Propane, 2,2-dimethoxy-

Formula: C₅H₁₂O₂
Molecular weight: 104.1476
IUPAC Standard InChI: InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
IUPAC Standard InChIKey: HEWZVZIVELJPQZ-UHFFFAOYSA-N
CAS Registry Number: 77-76-9
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Acetone, dimethyl acetal; Acetone dimethyl ketal; 2,2-Dimethoxypropane
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-425. ± 1.	kJ/mol	Cm	Wiberg, Morgan, et al., 1994	ALS
Δ_fH°_gas	-424.31 ± 0.98	kJ/mol	Cm	Wiberg and Squires, 1979	Hydrolysis; ALS
Δ_fH°_gas	-421.9	kJ/mol	N/A	Stern and Dorer, 1962	Value computed using Δ_fH_liquid° value of -457.1±1.0 kj/mol from Stern and Dorer, 1962 and Δ_vapH° value of 35.2 kj/mol from Wiberg and Squires, 1979.; DRB

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-460.7 ± 0.8	kJ/mol	Cm	Wiberg, Morgan, et al., 1994	ALS
Δ_fH°_liquid	-459.48 ± 0.64	kJ/mol	Cm	Wiberg and Squires, 1979	Hydrolysis; ALS
Δ_fH°_liquid	-457.06 ± 0.96	kJ/mol	Cm	Stern and Dorer, 1962	Reanalyzed by Cox and Pilcher, 1970, Original value = -460. ± 2. kJ/mol; Heat of hydrolysis; ALS

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
217.7	298.15	Baglay, Gurariy, et al., 1988	T = 270 to 340 K. Unsmoothed experimental datum.; DH
218.0	298.15	Baglai, Baev, et al., 1984	T = 273 to 334 K. Cp(liq) = 2.75970 - 0.007898T + 1.9x10-5T2 kJ/kg*K (273 to 334 K).; DH

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	356.2	K	N/A	Weast and Grasselli, 1989	BS
T_boil	353.	K	N/A	American Tokyo Kasei, 1988	BS
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	37.6 ± 0.4	kJ/mol	GS	Verevkin, 2002	Based on data from 272. to 301. K.; AC
Δ_vapH°	35.7	kJ/mol	N/A	Wiberg, Morgan, et al., 1994	DRB
Δ_vapH°	35.27	kJ/mol	E	Wiberg and Squires, 1979	Hydrolysis; ALS
Δ_vapH°	35.2	kJ/mol	N/A	Wiberg and Squires, 1979	DRB
Δ_vapH°	29.4	kJ/mol	V	Stern and Dorer, 1962	Heat of hydrolysis; ALS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
38.2 ± 0.4	272. to 301.	GS	Verevkin, Peng, et al., 1998	AC
35.3	324.	EB	Wiberg, Morgan, et al., 1994	Based on data from 299. to 348. K.; AC
33.4 ± 0.2	325.	N/A	Baglay, Gurariy, et al., 1988	Based on data from 292. to 357. K.; AC

Gas phase ion energetics data

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Data compiled by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₄H₉O⁺	10.28 ± 0.05	CH₃O	EI	Martin, Lampe, et al., 1966

References

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Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., A microprocessor-controlled system for precise measurement of temperature changes. Determination of the enthalpies of hydrolysis of some polyoxygenated hydrocarbons, J. Chem. Thermodyn., 1979, 11, 773-786. [all data]

Stern and Dorer, 1962
Stern, J.H.; Dorer, F.H., Standard heats of formation of 2,2-Dimethoxypropane (1), and 2,2 -Diethoxypropane (1). Group additivity theory and calculated heats of formation and five ketals, J. Phys. Chem., 1962, 66, 97-99. [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]

Baglay, Gurariy, et al., 1988
Baglay, A.K.; Gurariy, L.L.; Kuleshov, G.G., Physical properties of compounds used in vitamin synthesis, J. Chem. Eng. Data, 1988, 33, 512-518. [all data]

Baglai, Baev, et al., 1984
Baglai, A.K.; Baev, A.A.; Belousov, V.P.; Beregovykh, V.V.; Grushenko, M.M.; Gurarii, L.L.; Konstantinov, S.G.; Kostyushko, Yu.L.; Kuleshov, G.G.; Pasechnik, N.I.; Petrashkevich, R.I.; Podkovyrov, A.I.; Sitnov, A.A.; Shishko, M.A.; Shulgin, I.L., Investigation of the physico-chemical characteristics of substances utilized in the synthesis of vitamins A and E, Khim. Farm. Zhur., 1984, 18, 1013-1019. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

American Tokyo Kasei, 1988
American Tokyo Kasei, TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]

Verevkin, 2002
Verevkin, Sergey P., Improved Benson Increments for the Estimation of Standard Enthalpies of Formation and Enthalpies of Vaporization of Alkyl Ethers, Acetals, Ketals, and Ortho Esters, J. Chem. Eng. Data, 2002, 47, 5, 1071-1097, https://doi.org/10.1021/je020023o . [all data]

Verevkin, Peng, et al., 1998
Verevkin, S.P.; Peng, W.-H.; Beckhaus, H.D.; Rücuardt, C., Geminal substituent effects. 16. Does the anomeric effect in ketals depend on the hybridization of the central carbon atom?, Eur. J. Org. Chem., 1998, 11, 2323. [all data]

Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W., An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes, J. Am. Chem. Soc., 1966, 88, 1353. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
T_boil	Boiling point
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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