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533 . [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]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols, Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194 . [all data]

Temprado, Roux, et al., 2008
Temprado, M.; Roux, María Victoria; Chickos, J.S., Some thermophysical properties of several solid aldehydes, J Therm Anal Calorim, 2008, 94, 1, 257-262, https://doi.org/10.1007/s10973-007-8883-0 . [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [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]

Grammaticakis, 1953
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'U.-V. moyen et le visible de quelques aldehydes et cetones aromatiques ainsi que de certains de leurs derives fonctionnels, (Premier memoire), Bull. Soc. Chim. Fr., 1953, 20, 821-826. [all data]

Righezza, Hassani, et al., 1996
Righezza, M.; Hassani, A.; Meklati, B.Y.; Chrétien, J.R., Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatography, J. Chromatogr. A, 1996, 723, 1, 77-91, https://doi.org/10.1016/0021-9673(95)00816-0 . [all data]

Hassani and Meklati, 1992
Hassani, A.; Meklati, B.Y., Gas chromatographic behaviour of monosubstituted benzenes, benzaldehydes and acetophenones on OV polymethylphenyl-silicone stationary phases, Chromatographia, 1992, 33, 5/6, 267-271, https://doi.org/10.1007/BF02276193 . [all data]

Evans and Haken, 1989
Evans, M.B.; Haken, J.K., Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds, J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5 . [all data]

Korhonen and Knuutinen, 1984
Korhonen, I.O.O.; Knuutinen, J., Gas-liquid chromatographic analyses. XXVII. Separation of chlorinated 4-hydroxybenzaldehydes on a capillary column coated with non-polar SE-30 stationary phase, J. Chromatogr., 1984, 292, 2, 345-353, https://doi.org/10.1016/S0021-9673(01)83614-1 . [all data]

Staniewski, 1991
Staniewski, J., Gas chromatographic analysis of some hydroxyoxime extractants of metals, Chem. Anal. (Warsaw), 1991, 36, 2, 325-333. [all data]

Wu, Kuo, et al., 1991
Wu, P.; Kuo, M.-C.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T., Free and glycosidically bound aroma compounds in pineapple (Ananas comosus L. Merr.), J. Agric. Food Chem., 1991, 39, 1, 170-172, https://doi.org/10.1021/jf00001a033 . [all data]

Adamiec, Cejpek, et al., 2001
Adamiec, J.; Cejpek, K.; Rossner, J.; Velisek, J., Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine, Czech. J. Food. Sci., 2001, 19, 1, 13-18. [all data]

Castel, Fernandez, et al., 2006
Castel, C.; Fernandez, X.; Lizzani-Cuvelier, L.; Perichet, C.; Lavoine, S., Characterization of the Chemical Composition of a Byproduct from Siam Benzoin Gum, J. Agric. Food Chem., 2006, 54, 23, 8848-8854, https://doi.org/10.1021/jf061193y . [all data]

Feng, Yue, et al., 2006
Feng, C.-J.; Yue, W.; Li, M.-J., Estimation of chromatographic retention index of chlorinated hydroxybenzaldehyde by correlation indexes, Chem. Ind. Engineering, 2006, 23, 6, 486-490. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References