Resorcinol
- Formula: C6H6O2
- Molecular weight: 110.1106
- 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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Phase change data
Go To: Top, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
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.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 550. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 549.1 | K | N/A | Krupatkin and Rozhentsova, 1971 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 554.55 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 384. ± 5. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 383.54 | K | N/A | Sabbah and Buluku, 1991 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 382.7 | K | N/A | Ebisuzaki, Askari, et al., 1987 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Ttriple | 382.8 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.25 K; obtained from cooling curve in absence of air; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 18.7 ± 0.31 | kcal/mol | N/A | Verevkin and Kozlova, 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 20.55 ± 0.12 | kcal/mol | C | Sabbah and Buluku, 1991, 2 | ΔHfusion =15.25±0.52 kJ/mol; ALS |
ΔsubH° | 20.6 | kcal/mol | N/A | Sabbah and Buluku, 1991, 2 | DRB |
ΔsubH° | 20.9 ± 0.1 | kcal/mol | C | Sabbah and Buluku, 1991, 2 | AC |
ΔsubH° | 22.2 | kcal/mol | N/A | Desai, Wilhoit, et al., 1968 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
451.2 | 0.021 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.8 | 434. | A | Stephenson and Malanowski, 1987 | Based on data from 419. to 550. K.; AC |
17.8 | 407. | GC | Stephenson and Malanowski, 1987 | Based on data from 392. to 463. K. See also Kundel, Lille, et al., 1975.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
424.7 to 549.7 | 5.51677 | 2687.152 | -62.164 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.4 ± 0.1 | 334. | C | Sabbah and Buluku, 1991, 2 | AC |
22.1 | 353. | GS | Bender, Bieling, et al., 1983 | Based on data from 328. to 379. K.; AC |
22.3 ± 5.0 | 324. to 335. | N/A | Desai, Wilhoit, et al., 1968 | AC |
22.3 | 303. | N/A | Hoyer and Peperle, 1958 | Based on data from 283. to 323. K.; AC |
22.8 ± 0.3 | 329. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.8996 | 381. | N/A | Viikna, Gambino, et al., 1982 | DH |
4.52 | 382.6 | N/A | Bret-Dibat and Lichanot, 1989 | AC |
5.0908 | 382.8 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
5.09 | 382.9 | C | Andrews, Lynn, et al., 1926, 2 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.9 | 381. | Viikna, Gambino, et al., 1982 | DH |
13.3 | 382.8 | Andrews, Lynn, et al., 1926, 2 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.782 | 366.8 | Bret-Dibat and Lichanot, 1989, 2 | CAL |
11.81 | 382.6 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.3274 | 369. | crystaline, II | crystaline, I | Ebisuzaki, Askari, et al., 1987, 2 | DH |
4.9928 | 382.7 | crystaline, I | liquid | Ebisuzaki, Askari, et al., 1987, 2 | DH |
0.2868 | 366.75 | crystaline, II | crystaline, I | Bret-Dibat and Lichanot, 1989 | DH |
4.5172 | 382.55 | crystaline, I | liquid | Bret-Dibat and Lichanot, 1989 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.887 | 369. | crystaline, II, à | crystaline, I, á phase transition | Ebisuzaki, Askari, et al., 1987, 2 | DH |
13.05 | 382.7 | crystaline, I, Fusion of á | liquid, resorcinol | Ebisuzaki, Askari, et al., 1987, 2 | DH |
0.79 | 366.75 | crystaline, II | crystaline, I | Bret-Dibat and Lichanot, 1989 | DH |
14. | 382.55 | crystaline, I | liquid | Bret-Dibat and Lichanot, 1989 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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 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, Phase change 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.
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Krupatkin and Rozhentsova, 1971
Krupatkin, I.L.; Rozhentsova, E.P.,
Some properties of systems with latent liquid immiscibility,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1700. [all data]
Lecat, 1943
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]
Sabbah and Buluku, 1991
Sabbah, R.; Buluku, E.N.L.E.,
Thermodynamic stury of the three isomers of dihydroxybenzene,
Can. J. Chem., 1991, 69, 481. [all data]
Ebisuzaki, Askari, et al., 1987
Ebisuzaki, Y.; Askari, L.H.; Bryan, A.M.,
Phase transitions in resorcinol,
J. Chem. Phys., 1987, 87, 6659-64. [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. [all data]
Verevkin and Kozlova, 2008
Verevkin, Sergey P.; Kozlova, Svetlana A.,
Di-hydroxybenzenes: Catechol, resorcinol, and hydroquinone,
Thermochimica Acta, 2008, 471, 1-2, 33-42, https://doi.org/10.1016/j.tca.2008.02.016
. [all data]
Sabbah and Buluku, 1991, 2
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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
Kundel, Lille, et al., 1975
Kundel, H.; Lille, U.; Kaidas, N.,
Tr. Tallin. Politekh. Inst., 1975, 390, 107. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Bender, Bieling, et al., 1983
Bender, R.; Bieling, V.; Maurer, G.,
The vapour pressures of solids: anthracene, hydroquinone, and resorcinol,
The Journal of Chemical Thermodynamics, 1983, 15, 6, 585-594, https://doi.org/10.1016/0021-9614(83)90058-7
. [all data]
Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W.,
Z. Elektrochem., 1958, 62, 61. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Viikna, Gambino, et al., 1982
Viikna, A.; Gambino, M.; Pouzard, G.; Bros, J.P.,
Determination of partial enthalpies of mixing at infinite dilution of orcinol and resorcinol in water, dibutyl ether and diisopropyl ether,
Calorim. Anal. Therm., 1982, 13, III. [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]
Andrews, Lynn, et al., 1926, 2
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]
Bret-Dibat and Lichanot, 1989, 2
Bret-Dibat, P.; Lichanot, A.,
Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee,
Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0
. [all data]
Ebisuzaki, Askari, et al., 1987, 2
Ebisuzaki, Y.; Askari, L.H.; Bryan, A.M.,
Phase transitions in resorcinol,
J. Chem. Phys., 1987, 87, 6659-6664. [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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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