Ethanamine, N-ethyl-
- Formula: C4H11N
- Molecular weight: 73.1368
- IUPAC Standard InChIKey: HPNMFZURTQLUMO-UHFFFAOYSA-N
- CAS Registry Number: 109-89-7
- 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: Diethylamine; N,N-Diethylamine; (C2H5)2NH; DEA; Diaethylamin; Diethamine; Dietilamina; Dwuetyloamina; UN 1154; N-Ethylethanamine
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -23.9 | kcal/mol | N/A | Lemoult, 1907 | Value computed using ΔfHliquid° value of -131 kj/mol from Lemoult, 1907 and ΔvapH° value of 31.18±0.06 kj/mol from missing citation. |
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 | -31.2 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -725.5 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
42.57 | 298.15 | Costas and Patterson, 1985 | T = 283.15, 298.15, 313.15 K.; DH |
42.57 | 298.15 | Costas and Patterson, 1985, 2 | DH |
25.41 | 290. | Kurnakov and Voskresenskaya, 1936 | 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 | 328.7 ± 0.8 | K | AVG | N/A | Average of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 223.15 | K | N/A | Pohland and Mehl, 1933 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 225.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 223.15 | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 223.15 | K | N/A | Berthoud, 1917 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 498. ± 3. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 36.99 | atm | N/A | Mandlekar, Kay, et al., 1985 | Uncertainty assigned by TRC = 0.987 atm; TRC |
Pc | 37.09 | atm | N/A | Kay and Young, 1976 | Uncertainty assigned by TRC = 0.15 atm; TRC |
Pc | 37.09 | atm | N/A | Kay and Young, 1976, 2 | Uncertainty assigned by TRC = 0.15 atm; TRC |
Pc | 36.9897 | atm | N/A | Kreglewski and Kay, 1969 | Uncertainty assigned by TRC = 0.2041 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.32 | mol/l | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.522 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.48 ± 0.02 | kcal/mol | C | Majer, Svoboda, et al., 1979 | AC |
ΔvapH° | 7.82 ± 0.05 | kcal/mol | I | Franks and Watson, 1969 | Based on data from 273. to 333. K.; AC |
ΔvapH° | 7.46 ± 0.02 | kcal/mol | C | Wadsö, Heikkilä, et al., 1969 | AC |
ΔvapH° | 7.45 ± 0.01 | kcal/mol | C | Wadso, 1969 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.946 | 328.7 | N/A | Majer and Svoboda, 1985 | |
7.46 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 302. to 328. K.; AC |
7.27 | 340. | A | Stephenson and Malanowski, 1987 | Based on data from 325. to 437. K.; AC |
6.79 | 446. | A | Stephenson and Malanowski, 1987 | Based on data from 431. to 496. K.; AC |
7.22 ± 0.02 | 313. | C | Majer, Svoboda, et al., 1979 | AC |
6.96 ± 0.02 | 328. | C | Majer, Svoboda, et al., 1979 | AC |
6.69 ± 0.02 | 343. | C | Majer, Svoboda, et al., 1979 | AC |
7.60 | 307. | N/A | Kilian and Bittrich, 1965 | Based on data from 292. to 313. K. See also Boublik, Fried, et al., 1984.; AC |
7.53 | 319. | N/A | Bittrich and Kauer, 1962 | Based on data from 304. to 323. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 343. | 12.29 | 0.3266 | 496.5 | Majer and Svoboda, 1985 |
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 |
---|---|---|---|---|---|
304.60 to 333.73 | 2.85622 | 559.071 | -132.974 | Bittrich and Kauer, 1962, 2 | Coefficents calculated by NIST from author's data. |
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:
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: C3H9Sn+ + C4H11N = (C3H9Sn+ • C4H11N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 46.4 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 33. | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
29.1 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
