Formamide, N,N-dimethyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N
- CAS Registry Number: 68-12-2
- 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. - Other names: Dimethylformamide; DMF; DMF (amide); DMFA; N-Formyldimethylamine; N,N-Dimethylformamide; HCON(CH3)2; Formyldimethylamine; Dimethylforamide; Dimethylformamid; Dimetilformamide; Dwumetyloformamid; N,N-Dimethylmethanamide; NSC-5356; U-4224; Dimethylamid kyseliny mravenci; Dimetylformamidu; NCI-C60913; UN 2265; DMF (dimethylformamide); N,N-Dimethylformaldehyde
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Phase change data
Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tboil | 426. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 212.7 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 649.6 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.82 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.08 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.2 ± 0.1 | kcal/mol | CGC | Panneerselvam, Antony, et al., 2009 | Based on data from 463. to 513. K.; AC |
ΔvapH° | 11.2 | kcal/mol | A | Barone, Castronuovo, et al., 1985 | See also Majer and Svoboda, 1985.; AC |
ΔvapH° | 11.37 | kcal/mol | E | Geller, 1961 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.3 | 361. | N/A | Muñoz, Montón, et al., 2005 | Based on data from 346. to 425. K.; AC |
9.99 | 392. | N/A | Blanco, Beltrán, et al., 1997 | Based on data from 377. to 426. K.; AC |
10.4 | 353. | N/A | Marzal, Gabaldon, et al., 1995 | Based on data from 338. to 425. K.; AC |
11.8 | 316. | A | Stephenson and Malanowski, 1987 | Based on data from 301. to 426. K.; AC |
10.2 | 370. | N/A | Bludilina, Baev, et al., 1979 | Based on data from 318. to 423. K.; AC |
13.6 | 346. | N/A | Myasinkova, Schmelev, et al., 1974 | Based on data from 331. to 425. K. See also Boublik, Fried, et al., 1984.; AC |
11.2 | 318. | N/A | Gopal and Rizvi, 1968 | Based on data from 303. to 363. K.; 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 |
---|---|---|---|---|---|
303. to 363. | 3.92497 | 1337.716 | -82.648 | Gopal and Rizvi, 1968, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.139 | 212.85 | N/A | Karyakin, Rabinovich, et al., 1978 | DH |
2.14 | 212.9 | AC | Smirnova, Tsvetkova, et al., 2007 | AC |
2.14 | 212.9 | N/A | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.99 | 212.85 | Karyakin, Rabinovich, et al., 1978 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C3H7NO+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.13 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 212.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 204.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.01362 | Desfrancois, Periquet, et al., 1999 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.45 ± 0.05 | EI | Baldwin, Loudon, et al., 1977 | LLK |
9.14 | PE | Brundle, Turner, et al., 1969 | RDSH |
9.12 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.14 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.25 | PE | Henriksen, Isaksson, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 14.50 | ? | EI | Loudon and Webb, 1977 | LLK |
CHO+ | 14.3 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C2H6N+ | 11.60 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H6N+ | 11.6 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C3H6NO+ | 11.35 | ? | EI | Loudon and Webb, 1977 | LLK |
De-protonation reactions
C3H6NO- + =
By formula: C3H6NO- + H+ = C3H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.1 ± 4.1 | kcal/mol | G+TS | DePuy, Grabowski, et al., 1985 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 392.0 ± 4.0 | kcal/mol | IMRB | DePuy, Grabowski, et al., 1985 | gas phase; B |
Ion clustering data
Go To: Top, Phase change 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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: C6F4O2- + C3H7NO = (C6F4O2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 2.7 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
2.7 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4FNO2- + C3H7NO = (C6H4FNO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 5.9 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.9 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4FNO2- + C3H7NO = (C6H4FNO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 5.9 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.9 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4FNO2- + C3H7NO = (C6H4FNO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 5.6 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.6 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4N2O4- + C3H7NO = (C6H4N2O4- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 2.5 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
2.5 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4N2O4- + C3H7NO = (C6H4N2O4- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.5 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.5 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H4O2- + C3H7NO = (C6H4O2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.3 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.3 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C6H5NO2- + C3H7NO = (C6H5NO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 6.2 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
6.2 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
C7H4F3NO2- + = (C7H4F3NO2- • )
