Acetophenone
- Formula: C8H8O
- Molecular weight: 120.1485
- IUPAC Standard InChIKey: KWOLFJPFCHCOCG-UHFFFAOYSA-N
- CAS Registry Number: 98-86-2
- 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. - Isotopologues:
- Other names: Ethanone, 1-phenyl-; Acetophenon; Benzoyl methide; Hypnon; Hypnone; Methyl phenyl ketone; Phenyl methyl ketone; 1-Phenylethanone; Acetylbenzene; 1-Phenyl-1-ethanone; Ketone, methyl phenyl-; USAF EK-496; Acetofenon; Benzene, acetyl-; Dymex; Rcra waste number U004; Acetylbenzol; NSC 7635; Phenylethanone; 1-phenylethanone (acetophenone)
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -86.7 ± 1.7 | kJ/mol | N/A | Cox and Pilcher, 1970 | Review; Heat of formation from Colomina, Latorre, et al., 1961; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 372.88 | J/mol*K | N/A | Stull D.R., 1969 | GT |
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°liquid | -142.5 ± 1.0 | kJ/mol | Ccb | Colomina, Latorre, et al., 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -142.5 ± 1.0 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4140. | kJ/mol | Ccb | Seno, Tsuchiya, et al., 1975 | Corresponding ΔfHºliquid = -151. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -4148.9 ± 0.88 | kJ/mol | Ccb | Colomina, Latorre, et al., 1961 | Corresponding ΔfHºliquid = -142.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -4136. | kJ/mol | Ccb | Guinchant, 1918 | Corresponding ΔfHºliquid = -156. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
227.6 | 303.2 | Phillip, 1939 | 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 475. ± 1. | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 293.0 ± 0.6 | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 713. | K | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 2. K; TRC |
Tc | 709.6 | K | N/A | Teja and Rosenthal, 1991 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 709.5 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 44.00 | bar | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 1.50 bar; from extraploation of obs. vapor pressures to Tc; TRC |
Pc | 40.10 | bar | N/A | Teja and Rosenthal, 1991 | Uncertainty assigned by TRC = 0.30 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.62 | mol/l | N/A | Steele, Chirico, et al., 1996 | Uncertainty assigned by TRC = 0.10 mol/l; TRC |
ρc | 2.59 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.05 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 55.4 ± 0.4 | kJ/mol | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
ΔvapH° | 53.4 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
ΔvapH° | 52.7 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
ΔvapH° | 57.9 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
ΔvapH° | 55.9 ± 1.3 | kJ/mol | V | Cox and Pilcher, 1970 | Review; Heat of formation from Colomina, Latorre, et al., 1961; ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
340. | 0.007 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
52.6 ± 0.4 | 340. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
50.1 ± 0.3 | 380. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
47.5 ± 0.3 | 420. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
45.0 ± 0.4 | 460. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
42.2 ± 0.4 | 500. | EB | Steele, Chirico, et al., 1996, 2 | Based on data from 360. to 520. K.; AC |
49.7 | 390. | A | Stephenson and Malanowski, 1987 | Based on data from 375. to 603. K.; AC |
41.9 | 398. | GS,EB | Collerson, Counsell, et al., 1965 | Based on data from 383. to 437. K.; AC |
51.2 | 325. | N/A | Stull, 1947 | Based on data from 310. to 476. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
310.3 to 475.6 | 4.64896 | 2006.397 | -43.472 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
16.65 | 292.7 | Louguinine and Dupont, 1911 | See also Sedláková, Malijevská, et al., 2006.; 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
By formula: Br- + C8H8O = (Br- • C8H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 23. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
23. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
C8H7O- + =
By formula: C8H7O- + H+ = C8H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1512. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1515. ± 11. | kJ/mol | D-EA | Zimmerman, Reed, et al., 1977 | gas phase; B |
ΔrH° | 1516. ± 11. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1483. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1487. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: C8H9O + C8H8O = (C8H9O • C8H8O)
Bond type: Hydrogen bonds of the type OH-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 112. | kJ/mol | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 114. | J/mol*K | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; M |
