Resorcinol
- Formula: C6H6O2
- Molecular weight: 110.1106
- IUPAC Standard InChI: InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
- IUPAC Standard InChIKey: GHMLBKRAJCXXBS-UHFFFAOYSA-N
- CAS Registry Number: 108-46-3
- 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: 1,3-Benzenediol; α-Resorcinol; m-Benzenediol; m-Dihydroxybenzene; m-Dioxybenzene; m-Hydroquinone; m-Hydroxyphenol; Benzene, 1,3-dihydroxy-; C.I. Developer 4; C.I. Oxidation Base 31; C.I. 76505; Developer O; Developer R; Developer RS; Durafur Developer G; Fouramine RS; Fourrine EW; Fourrine 79; Nako TGG; Pelagol Grey RS; Pelagol RS; Resorcin; 1,3-Dihydroxybenzene; 3-Hydroxyphenol; Benzene, m-dihydroxy-; Phenol, m-hydroxy-; NCI-C05970; Rcra waste number U201; Resorcine; UN 2876; NSC 1571; Rodol RS; 1,3-Dihydroxybenzene (resorcinol)
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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.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -68.04 ± 0.29 | kcal/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.25±0.52 kJ/mol; ALS |
| ΔfH°gas | -65.7 | kcal/mol | Ccb | Desai, Wilhoit, et al., 1968 | ALS |
| ΔfH°gas | -63.38 | kcal/mol | N/A | Pushin, 1954 | Value computed using ΔfHsolid° value of -351.2 kj/mol from Pushin, 1954 and ΔsubH° value of 86.0 kj/mol from Sabbah and Buluku, 1991.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.291 | 50. | Kudchadker S.A., 1979 | GT |
| 11.34 | 100. | ||
| 15.73 | 150. | ||
| 20.42 | 200. | ||
| 27.304 | 273.15 | ||
| 29.577 | 298.15 | ||
| 29.742 | 300. | ||
| 37.928 | 400. | ||
| 44.422 | 500. | ||
| 49.410 | 600. | ||
| 53.286 | 700. | ||
| 56.381 | 800. | ||
| 58.920 | 900. | ||
| 61.047 | 1000. | ||
| 62.851 | 1100. | ||
| 64.400 | 1200. | ||
| 65.736 | 1300. | ||
| 66.893 | 1400. | ||
| 67.904 | 1500. |
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 |
|---|---|---|---|---|---|
| ΔfH°solid | -88.60 ± 0.26 | kcal/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.25±0.52 kJ/mol; ALS |
| ΔfH°solid | -87.95 ± 0.12 | kcal/mol | Ccb | Desai, Wilhoit, et al., 1968 | crystal phase; ALS |
| ΔfH°solid | -83.94 | kcal/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-85.6 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -680.66 ± 0.26 | kcal/mol | Ccr | Sabbah and Buluku, 1991 | ΔHfusion =15.25±0.52 kJ/mol; Corresponding ΔfHºsolid = -88.60 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -681.30 ± 0.10 | kcal/mol | Ccb | Desai, Wilhoit, et al., 1968 | crystal phase; Corresponding ΔfHºsolid = -87.95 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -685.3 | kcal/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-85.6 kcal/mol; Corresponding ΔfHºsolid = -84.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -683.9 | kcal/mol | Ccb | Barker, 1925 | Author was aware that data differs from previously reported values; Corresponding ΔfHºsolid = -85.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 32.392 | 298.15 | Bret-Dibat and Lichanot, 1989 | T = 200 to 500 K. Cp(c) = 126.876 + 0.3316t + 5.6228x10-4t2 + 9.5321x10-6t3 J/mol*K (t/°C). Cp value caluclated from equation.; DH |
| 33.29 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
| 36.09 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
| 31.31 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 200°C.; DH |
| 31.41 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; DH |
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
C6H5O2- + =
By formula: C6H5O2- + H+ = C6H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 346.6 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
| ΔrH° | 345.2 ± 2.6 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 339.8 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
| ΔrG° | 338.3 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas 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
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H6O2+ (ion structure unspecified)
Proton affinity at 298K
| Proton affinity (kcal/mol) | Reference | Comment |
|---|---|---|
| 204.7 | Bouchoux, Defaye, et al., 2002 | T = 444-504K; MM |
Protonation entropy at 298K
| Protonation entropy (cal/mol*K) | Reference | Comment |
|---|---|---|
| -3.6 | Bouchoux, Defaye, et al., 2002 | T = 444-504K; MM |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.2 | PE | Palmer, Moyes, et al., 1979 | LLK |
| 8.63 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
De-protonation reactions
C6H5O2- + =
By formula: C6H5O2- + H+ = C6H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 346.6 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 345.2 ± 2.6 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 339.8 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 338.3 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
Sabbah and Buluku, 1991
Sabbah, R.; Buluku, E.N.L.E.,
Thermodynamic study of three isomers of dihydroxybenzene,
Can. J. Chem., 1991, 69, 481-488. [all data]
Desai, Wilhoit, et al., 1968
Desai, P.D.; Wilhoit, R.C.; Zwolinski, B.J.,
Heat of combustion of resorcinol and enthalpies of isomerization of dihydroxybenzenes,
J. Chem. Eng. Data, 1968, 13, 334-335. [all data]
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Kudchadker S.A., 1979
Kudchadker S.A.,
Ideal gas thermodynamic properties of benzene diols: pyrocatechol, resorcinol, and hydroquinone,
Thermochim. Acta, 1979, 30, 319-326. [all data]
Barker, 1925
Barker, M.F.,
Calorific value and constitution,
J. Phys. Chem., 1925, 29, 1345-1363. [all data]
Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A.,
Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase,
Thermochim. Acta, 1989, 147(2), 261-271. [all data]
Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J.,
Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme,
Z. Natursforsch. 5a, 1950, 101-108. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (3), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Andrews, 1926
Andrews, D.H.,
The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K,
J. Am. Chem. Soc., 1926, 48, 1287-1298. [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]
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]
Bouchoux, Defaye, et al., 2002
Bouchoux, G.; Defaye, D.; McMahon, T.B.; Likholyot, A.; Mo, O.; Yanez, M.,
Structural and energetic aspects of the protonation of phenol, catechol, resorcinol, and hydroquinone,
Chem. Eur. J., 2002, 8, 2900-2909. [all data]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes,
J. Mol. Struct., 1979, 52, 293. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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