By formula: C7H4F3NO2- + C3H7NO = (C7H4F3NO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.8 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.8 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H4N2O2- + C3H7NO = (C7H4N2O2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.5 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.5 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H4N2O2- + C3H7NO = (C7H4N2O2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 4.8 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
4.8 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H4N2O2- + C3H7NO = (C7H4N2O2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 3.9 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
3.9 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H7NO2- + C3H7NO = (C7H7NO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 6.2 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
6.2 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H7NO2- + C3H7NO = (C7H7NO2- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 6.3 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
6.3 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H7NO3- + C3H7NO = (C7H7NO3- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 5.9 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.9 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
5.9 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: C7H7NO3- + C3H7NO = (C7H7NO3- • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 6.2 ± 1.6 | kcal/mol | IMRE | Chowdhury, Grimsrud, et al., 1987 | gas phase; Free energy affinity at 70°C.; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
6.2 | 343. | PHPMS | Chowdhury, 1987 | gas phase; M |
By formula: K+ + C3H7NO = (K+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 29.5 | kcal/mol | CIDT | Klassen, Anderson, et al., 1996 | RCD |
ΔrH° | 31. | kcal/mol | HPMS | Sunner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26. | cal/mol*K | HPMS | Sunner, 1984 | gas phase; M |
By formula: (K+ • C3H7NO) + C3H7NO = (K+ • 2C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21. | kcal/mol | HPMS | Sunner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 20. | cal/mol*K | HPMS | Sunner, 1984 | gas phase; M |
By formula: (K+ • 2C3H7NO) + C3H7NO = (K+ • 3C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15. | kcal/mol | HPMS | Sunner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 18. | cal/mol*K | HPMS | Sunner, 1984 | gas phase; M |
By formula: (K+ • 3C3H7NO) + C3H7NO = (K+ • 4C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13. | kcal/mol | HPMS | Sunner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 24. | cal/mol*K | HPMS | Sunner, 1984 | gas phase; M |
By formula: Li+ + C3H7NO = (Li+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: Na+ + C3H7NO = (Na+ • C3H7NO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.4 ± 0.9 | kcal/mol | CIDT | Armentrout and Rodgers, 2000 | See 96KLA/AND?; RCD |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
30.1 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
References
Go To: Top, Phase change 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.
Dreisbach, 1955
Dreisbach, R.R.,
Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]
Teja and Anselme, 1990
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The critical properties of thermally stable and unstable fluids. I. 1985 results,
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Panneerselvam, K.; Antony, M.P.; Srinivasan, T.G.; Vasudeva Rao, P.R.,
Enthalpies of vaporization of N,N-dialkyl monamides at 298.15K,
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Barone, Castronuovo, et al., 1985
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Enthalpies of vaporization of seven alkylamides,
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Majer and Svoboda, 1985
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Geller, 1961
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Properties of the dimethylformamide water system. I. Thermochemical properties,
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Phase equilibria in the systems isobutyl alcohol+N,N-dimethylformamide, isobutyl acetate+N,N-dimethylformamide and isobutyl alcohol+isobutyl acetate+N,N-dimethylformamide at 101.3kPa,
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Bludilina, Baev, et al., 1979
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Zh. Fiz. Khim., 1979, 53, 1052. [all data]
Myasinkova, Schmelev, et al., 1974
Myasinkova, L.F.; Schmelev, V.A.; Vaisman, I.L.; Bushinskii, V.I.; Novokhatka, D.A.,
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Boublik, T.; Fried, V.; Hala, E.,
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Gopal, R.; Rizvi, S.A.,
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Gopal, R.; Rizvi, S.A.,
Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures,
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Thermodynamic properties of N,N-dimethylformamide and N,N-dimethylacetamide,
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Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Desfrancois, Periquet, et al., 1999
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Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy 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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