2-Butene, 2,3-dimethyl-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: WGLLSSPDPJPLOR-UHFFFAOYSA-N
- CAS Registry Number: 563-79-1
- 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: Tetramethylethylene; 1,1,2,2-Tetramethylethylene; 2,3-Dimethyl-2-butene; 2,3-Dimethylbut-2-ene; 2,3-Dimethylbutene-2; (CH3)2C=C(CH3)2; Tetramethylethene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -16.80 ± 0.36 | kcal/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
ΔfH°gas | -16.35 ± 0.35 | kcal/mol | Eqk | Rodgers and Wu, 1971 | Heat of isomerization; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.340 ± 0.065 | 334.20 | Scott D.W., 1955 | GT |
33.939 ± 0.067 | 355.25 | ||
36.960 ± 0.074 | 393.20 | ||
40.069 ± 0.081 | 433.20 | ||
43.100 ± 0.086 | 473.20 |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
27.710 | 273.15 | Scott D.W., 1955 | Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT |
29.541 | 298.15 | ||
29.680 | 300. | ||
37.481 | 400. | ||
45.041 | 500. | ||
51.781 | 600. | ||
57.670 | 700. | ||
62.780 | 800. | ||
67.249 | 900. | ||
71.140 | 1000. | ||
74.551 | 1100. | ||
77.510 | 1200. | ||
80.079 | 1300. | ||
82.330 | 1400. | ||
84.309 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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 | -24.60 ± 0.35 | kcal/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 64.579 | cal/mol*K | N/A | Scott, Finke, et al., 1955 | DH |
S°liquid | 65.11 | cal/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 58.45 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.750 | 298.15 | Scott, Finke, et al., 1955 | T = 10 to 320 K.; DH |
42.000 | 295.5 | Parks, Todd, et al., 1936 | T = 83 to 296 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 346.3 ± 0.4 | K | AVG | N/A | Average of 28 out of 30 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 198.8 ± 0.3 | K | AVG | N/A | Average of 13 out of 15 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 198.92 | K | N/A | Scott, Finke, et al., 1955, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 198.900 | K | N/A | Waddington, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 198.920 | K | N/A | Waddington, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 198.5 | K | N/A | Parks, Todd, et al., 1936, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 524. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.808 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.77 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 7.78 | kcal/mol | V | Camin and Rossini, 1956 | ALS |
ΔvapH° | 7.79 | kcal/mol | N/A | Camin and Rossini, 1956, 2 | Based on data from 289. to 347. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.084 | 346.4 | N/A | Majer and Svoboda, 1985 | |
7.67 | 328. | N/A | Uusi-Kyyny, Pokki, et al., 2004 | Based on data from 313. to 346. K.; AC |
7.91 | 297. | A | Stephenson and Malanowski, 1987 | Based on data from 282. to 348. K. See also Bevan, Malkin, et al., 1955.; AC |
7.82 | 304. | N/A | Fried, Baghdoyan, et al., 1971 | Based on data from 289. to 347. K.; AC |
7.86 ± 0.02 | 292. | C | Scott, Finke, et al., 1955 | AC |
7.65 ± 0.02 | 308. | C | Scott, Finke, et al., 1955 | AC |
7.39 ± 0.02 | 326. | C | Scott, Finke, et al., 1955 | AC |
7.10 ± 0.02 | 346. | C | Scott, Finke, et al., 1955 | 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 |
---|---|---|---|---|---|
292. to 346. | 11.54 | 0.2801 | 524. | 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 |
---|---|---|---|---|---|
289.48 to 347.00 | 3.69897 | 1021.564 | -70.242 | Baghdoyan, Malik, et al., 1971 | Coefficents calculated by NIST from author's data. |
302.18 to 346.36 | 4.09016 | 1224.926 | -46.812 | Scott, Finke, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.54 | 198.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.288 | 196.8 | Domalski and Hearing, 1996 | CAL |
7.741 | 198.9 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.8439 | 196.82 | crystaline, II | crystaline, I | Scott, Finke, et al., 1955 | DH |
1.542 | 198.92 | crystaline, I | liquid | Scott, Finke, et al., 1955 | Enthalpies of transition and fusion calculated from total enthalpy change 196.82 to 198.92 K and assumed Cp of 150 J/mol*K for c,I.; DH |
1.094 | 196.6 | crystaline, II | crystaline, I | Parks, Todd, et al., 1936 | DH |
1.305 | 198.5 | crystaline, I | liquid | Parks, Todd, et al., 1936 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
4.288 | 196.82 | crystaline, II | crystaline, I | Scott, Finke, et al., 1955 | DH |
7.753 | 198.92 | crystaline, I | liquid | Scott, Finke, et al., 1955 | Enthalpies; DH |
5.564 | 196.6 | crystaline, II | crystaline, I | Parks, Todd, et al., 1936 | DH |
6.575 | 198.5 | crystaline, I | liquid | Parks, Todd, et al., 1936 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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:
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 C6H12+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.27 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 194.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 187.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.27 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
8.16 | EI | Lossing and Traeger, 1975 | LLK |
8.271 ± 0.005 | PE | Masclet, Grosjean, et al., 1973 | LLK |