By formula: C8H20N2S2 + 2C4H12ClN = Cl2S2 + 4C4H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 87.30 ± 0.70 | kcal/mol | Cm | Claydon and Mortimer, 1962 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 88.0 ± 0.7 kcal/mol; ALS |
By formula: C8H20N2O2S + 2C4H12ClN = 4C4H11N + Cl2O2S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 130.0 ± 1.7 | kcal/mol | Cm | Claydon and Mortimer, 1962 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 129.8 ± 1.7 kcal/mol; ALS |
By formula: C8H20N2OS + 2C4H12ClN = 4C4H11N + Cl2OS
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 90.7 ± 1.0 | kcal/mol | Cm | Claydon and Mortimer, 1962 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 93.9 ± 1.0 kcal/mol; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C4H11N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 227.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 219.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.9 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
8.51 | PE | Al-Joboury and Turner, 1964 | RDSH |
8.01 ± 0.01 | PI | Watanabe and Mottl, 1957 | RDSH |
8.68 | PE | Gibbins, Lappert, et al., 1975 | Vertical value; LLK |
8.630 | PE | Aue, Webb, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 14.64 | ? | EI | Collin and Franskin, 1966 | RDSH |
CH3+ | 15.4 | C2H5NHCH2 | EI | SenSharma and Franklin, 1973 | LLK |
CH4N+ | 13.10 ± 0.10 | C2H4+CH3 | EI | Collin and Franskin, 1966 | RDSH |
C2H3+ | 15.35 | ? | EI | Collin and Franskin, 1966 | RDSH |
C2H5+ | 14.85 | ? | EI | Collin and Franskin, 1966 | RDSH |
C2H6N+ | 11.42 ± 0.05 | C2H5 | EI | Solka and Russell, 1974 | LLK |
C2H6N+ | 13.65 ± 0.08 | ? | EI | Collin and Franskin, 1966 | RDSH |
C3H8N+ | 8.92 | CH3 | EI | Lossing, Lam, et al., 1981 | LLK |
C3H8N+ | 9.55 ± 0.10 | CH3 | EI | Collin and Franskin, 1966 | RDSH |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C3H9Sn+ + C4H11N = (C3H9Sn+ • C4H11N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 46.4 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 33. | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
29.1 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lemoult, 1907
Lemoult, M.P.,
Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques,
Ann. Chim. Phys., 1907, 12, 395-432. [all data]
Costas and Patterson, 1985
Costas, M.; Patterson, D.,
Heat capacities of water + organic-solvent mixtures, J. Chem. Soc.,
Faraday Trans. 1, 1985, 81, 2381-2398. [all data]
Costas and Patterson, 1985, 2
Costas, M.; Patterson, D.,
Self-association of alcohols in inert solvents, J. Chem. Soc.,
Faraday Trans. 1, 1985, 81, 635-654. [all data]
Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K.,
Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR,
Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]
Pohland and Mehl, 1933
Pohland, E.; Mehl, W.,
Physical Properties of Ethylamine.,
Z. Phys. Chem., Abt. A, 1933, 164, 48. [all data]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]
Timmermans, 1921
Timmermans, J.,
The Freezing Points of Organic Substances IV. New Exp. Determinations,
Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]
Berthoud, 1917
Berthoud, A.,
Determination of Critical Temperatures and Pressures of Amines and Alkyl Chlorides,
J. Chim. Phys. Phys.-Chim. Biol., 1917, 15, 3. [all data]
Mandlekar, Kay, et al., 1985
Mandlekar, A.V.; Kay, W.B.; Smith, R.L.; Teja, A.S.,
Phase equilibria in the n-hexane + diethylamine system,
Fluid Phase Equilib., 1985, 23, 79. [all data]
Kay and Young, 1976
Kay, W.B.; Young, C.L.,
Gas-liquid critical properties. Diethylamine-methanol system,
Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1976, No. 1, 74. [all data]
Kay and Young, 1976, 2
Kay, W.B.; Young, C.L.,
Gas-liquid critical properties. Diethylamine, 2-butanone (methylethyl ketone) system,
Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1976, No. 1, 76. [all data]
