Benzoic acid, 3-hydroxy-

• Formula: C₇H₆O₃
• Molecular weight: 138.1207
• IUPAC Standard InChI:
  

  InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10) Download the identifier in a file.

• IUPAC Standard InChIKey: IJFXRHURBJZNAO-UHFFFAOYSA-N
• CAS Registry Number: 99-06-9
• 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: Benzoic acid, m-hydroxy-; m-Hydroxybenzoic acid; m-Salicylic acid; 3-Carboxyphenol; 3-Hydroxybenzoic acid; meta-Hydroxybenzoic acid; Acido m-idrossibenzoico; m-Hba; Kyselina 3-hydroxybenzoova; NSC 55746
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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
fH°gas	-469.1 ± 1.3	kJ/mol	Ccr	Sabbah and Le, 1993	ALS
fH°gas	-465.5	kJ/mol	N/A	Colomina, Jimenez, et al., 1980	Value computed using «DELTA»fHsolid° value of -590.5±1.0 kj/mol from Colomina, Jimenez, et al., 1980 and «DELTA»subH° 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
fH°solid	-594.1 ± 1.1	kJ/mol	Ccr	Sabbah and Le, 1993	ALS
fH°solid	-590.5 ± 1.0	kJ/mol	Ccb	Colomina, Jimenez, et al., 1980	ALS
Quantity	Value	Units	Method	Reference	Comment
cH°solid	-3017.9 ± 1.1	kJ/mol	Ccr	Sabbah and Le, 1993	Corresponding «DELTA»fHºsolid = -594.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°solid	-3021.6 ± 0.4	kJ/mol	Ccb	Colomina, Jimenez, et al., 1980	Corresponding «DELTA»fHºsolid = -590.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°solid,1 bar	177.0	J/mol*K	N/A	Parks and Light, 1934	Extrapolation below 90 K, 56.48 J/mol*K.; DH

Constant pressure heat capacity of solid

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, Kenneth Kroenlein 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
Tfus	472.	K	N/A	Mayer, Howell, et al., 1990	Uncertainty assigned by TRC = 1.5 K; TRC
Tfus	364.	K	N/A	Kuhn and Dury, 1951	Uncertainty assigned by TRC = 3. K; TRC
Tfus	472.	K	N/A	King, McWhirter, et al., 1945	Uncertainty assigned by TRC = 6. K; TRC
Quantity	Value	Units	Method	Reference	Comment
subH°	118.3 ± 1.1	kJ/mol	C	Pinto, Diogo, et al., 2005	AC
subH°	124.99 ± 0.74	kJ/mol	C	Sabbah and Le, 1993	ALS
subH°	125.0	kJ/mol	N/A	Sabbah and Le, 1993	DRB
subH°	125.0 ± 0.74	kJ/mol	N/A	Sabbah and Le, 1993	AC

Enthalpy of sublimation

subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
123.5 ± 0.74	363.	C	Sabbah and Le, 1993	AC

Enthalpy of fusion

fusH (kJ/mol)	Temperature (K)	Reference	Comment
36.5	476.4	Pinto, Diogo, et al., 2005	AC
26.2	475.1	Domalski and Hearing, 1996	See also Sabbah and Le, 1993.; AC

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^- +  =

By formula: C₇H₅O₃^- + H⁺ = C₇H₆O₃

Quantity	Value	Units	Method	Reference	Comment
rH°	1417. ± 8.8	kJ/mol	G+TS	Kebarle and McMahon, 1977	gas phase
Quantity	Value	Units	Method	Reference	Comment
rG°	1387. ± 8.4	kJ/mol	IMRE	Kebarle and McMahon, 1977	gas phase

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (SPLIT MULL); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

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]

Notes

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

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tfus	Fusion (melting) point
  cH°solid	Enthalpy of combustion of solid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°solid	Enthalpy of formation of solid at standard conditions
  fusH	Enthalpy of fusion
  rG°	Free energy of reaction at standard conditions
  rH°	Enthalpy of reaction at standard conditions
  subH	Enthalpy of sublimation
  subH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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