Benzoic acid, 3-hydroxy-

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-112.1 ± 0.31kcal/molCcrSabbah and Le, 1993ALS
Δfgas-111.3kcal/molN/AColomina, Jimenez, et al., 1980Value computed using ΔfHsolid° value of -590.5±1.0 kj/mol from Colomina, Jimenez, et al., 1980 and ΔsubH° value of 125.0 kj/mol from Sabbah and Le, 1993.; DRB

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-142.0 ± 0.26kcal/molCcrSabbah and Le, 1993ALS
Δfsolid-141.1 ± 0.24kcal/molCcbColomina, Jimenez, et al., 1980ALS
Quantity Value Units Method Reference Comment
Δcsolid-721.30 ± 0.26kcal/molCcrSabbah and Le, 1993Corresponding Δfsolid = -142.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-722.18 ± 0.1kcal/molCcbColomina, Jimenez, et al., 1980Corresponding Δfsolid = -141.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar42.30cal/mol*KN/AParks and Light, 1934Extrapolation below 90 K, 56.48 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
37.60288.4Parks and Light, 1934T = 94 to 288 K. Value is unsmoothed experimental datum.; 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:
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
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tfus472.KN/AMayer, Howell, et al., 1990Uncertainty assigned by TRC = 1.5 K; TRC
Tfus364.KN/AKuhn and Dury, 1951Uncertainty assigned by TRC = 3. K; TRC
Tfus472.KN/AKing, McWhirter, et al., 1945Uncertainty assigned by TRC = 6. K; TRC
Quantity Value Units Method Reference Comment
Δsub28.27 ± 0.26kcal/molCPinto, Diogo, et al., 2005AC
Δsub29.87 ± 0.18kcal/molCSabbah and Le, 1993ALS
Δsub29.88kcal/molN/ASabbah and Le, 1993DRB
Δsub29.88 ± 0.18kcal/molN/ASabbah and Le, 1993AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
29.52 ± 0.18363.CSabbah and Le, 1993AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
8.72476.4Pinto, Diogo, et al., 2005AC
6.26475.1Domalski and Hearing, 1996See also Sabbah and Le, 1993.; AC

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: John E. Bartmess

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

C7H5O3- + Hydrogen cation = Benzoic acid, 3-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr338.6 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr331.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C7H6O3+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.2 ± 0.2EIBenoit, 1973LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5O+14.4 ± 0.2CO+OHEIBenoit, 1973LLK
C7H5O2+12.5 ± 0.2OHEIBenoit, 1973LLK

De-protonation reactions

C7H5O3- + Hydrogen cation = Benzoic acid, 3-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr338.6 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr331.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

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
NIST MS number 365468

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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

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApieson L140.1417.Hedin, Minyard, et al., 1967Nitrogen, Chromosorb W HMDS (60-80 mesh); Column length: 1.8 m

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), Gas Chromatography, Notes

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

Sabbah and Le, 1993
Sabbah, R.; Le, T.H.D., Etude thermodynamique des trois isomeres de l'acide bydroxybenzolque, Can. J. Chem., 1993, 71, 1378-1383. [all data]

Colomina, Jimenez, et al., 1980
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C., Thermochemical properties of o-, m- and p-hydroxybenzoic acids, J. Calorim. Anal. Therm., 1980, 11, 1-6. [all data]

Parks and Light, 1934
Parks, G.S.; Light, D.W., Thermal data on organic compounds. XIII. The heat capacities and entropies of n-tetradecane and the hydroxybenzoic acids. The relative free energies of some benzenoid position isomers, J. Am. Chem. Soc., 1934, 56, 1511-1513. [all data]

Mayer, Howell, et al., 1990
Mayer, M.M.; Howell, W.J.; Tomasko, D.L.; Eckert, C.A., Solid-solid Equilibria in the Systems Thianthrene + Phenanthrene, Salicylic Acid + Phenanthrene, and 3-Hydroxybenzoic Acid + Phenanthrene, J. Chem. Eng. Data, 1990, 35, 446. [all data]

Kuhn and Dury, 1951
Kuhn, R.; Dury, K., 6-Acetylsalicylic acid, Chem. Ber., 1951, 84, 848-50. [all data]

King, McWhirter, et al., 1945
King, L.C.; McWhirter, M.; Barton, D.M., Reactions of Acetophenols with Iodine and Pyridine and the Preparation of Hydroxybenzoic Acids, J. Am. Chem. Soc., 1945, 67, 2089-92. [all data]

Pinto, Diogo, et al., 2005
Pinto, Susana S.; Diogo, Hermínio P.; Guedes, Rita C.; Costa Cabral, Benedito J.; Minas da Piedade, Manuel E.; Martinho Simões, José A., Energetics of Hydroxybenzoic Acids and of the Corresponding Carboxyphenoxyl Radicals. Intramolecular Hydrogen Bonding in 2-Hydroxybenzoic Acid, J. Phys. Chem. A, 2005, 109, 42, 9700-9708, https://doi.org/10.1021/jp054220g . [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]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Benoit, 1973
Benoit, F., Substituent effects in mass spectrometry. III. Substituent effects in the dissociation of the molecular ions of para and meta subtituted benzoic acids, Org. Mass Spectrom., 1973, 7, 295. [all data]

Hedin, Minyard, et al., 1967
Hedin, P.A.; Minyard, J.P.; Thompson, A.C., Chromatographic and spectral analysis of phenolic acids and related compounds, J. Chromatogr., 1967, 30, 43-53, https://doi.org/10.1016/S0021-9673(00)84111-4 . [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), Gas Chromatography, References