Kreglewski and Kay, 1969
Kreglewski, A.; Kay, W.B.,
The Critical Constants of Conformal Mixtures,
J. Phys. Chem., 1969, 73, 3359. [all data]
Herz and Neukirch, 1923
Herz, W.; Neukirch, E.,
On Knowldge of the Critical State,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Koubek, Josef; Pick, Jirí,
Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies for a group of amines,
Collect. Czech. Chem. Commun., 1979, 44, 12, 3521-3528, https://doi.org/10.1135/cccc19793521
. [all data]
Franks and Watson, 1969
Franks, F.; Watson, B.,
Calorimetric study of dilute aqueous solutions of dialkylamines: hydration of alkyl groups,
Trans. Faraday Soc., 1969, 65, 2339, https://doi.org/10.1039/tf9696502339
. [all data]
Wadsö, Heikkilä, et al., 1969
Wadsö, Ingemar; Heikkilä, Jussi; Beagley, B.; Aalto, Tarja; Werner, Per-Erik; Junggren, Ulf; Lamm, Bo; Samuelsson, Benny,
Enthalpies of Vaporization of Organic Compounds. III. Amines.,
Acta Chem. Scand., 1969, 23, 2061-2064, https://doi.org/10.3891/acta.chem.scand.23-2061
. [all data]
Wadso, 1969
Wadso, I.,
Enthalpies of vaporization of organic compounds,
Acta Chem. Scand., 1969, 23, 2061. [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]
Kilian and Bittrich, 1965
Kilian, H.; Bittrich, H.J.,
Z. Phys. Chem., 1965, 230, 383. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Bittrich and Kauer, 1962
Bittrich, H.-J.; Kauer, E.,
Z. Phys. Chem. [Frankfurt am Main], 1962, 219, 224. [all data]
Bittrich and Kauer, 1962, 2
Bittrich, H.J.; Kauer, E.,
Zur Thermodynamik des Systems Diathylamin-Triathylamin. I. Das Flussigkeits-Dampf-Gleichgewicht,
Z. Phys. Chem. (Frankfurt/Main), 1962, 219, 224-238. [all data]
Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E.,
A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase,
Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]
Claydon and Mortimer, 1962
Claydon, A.P.; Mortimer, C.T.,
Heats of formation and bond energies. Part VIII. Diethylaminotrimethylsilane, NN'-dithiodiethylamine, NN'-thionylbisdiethylamine, and NN'-sulphurylbisdiethylamine,
J. Chem. Soc., 1962, 3212-3216. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [all data]
Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials,
J. Chem. Soc., 1964, 4434. [all data]
Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R.,
Ionization potentials of ammonia and some amines,
J. Chem. Phys., 1957, 26, 1773. [all data]
Gibbins, Lappert, et al., 1975
Gibbins, S.G.; Lappert, M.F.; Pedley, J.B.; Sharp, G.J.,
Bonding studies of transition-metal complexes. Part II. Helium-I photoelectron spectra of homoleptic d0, d1, and d10 tetrakis(dialkylamides) of transition group 4B metals tungsten hexakis(dimethylamide),
J. Chem. Soc. Dalton Trans., 1975, 72. [all data]
Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects,
J. Am. Chem. Soc., 1975, 97, 4137. [all data]
Collin and Franskin, 1966
Collin, J.E.; Franskin, M.J.,
Ionisation, dissociation et rearrangements intramoleculaires dans les amines aliphatiques soumises a l'impact electronique. Cas de la diethylamine et de la diethylamine-Nd,
Bull. Soc. Roy. Sci. Liege, 1966, 35, 285. [all data]
SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L.,
Heat of formation of free radicals by mass spectrometry,
J. Am. Chem. Soc., 1973, 95, 6562. [all data]
Solka and Russell, 1974
Solka, B.H.; Russell, M.E.,
Energetics of formation of some structural isomers of gaseous C2H5O+ C2H6N+ ions,
J. Phys. Chem., 1974, 78, 1268. [all data]
Lossing, Lam, et al., 1981
Lossing, F.P.; Lam, Y.-T.; Maccoll, A.,
Gas phase heats of formation of alkyl immonium ions,
Can. J. Chem., 1981, 59, 2228. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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 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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