Propanoic acid, 2,2-dimethyl-
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChIKey: IUGYQRQAERSCNH-UHFFFAOYSA-N
- CAS Registry Number: 75-98-9
- 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: Pivalic acid; α,α-Dimethylpropionic acid; tert-Pentanoic acid; Neopentanoic acid; Trimethylacetic acid; 2,2-Dimethylpropanoic acid; 2,2-Dimethylpropionic acid; tert-C4H9COOH; Acetic acid, trimethyl-; Propionic acid, 2,2-dimethyl-; Kyselina 2,2-dimethylpropionova; Kyselina pivalova; NSC 65449; Neovaleric acid; Versatic 5
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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°solid | -564.5 ± 5.9 | kJ/mol | Ccb | Hancock, Watson, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -565. kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2832.1 ± 5.9 | kJ/mol | Ccb | Hancock, Watson, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2830. kJ/mol; Corresponding ΔfHºsolid = -564.55 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
192.2 | 298.15 | Singh and Glicksman, 1990 | T = 295 to 319 K. Cp(c) = 13.38 + 0.1092T cal/mol*K (295 to 300 K). Cp value calculated from equation. Cp(liq) = 16.19 + 0.1042T cal/mol*K.; DH |
178. | 298.15 | Konicek and Wadso, 1971 | 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 436. ± 3. | K | AVG | N/A | Average of 27 out of 32 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 308. ± 3. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 73.2 ± 3.0 | kJ/mol | V | Kruif and Oonk, 1979 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
57.6 ± 0.2 | 320. | EB | Steele, Chirico, et al., 2002 | Based on data from 344. to 472. K.; AC |
54.4 ± 0.2 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 344. to 472. K.; AC |
50.9 ± 0.2 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 344. to 472. K.; AC |
47.0 ± 0.4 | 440. | EB | Steele, Chirico, et al., 2002 | Based on data from 344. to 472. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
62.3 | 291. | GS | Verevkin, 2000 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.3 | 309.1 | Steele, Chirico, et al., 2002 | AC |
2.27 | 309.1 | Singh and Glicksman, 1990 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
8.760 | 281. | crystaline, II | crystaline, I | Murrill and Breed, 1970 | DH |
2.479 | 307. | crystaline, I | liquid | Murrill and Breed, 1970 | DH |
8.184 | 278.3 | crystaline, II | crystaline, I | Singh and Glicksman, 1990 | DH |
2.268 | 309.085 | crystaline, I | liquid | Singh and Glicksman, 1990 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
31.4 | 281. | crystaline, II | crystaline, I | Murrill and Breed, 1970 | DH |
7.9 | 307. | crystaline, I | liquid | Murrill and Breed, 1970 | DH |
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
C5H9O2- + =
By formula: C5H9O2- + H+ = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1442. ± 8.8 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 1443. ± 8.8 | kJ/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1413. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 1414. ± 8.4 | kJ/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: I- + C5H10O2 = (I- • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64.4 ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.8 | J/mol*K | PHPMS | Caldwell and Kebarle, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 37. ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B |
By formula: C10H18O3 + H2O = 2C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -63.26 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; 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 |
---|---|---|---|
350. | M | N/A |
Gas phase ion energetics 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.08 | EI | Holmes, Fingas, et al., 1981 | LLK |
10.3 | PE | Green and Hayes, 1975 | Vertical value; LLK |
De-protonation reactions
C5H9O2- + =
By formula: C5H9O2- + H+ = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1442. ± 8.8 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 1443. ± 8.8 | kJ/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1413. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 1414. ± 8.4 | kJ/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
Ion clustering 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
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: I- + C5H10O2 = (I- • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64.4 ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.8 | J/mol*K | PHPMS | Caldwell and Kebarle, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 37. ± 4.2 | kJ/mol | TDAs | Caldwell and Kebarle, 1984 | gas phase; B |
IR 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Download spectrum in JCAMP-DX format.
Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Japan AIST/NIMC Database- Spectrum MS-NW-1453 |
NIST MS number | 229708 |
Gas Chromatography
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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
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1527. | Chung, Fung, et al., 2005 | 60. m/0.25 mm/0.25 μm, 35. C @ 5. min, 6. K/min, 195. C @ 60. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 864. | Zhao, Li, et al., 2008 | 30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min) |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTX-Wax | 1563. | Prososki, Etzel, et al., 2007 | 30. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 10. K/min, 220. C @ 10. min |
Capillary | TC-Wax | 1568. | Suhardi, Suzuki, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 3. K/min, 230. C @ 10. min |
Capillary | DB-Wax | 1579. | Sekiwa, Kubota, et al., 1997 | He, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 180. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SOLGel-Wax | 1586. | Johanningsmeier and McFeeters, 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min) |
Capillary | SOLGel-Wax | 1579. | Johanningsmeier and McFeeters, 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hancock, Watson, et al., 1954
Hancock, C.K.; Watson, G.M.; Gilby, R.F.,
Heats of combustion of five-carbon fatty acids and their methyl and ethyl esters,
J. Phys. Chem., 1954, 58, 127-129. [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]
Singh and Glicksman, 1990
Singh, N.B.; Glicksman, M.E.,
Physical properties of ultra-pure pivalic acid,
Thermochim. Acta, 1990, 159, 93-99. [all data]
Konicek and Wadso, 1971
Konicek, J.; Wadso, I.,
Thermochemical properties of some carboxylic acids, amines and N-substituted amides in aqueous solution,
Acta Chem. Scand., 1971, 25, 1541-1551. [all data]
Kruif and Oonk, 1979
Kruif, C.G.; Oonk, H.A.J.,
Enthalpies of vaporization and vapour pressures of seven aliphatic carboxylic acids,
J. Chem. Thermodyn., 1979, 11, 287-290. [all data]
Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for trans -Methyl Cinnamate, α-Methyl Cinnamaldehyde, Methyl Methacrylate, 1-Nonyne, Trimethylacetic Acid, Trimethylacetic Anhydride, and Ethyl Trimethyl Acetate,
J. Chem. Eng. Data, 2002, 47, 4, 700-714, https://doi.org/10.1021/je010086r
. [all data]
Verevkin, 2000
Verevkin, S.P.,
Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties,
J. Chem. Eng. Data, 2000, 45, 5, 953-960, https://doi.org/10.1021/je990282m
. [all data]
Murrill and Breed, 1970
Murrill, E.; Breed, L.,
Solid-solid phase transitions determined by differential scanning calorimetry,
Thermochim. Acta, 1970, 1, 239-246. [all data]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
Jinfeng, Topsom, et al., 1988
Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S.,
Acidities of Substituted Acetic Acids,
J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X
. [all data]
Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P.,
Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements,
J. Am. Chem. Soc., 1984, 106, 967. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations,
Can. J. Chem., 1981, 59, 80. [all data]
Green and Hayes, 1975
Green, J.C.; Hayes, A.J.,
Ionization energies of an Mo-Mo quadruple bond; a He(I) photoelectron study of some molybdenum-dycarboxylate dimers,
Chem. Phys. Lett., 1975, 31, 306. [all data]
Chung, Fung, et al., 2005
Chung, H.Y.; Fung, P.K.; Kim, J.-S.,
Aroma impact components in commercial plain sufu,
J. Agric. Food Chem., 2005, 53, 5, 1684-1691, https://doi.org/10.1021/jf048617d
. [all data]
Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G.,
EXtraction, preparation and identification of volatile compounds in Changyu XO brandy,
Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0
. [all data]
Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A.,
Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder,
J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7
. [all data]
Suhardi, Suzuki, et al., 2002
Suhardi, S.; Suzuki, M.; Yoshida, K.; Muto, T.; Fujita, A.; Watanbe, N.,
Changes in the volatile compounds and in the chemical and physical properties of snake fruit (Salacca edulis Reinw) Cv. Pondoh during maturation,
J. Agric. Food Chem., 2002, 50, 26, 7627-7633, https://doi.org/10.1021/jf020620e
. [all data]
Sekiwa, Kubota, et al., 1997
Sekiwa, Y.; Kubota, K.; Kobayashi, A.,
Characteristic flavor components in the brew of cooked clam (Meretrix lusoria) and the effect of storage on flavor formation,
J. Agric. Food Chem., 1997, 45, 3, 826-830, https://doi.org/10.1021/jf960433e
. [all data]
Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F.,
Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS),
J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point 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 ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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