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Propanoic acid, 2,2-dimethyl-

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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
Deltafsolid-564.5 ± 5.9kJ/molCcbHancock, Watson, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -565. kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-2832.1 ± 5.9kJ/molCcbHancock, Watson, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -2830. kJ/mol; Corresponding «DELTA»fsolid = -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
192.2298.15Singh and Glicksman, 1990T = 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
178.298.15Konicek and Wadso, 1971DH

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
Tboil436. ± 3.KAVGN/AAverage of 27 out of 32 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus308. ± 3.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub73.2 ± 3.0kJ/molVKruif and Oonk, 1979ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
57.6 ± 0.2320.EBSteele, Chirico, et al., 2002Based on data from 344. - 472. K.; AC
54.4 ± 0.2360.EBSteele, Chirico, et al., 2002Based on data from 344. - 472. K.; AC
50.9 ± 0.2400.EBSteele, Chirico, et al., 2002Based on data from 344. - 472. K.; AC
47.0 ± 0.4440.EBSteele, Chirico, et al., 2002Based on data from 344. - 472. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
62.3291.GSVerevkin, 2000AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
2.3309.1Steele, Chirico, et al., 2002AC
2.27309.1Singh and Glicksman, 1990AC

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
8.760281.crystaline, IIcrystaline, IMurrill and Breed, 1970DH
2.479307.crystaline, IliquidMurrill and Breed, 1970DH
8.184278.3crystaline, IIcrystaline, ISingh and Glicksman, 1990DH
2.268309.085crystaline, IliquidSingh and Glicksman, 1990DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
31.4281.crystaline, IIcrystaline, IMurrill and Breed, 1970DH
7.9307.crystaline, IliquidMurrill and Breed, 1970DH

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:


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- + Hydrogen cation = Propanoic acid, 2,2-dimethyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar1442. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar1443. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1413. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar1414. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B

Iodide + Propanoic acid, 2,2-dimethyl- = (Iodide bullet Propanoic acid, 2,2-dimethyl-)

By formula: I- + C5H10O2 = (I- bullet C5H10O2)

Quantity Value Units Method Reference Comment
Deltar64.4 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar90.8J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar37. ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B

2,2-Dimethylpropanoic anhydride + Water = 2Propanoic acid, 2,2-dimethyl-

By formula: C10H18O3 + H2O = 2C5H10O2

Quantity Value Units Method Reference Comment
Deltar-63.26kJ/molCmConn, Kistiakowsky, et al., 1942liquid 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) = 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
350. MN/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
10.08EIHolmes, Fingas, et al., 1981LLK
10.3PEGreen and Hayes, 1975Vertical value; LLK

De-protonation reactions

C5H9O2- + Hydrogen cation = Propanoic acid, 2,2-dimethyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar1442. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar1443. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1413. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar1414. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas 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

Iodide + Propanoic acid, 2,2-dimethyl- = (Iodide bullet Propanoic acid, 2,2-dimethyl-)

By formula: I- + C5H10O2 = (I- bullet C5H10O2)

Quantity Value Units Method Reference Comment
Deltar64.4 ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar90.8J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar37. ± 4.2kJ/molTDAsCaldwell and Kebarle, 1984gas 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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IR spectrum
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Additional Data

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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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-1453
NIST MS number 229708

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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), NIST Free Links, 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

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillarySupelcowax-101527.Chung, Fung, et al., 200560. m/0.25 mm/0.25 «mu»m, 35. C @ 5. min, 6. K/min, 195. C @ 60. min

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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5864.Zhao, Li, et al., 200830. m/0.25 mm/0.25 «mu»m; 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

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Column type Active phase I Reference Comment
CapillaryRTX-Wax1563.Prososki, Etzel, et al., 200730. m/0.25 mm/0.5 «mu»m, He, 40. C @ 5. min, 10. K/min, 220. C @ 10. min
CapillaryTC-Wax1568.Suhardi, Suzuki, et al., 200260. m/0.25 mm/0.25 «mu»m, He, 40. C @ 10. min, 3. K/min, 230. C @ 10. min
CapillaryDB-Wax1579.Sekiwa, Kubota, et al., 1997He, 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

View large format table.

Column type Active phase I Reference Comment
CapillarySOLGel-Wax1586.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 «mu»m, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min)
CapillarySOLGel-Wax1579.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 «mu»m, 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, «alpha»-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