1,2-Butadiene, 3-methyl-
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: PAKGDPSCXSUALC-UHFFFAOYSA-N
- CAS Registry Number: 598-25-4
- 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: 1,1-Dimethylallene; 1,1-Dimethylallylene; 2-Methyl-2,3-butadiene; 3-Methyl-1,2-butadiene; 3,3-Dimethylallene; CH2=C=C(CH3)2; 3-methylbuta-1,2-diene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 129.07 ± 0.57 | kJ/mol | Ccr | Steele, Chirico, et al., 1990 | ALS |
ΔfH°gas | 129.1 | kJ/mol | N/A | Good, 1969 | Value computed using ΔfHliquid° value of 101.2±0.5 kj/mol from Good, 1969 and ΔvapH° value of 27.9 kj/mol from missing citation.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 321.21 | J/mol*K | N/A | Messerly J.F., 1970 | GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.20 | 50. | Thermodynamics Research Center, 1997 | GT |
55.62 | 100. | ||
69.75 | 150. | ||
82.12 | 200. | ||
99.38 | 273.15 | ||
105.25 | 298.15 | ||
105.68 | 300. | ||
128.46 | 400. | ||
149.03 | 500. | ||
166.94 | 600. | ||
182.47 | 700. | ||
196.0 | 800. | ||
207.7 | 900. | ||
217.9 | 1000. | ||
226.8 | 1100. | ||
234.5 | 1200. | ||
241.1 | 1300. | ||
246.8 | 1400. | ||
251.8 | 1500. |
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°liquid | 101.2 ± 0.50 | kJ/mol | Ccb | Good, 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3212.1 ± 0.42 | kJ/mol | Ccb | Good, 1969 | Corresponding ΔfHºliquid = 101.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 231.79 | J/mol*K | N/A | Messerly, Todd, et al., 1970 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
152.42 | 298.15 | Messerly, Todd, et al., 1970 | T = 12 to 320 K.; DH |
151.1 | 298.15 | Good, 1969 | 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 312. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 159.510 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 159.510 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 159.520 | K | N/A | Streiff, Schultz, et al., 1957 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 159.53 | K | N/A | Messerly, Todd, et al., 1970, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 27.90 ± 0.28 | kJ/mol | V | Steele, Chirico, et al., 1990 | ALS |
ΔvapH° | 28. | kJ/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
31. | 240. | A | Stephenson and Malanowski, 1987 | Based on data from 227. to 253. K.; AC |
29.9 | 267. | A | Stephenson and Malanowski, 1987 | Based on data from 252. to 323. K.; AC |
31.6 | 230. | IP | Osborn and Douslin, 1969 | Based on data from 213. to 242. K.; AC |
29. | 291. | EB | Osborn and Douslin, 1969 | Based on data from 274. to 319. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
213.14 to 242.22 | 4.41572 | 1249.41 | -29.226 | Osborn and Douslin, 1969 | Coefficents calculated by NIST from author's data. |
273.73 to 319.19 | 4.07332 | 1106.62 | -41.93 | Osborn and Douslin, 1969 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.9563 | 159.53 | Messerly, Todd, et al., 1970 | DH |
7.95 | 159.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
49.873 | 159.53 | Messerly, Todd, et al., 1970 | DH |
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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C5H8+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.9 | EI | Harris, McKinnon, et al., 1979 | |
8.95 ± 0.02 | PE | Bieri, Burger, et al., 1977 | |
8.95 | PE | Brogli, Crandall, et al., 1973 | Vertical value |
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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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 | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
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-IW-3675 |
NIST MS number | 231201 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of ideal-gas enthalpies of formation for key compounds,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]
Good, 1969
Good, W.D.,
3-Methyl-1,2-butadiene: Enthalpies of combustion and formation,
J. Chem. Eng. Data, 1969, 14, 480-481. [all data]
Messerly J.F., 1970
Messerly J.F.,
Chemical thermodynamic properties of the pentadienes. Third law studies,
J. Chem. Eng. Data, 1970, 15, 227-232. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Messerly, Todd, et al., 1970
Messerly, J.F.; Todd, S.S.; Guthrie, G.B.,
Chemical thermodynamic properties of the pentadienes,
J. Chem. Eng. Data, 1970, 15, 227-232. [all data]
Streiff, Schultz, et al., 1957
Streiff, A.J.; Schultz, L.H.; Hulme, A.R.; Tucker, J.A.; Krouskop, N.C.; Rossini, F.D.,
Purification, Purity, and Freezing Points of 20 API Standard API Research Hydrocarbons,
Anal. Chem., 1957, 29, 361. [all data]
Messerly, Todd, et al., 1970, 2
Messerly, J.F.; Todd, S.S.; Guthrie, G.B.,
Chemical thermodynamic properties of the pentadienes. Third law studies.,
J. Chem. Eng. Data, 1970, 15, 227-32. [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]
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]
Osborn and Douslin, 1969
Osborn, Ann G.; Douslin, Donald R.,
Vapor pressure relations for the seven pentadienes,
J. Chem. Eng. Data, 1969, 14, 2, 208-209, https://doi.org/10.1021/je60041a010
. [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]
Harris, McKinnon, et al., 1979
Harris, D.; McKinnon, S.; Boyd, R.K.,
The origins of the base peak in the electron impact spectrum of limonene,
Org. Mass Spectrom., 1979, 14, 265. [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]
Brogli, Crandall, et al., 1973
Brogli, F.; Crandall, J.K.; Heilbronner, E.; Kloster-Jensen, E.; Sojka, S.A.,
The photoelectron spectra of methyl-substituted allenes and of tetramethyl-bisallenyl,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 455. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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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