8.26 | PE | Frost and Sandhu, 1971 | LLK |
8.30 | PI | Bralsford, Harris, et al., 1960 | RDSH |
8.30 | PE | Kovac, Mohraz, et al., 1980 | Vertical value; LLK |
10.52 | PE | McAlduff and Houk, 1977 | Vertical value; LLK |
8.46 | PE | Mollere, Houk, et al., 1976 | Vertical value; LLK |
8.42 | PE | Fuss and Bock, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H9+ | 8.16 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H9+ | 10.32 | CH3 | EI | Lossing and Traeger, 1975 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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-3539 |
NIST MS number | 230825 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S.,
Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols,
J. Org. Chem., 1991, 56, 5108-5110. [all data]
Rodgers and Wu, 1971
Rodgers, A.S.; Wu, M.-C.R.,
Thermochemistry of the gas-phase iodine catalyzed isomerization: 2,3-dimethyl-1-butene = 2,3-dimethyl-2-butene,
J. Chem. Thermodyn., 1971, 3, 591-597. [all data]
Scott D.W., 1955
Scott D.W.,
2,3-Dimethyl-2-butene: thermodynamic properties in the solid, liquid and vapor states,
J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]
Scott, Finke, et al., 1955
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2,3-Dimethyl-2-butene: Thermodynamic properties in the solid, liquid and vapor states,
J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505-2508. [all data]
Scott, Finke, et al., 1955, 2
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
2,3-dimethyl-2-butene: thermodynamic properties in the solid, liquid, and vapor states.,
J. Am. Chem. Soc., 1955, 77, 4993. [all data]
Waddington, 1951
Waddington, G.,
Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1951. [all data]
Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H.,
Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins,
J. Am. Chem. Soc., 1936, 58, 2505. [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]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Camin and Rossini, 1956
Camin, D.L.; Rossini, F.D.,
Physical properties of the 17 isomeric hexenes of the API research series,
J. Phys. Chem., 1956, 60, 1446. [all data]
Camin and Rossini, 1956, 2
Camin, David L.; Rossini, Frederick D.,
Physical Properties of the 17 Isomeric Hexenes.of the API Research Series,
J. Phys. Chem., 1956, 60, 10, 1446-1451, https://doi.org/10.1021/j150544a029
. [all data]
Uusi-Kyyny, Pokki, et al., 2004
Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Kim, Younghun; Aittamaa, Juhani,
Isobaric Vapor Liquid Equilibrium for 2,3-Dimethyl-2-butene + Methanol, + Ethanol, + 2-Propanol, or + 2-Butanol at Atmospheric Pressure,
J. Chem. Eng. Data, 2004, 49, 2, 251-255, https://doi.org/10.1021/je034106w
. [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]
Bevan, Malkin, et al., 1955
Bevan, T.H.; Malkin, T.; Smith, D.B.; Davey, W.; Gwilt, J.R.; Cooper, W.; Kertes, S.; Roberts, J.J.; Ross, W.C.J.; Wilson, Walter; Cummings, G.A.McD.; McLaughlin, E.,
Notes,
J. Chem. Soc., 1955, 1383, https://doi.org/10.1039/jr9550001383
. [all data]
Fried, Baghdoyan, et al., 1971
Fried, Vojtech.; Baghdoyan, Armen.; Malik, Jana.,
Vapor pressures and densities of 2,3-dimethyl-2-butene and 3,3-dimethyl-1-butene,
J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009
. [all data]
Baghdoyan, Malik, et al., 1971
Baghdoyan, A.; Malik, J.; Fried, V.,
Vapor Pressures and Densities of 2,3-Dimethyl-2-butene and 3,3-Dimethyl-1-butene,
J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P.,
Valence ionization enrgies of hydrocarbons,
Helv. Chim. Acta, 1977, 60, 2213. [all data]
Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C.,
Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations,
J. Am. Chem. Soc., 1975, 97, 1579. [all data]
Masclet, Grosjean, et al., 1973
Masclet, P.; Grosjean, D.; Mouvier, G.,
Alkene ionization potentials. Part I. Quantitative determination of alkyl group structural effects,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 225. [all data]
Frost and Sandhu, 1971
Frost, D.C.; Sandhu, J.S.,
Ionization potentials of ethylene and some methyl-substituted ethylenes as determined by photoelectron spectroscopy,
Indian J. Chem., 1971, 9, 1105. [all data]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Kovac, Mohraz, et al., 1980
Kovac, B.; Mohraz, M.; Heilbronner, E.; Boekelheide, V.; Hopf, H.,
Photoelectron spectra of the cyclophanes,
J. Am. Chem. Soc., 1980, 102, 4314. [all data]
McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N.,
Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals,
Can. J. Chem., 1977, 55, 318. [all data]
Mollere, Houk, et al., 1976
Mollere, P.D.; Houk, K.N.; Bomse, D.S.; Morton, T.H.,
Photoelectron spectra of sterically congested alkenes and dienes,
J. Am. Chem. Soc., 1976, 98, 4732. [all data]
Fuss and Bock, 1974
Fuss, W.; Bock, H.,
Photoelectron spectra and molecular properties. XXXVI. (H3C)3B, (H3C)2BF, (H3C)2BN(CH3)2, and (H3C)2CC(CH3)2: The use of ionization potentials in assigning UV spectra,
J. Chem. Phys., 1974, 61, 1613. [all data]
Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C.,
Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations.,
J. Am. Chem. Soc., 1975, 19, 9. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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