By formula: Cl- + C8H8O = (Cl- • C8H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 39.7 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
30. | 421. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
By formula: C7H6O + C8H8O = H2O + C15H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -65.0 ± 1.9 | kJ/mol | Cm | Hao, Chang, et al., 1985 | liquid phase; solvent: Aqueous NaOH; ALS |
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) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
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)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
110. | 6000. | M | N/A |
94. | V | N/A |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- LIQUID (NEAT); PERKIN-ELMER 180 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (LESS THAN 10% IN CCl4 FOR 4000-1330 CM-1, LESS THAN 10% IN CS2 FOR 1330-600 CM-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- VAPOR (12 MICROLITER AT 150 C); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2-3 CM-1 cm-1 resolution
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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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 | Chemical Concepts |
NIST MS number | 223435 |
UV/Visible spectrum
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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Clark and Tinoco, 1965 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 7310 |
Instrument | n.i.g. |
Melting point | 20 |
Boiling point | 202 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Colomina, Latorre, et al., 1961
Colomina, M.; Latorre, C.; Perez-Ossorio, R.,
Heats of combustion of five alkyl phenyl ketones,
Pure & Appl. Chem., 1961, 2, 133-135. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Seno, Tsuchiya, et al., 1975
Seno, M.; Tsuchiya, S.; Kise, H.; Asahara, T.,
Studies on bond character in phosphorus ylides by combustion heat and x-ray photoelectron spectroscopy,
Bull. Chem. Soc. Jpn., 1975, 48, 2001-2005. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [all data]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor pressure of acetophenone, (+-)-1,2-butanediol, (+-)-1,3-butanediol, diethylene glycol monopropyl ether, 1,3-dimethyladamantane, 2-ethoxyethyl acetate, ethyl octyl sufide, and pentyl acetate,
J. Chem. Eng. Data, 1996, 41, 1255-68. [all data]
Teja and Rosenthal, 1991
Teja, A.S.; Rosenthal, D.J.,
The critical pressures and temperatures of ten substances using a low residence time flow apparatus
in Experimental Results for Phase Equilibria and Pure Component Properties, DIPPR DATA Series No. 1, 1991. [all data]
Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J.,
The critical properties of thermally stable and unstable fluids. I. 1985 results,
AIChE Symp. Ser., 1990, 86, 279, 115-21. [all data]
Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure of Acetophenone, (±)-1,2-Butanediol, (±)-1,3-Butanediol, Diethylene Glycol Monopropyl Ether, 1,3-Dimethyladamantane, 2-Ethoxyethyl Acetate, Ethyl Octyl Sulfide, and Pentyl Acetate,
J. Chem. Eng. Data, 1996, 41, 6, 1255-1268, https://doi.org/10.1021/je9601117
. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 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]
Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S.,
677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers,
J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Louguinine and Dupont, 1911
Louguinine, W.; Dupont, G.,
Bull. Soc. Chim. Fr., 1911, 9, 219. [all data]
Sedláková, Malijevská, et al., 2006
Sedláková, Zuzana; Malijevská, Ivona; Rehák, Karel; Vrbka, Pavel,
Solid-Liquid and Liquid-Liquid Equilibrium in the Formamide-Acetophenone System,
Collect. Czech. Chem. Commun., 2006, 71, 9, 1350-1358, https://doi.org/10.1135/cccc20061350
. [all data]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I.,
Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals,
J. Am. Chem. Soc., 1977, 99, 7203. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W.,
Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range,
J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012
. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Hao, Chang, et al., 1985
Hao, J.; Chang, J.; Wang, K.; Liu, Y.; Zhong, G.,
Heat of reaction of chalcone by calorimetric measurement,
Huaxue Tongbao, 1985, 15-16. [all data]
Clark and Tinoco, 1965
Clark, L.B.; Tinoco, I., Jr.,
Correlations in the ultraviolet spectra of the purine and pyrimidine bases,
J. Am. Chem. Soc., 1965, 87, 1, 11-15. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°gas Entropy of gas at standard conditions T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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