Resorcinol

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Phase change data

Go To: Top, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, 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
Tboil550.KN/ABuckingham and Donaghy, 1982BS
Tboil549.1KN/AKrupatkin and Rozhentsova, 1971Uncertainty assigned by TRC = 0.4 K; TRC
Tboil554.55KN/ALecat, 1943Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus384. ± 5.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple383.54KN/ASabbah and Buluku, 1991Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple382.7KN/AEbisuzaki, Askari, et al., 1987Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Ttriple382.8KN/AAndrews, Lynn, et al., 1926Uncertainty assigned by TRC = 0.25 K; obtained from cooling curve in absence of air; TRC
Quantity Value Units Method Reference Comment
Δvap18.7 ± 0.31kcal/molN/AVerevkin and Kozlova, 2008AC
Quantity Value Units Method Reference Comment
Δsub20.55 ± 0.12kcal/molCSabbah and Buluku, 1991, 2ΔHfusion =15.25±0.52 kJ/mol; ALS
Δsub20.6kcal/molN/ASabbah and Buluku, 1991, 2DRB
Δsub20.9 ± 0.1kcal/molCSabbah and Buluku, 1991, 2AC
Δsub22.2kcal/molN/ADesai, Wilhoit, et al., 1968DRB

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
451.20.021Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
17.8434.AStephenson and Malanowski, 1987Based on data from 419. to 550. K.; AC
17.8407.GCStephenson and Malanowski, 1987Based 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)

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Temperature (K) A B C Reference Comment
424.7 to 549.75.516772687.152-62.164von Terres, Gebert, et al., 1955Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
20.4 ± 0.1334.CSabbah and Buluku, 1991, 2AC
22.1353.GSBender, Bieling, et al., 1983Based on data from 328. to 379. K.; AC
22.3 ± 5.0324. to 335.N/ADesai, Wilhoit, et al., 1968AC
22.3303.N/AHoyer and Peperle, 1958Based on data from 283. to 323. K.; AC
22.8 ± 0.3329.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
4.8996381.N/AViikna, Gambino, et al., 1982DH
4.52382.6N/ABret-Dibat and Lichanot, 1989AC
5.0908382.8N/AAndrews, Lynn, et al., 1926, 2DH
5.09382.9CAndrews, Lynn, et al., 1926, 2AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
12.9381.Viikna, Gambino, et al., 1982DH
13.3382.8Andrews, Lynn, et al., 1926, 2DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
0.782366.8Bret-Dibat and Lichanot, 1989, 2CAL
11.81382.6

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.3274369.crystaline, IIcrystaline, IEbisuzaki, Askari, et al., 1987, 2DH
4.9928382.7crystaline, IliquidEbisuzaki, Askari, et al., 1987, 2DH
0.2868366.75crystaline, IIcrystaline, IBret-Dibat and Lichanot, 1989DH
4.5172382.55crystaline, IliquidBret-Dibat and Lichanot, 1989DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.887369.crystaline, II, àcrystaline, I, á phase transitionEbisuzaki, Askari, et al., 1987, 2DH
13.05382.7crystaline, I, Fusion of áliquid, resorcinolEbisuzaki, Askari, et al., 1987, 2DH
0.79366.75crystaline, IIcrystaline, IBret-Dibat and Lichanot, 1989DH
14.382.55crystaline, IliquidBret-Dibat and Lichanot, 1989DH

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:


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
8.2×10+66300.XN/A

Gas phase ion energetics data

Go To: Top, Phase change data, Henry's Law data, Gas Chromatography, 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
204.7Bouchoux, Defaye, et al., 2002T = 444-504K; MM

Protonation entropy at 298K

Protonation entropy (cal/mol*K) Reference Comment
-3.6Bouchoux, Defaye, et al., 2002T = 444-504K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.2PEPalmer, Moyes, et al., 1979LLK
8.63PEPalmer, Moyes, et al., 1979Vertical value; LLK

De-protonation reactions

C6H5O2- + Hydrogen cation = Resorcinol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Δr346.6 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr345.2 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr339.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr338.3 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Gas Chromatography

Go To: Top, Phase change data, Henry's Law data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedOV-1180.1379.Radecki and Grzybowski, 1978Chromosorb W HMDS (100-120 mesh); Column length: 2.1 m

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
PackedOV-1011376.Alley and Dykes, 19726. K/min; Tstart: 70. C; Tend: 220. C

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
PackedSE-301368.Grzybowski, Lamparczyk, et al., 1980Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified

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

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Column type Active phase I Reference Comment
CapillarySE-301368.Peterson, 1992Program: not specified

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5MS213.50Chen, Keeran, et al., 200230. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C
CapillaryDB-5MS216.79Chen, Keeran, et al., 200230. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C

Lee's RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes219.64Eckel and Kind, 2003Program: not specified

References

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, 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]

Radecki and Grzybowski, 1978
Radecki, A.; Grzybowski, J., Linear relationship between retention indices and chemical structure of phenols, J. Chromatogr., 1978, 152, 1, 211-213, https://doi.org/10.1016/S0021-9673(00)85352-2 . [all data]

Alley and Dykes, 1972
Alley, B.J.; Dykes, H.W.H., Gas-Liquid Chromatographic Determination of Nitrate Esters,Stabilizers and Plasticizers in Nitrocellulose-Base Propellants, J. Chromatogr., 1972, 71, 1, 23-37, https://doi.org/10.1016/S0021-9673(01)85687-9 . [all data]

Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A., Relationship between the retention indices of phenols on polar and non-polar stationary phases, J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0 . [all data]

Peterson, 1992
Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W., Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]

Eckel and Kind, 2003
Eckel, W.P.; Kind, T., Use of boiling point-Lee retention index correlation for rapid review of gas chromatography-mass spectrometry data, Anal. Chim. Acta., 2003, 494, 1-2, 235-243, https://doi.org/10.1016/j.aca.2003.08.003 . [all data]


Notes

Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, References