2-Methyl-1-butene
- Formula: C5H10
- Molecular weight: 70.1329
- IUPAC Standard InChIKey: MHNNAWXXUZQSNM-UHFFFAOYSA-N
- CAS Registry Number: 563-46-2
- 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-Butene, 2-methyl-; γ-Isoamylene; 1-Isoamylene; C2H5C(CH3)=CH2; 2-Methylbutene-1; Isopentene; UN 2371; UN 2459; 2-methylbut-1-ene
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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 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 | -35.1 ± 0.84 | kJ/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
ΔfH°gas | -34.8 | kJ/mol | N/A | Good and Smith, 1979 | Value computed using ΔfHliquid° value of -60.96±0.84 kj/mol from Good and Smith, 1979 and ΔvapH° value of 26.19 kj/mol from missing citation.; DRB |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
102.97 | 273.15 | McCullough J.P., 1959 | Results of more recent statistical calculation [ Durig J.R., 1980] are different from recommended and experimental values up to 3 J/mol*K for S(T) and Cp(T).; GT |
109.96 | 298.15 | ||
110.50 | 300. | ||
138.91 | 400. | ||
164.85 | 500. | ||
187.11 | 600. | ||
206.10 | 700. | ||
222.38 | 800. | ||
236.48 | 900. | ||
248.66 | 1000. | ||
259.24 | 1100. | ||
268.40 | 1200. | ||
276.35 | 1300. | ||
283.30 | 1400. | ||
289.32 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
116.15 ± 0.35 | 320.66 | Scott D.W., 1949 | GT |
128.37 ± 0.39 | 362.51 | ||
140.62 ± 0.42 | 407.11 | ||
153.13 ± 0.46 | 453.41 | ||
165.35 ± 0.50 | 502.21 |
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 by: 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
By formula: H2 + C5H10 = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -126.95 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; At 355 °K |
ΔrH° | -118.2 ± 0.42 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -119.2 ± 1.5 kJ/mol; At 355 K |
By formula: C5H10 + CH4O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.8 | kJ/mol | Eqk | Serda, Izquierdo, et al., 1995 | liquid phase |
ΔrH° | -20.4 ± 0.8 | kJ/mol | Eqk | Hwang and Wu, 1994 | liquid phase |
ΔrH° | -33.6 ± 5.1 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Alcohol/alkane mixture |
By formula: C5H10 = C5H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -6.7 ± 3.0 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Methanol/H+ |
ΔrH° | -8.0 ± 1.4 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Ethanol/H+ |
By formula: C5H10 + HCl = C5H11Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -63.7 ± 1.4 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C5H10 + C2H6O = C7H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.2 ± 5.8 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Alcohol/alkane mixture |
By formula: C5H10 + C2HF3O2 = C7H11F3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -45.7 ± 0.2 | kJ/mol | Cm | Wiberg and Hao, 1991 | liquid phase; Trifuoroacetolysis |
By formula: C5H10 = C5H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.08 ± 0.50 | kJ/mol | Eqk | Radyuk, Kabo, et al., 1973 | gas phase; Heat of isomerization at 562 K |
By formula: C5H10 + CH4O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.8 ± 1.3 | kJ/mol | Eqk | Serda, Izquierdo, et al., 1995 | liquid phase |
By formula: C6H14O = C5H10 + CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 67.96 ± 0.39 | kJ/mol | Eqk | Rozhnov, Safronov, et al., 1991 | liquid phase |
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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C5H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.12 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.10 | PI | Traeger, 1986 | LBLHLM |
9.148 ± 0.003 | PE | Masclet, Grosjean, et al., 1973 | LLK |
9.12 | EI | Lossing, 1972 | LLK |
9.35 ± 0.08 | EI | Gross and Wilkins, 1971 | LLK |
9.12 ± 0.02 | PI | Demeo and El-Sayed, 1970 | RDSH |
9.12 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.2 ± 0.1 | PE | Bieri, Burger, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H6+ | 11.66 ± 0.06 | C2H4 | EI | Gross and Wilkins, 1971 | LLK |
C4H7+ | 10.66 | CH3 | PI | Traeger, 1986 | LBLHLM |
C4H7+ | 10.85 | CH3 | EI | Brand and Baer, 1984 | LBLHLM |
C4H7+ | 10.85 | CH3 | EI | Lossing, 1972 | LLK |
C4H7+ | 11.34 ± 0.07 | CH3 | EI | Gross and Wilkins, 1971 | LLK |
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
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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-1330 |
NIST MS number | 229038 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Reaction 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Download spectrum in JCAMP-DX format.
Source | Loeffler, Eberlin, et al., 1958 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 1285 |
Instrument | Fluorite prism vacuum spectrograph |
Melting point | -137.5 |
Boiling point | 31.2 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
Good and Smith, 1979
Good, W.D.; Smith, N.K.,
The enthalpies of combustion of the isomeric pentenes in the liquid state. A warning to combustion calorimetrists about sample drying,
J. Chem. Thermodyn., 1979, 11, 111-118. [all data]
McCullough J.P., 1959
McCullough J.P.,
Thermodynamic properties, vibrational assignment and rotational conformations of 2-methyl-1-butene,
J. Am. Chem. Soc., 1959, 81, 1331-1334. [all data]
Durig J.R., 1980
Durig J.R.,
Torsional spectra of molecules with two internal C3v rotors. 19. Vibrational spectra, torsional potential functions, and conformational and thermodynamic properties of 2-methyl-1-butene,
J. Phys. Chem., 1980, 84, 3554-3561. [all data]
Scott D.W., 1949
Scott D.W.,
Thermodynamic properties of three isomeric pentenes,
J. Am. Chem. Soc., 1949, 71, 2767-2773. [all data]
Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E.,
Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons,
J. Am. Chem. Soc., 1937, 59, 831-841. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. III. Hydrogenation of some higher olefins,
J. Am. Chem. Soc., 1936, 58, 137-145. [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]
Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M.,
Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition,
Thermochim. Acta, 1995, 259, 111-120. [all data]
Hwang and Wu, 1994
Hwang, W.-S.; Wu, J.-C.,
Kinetics and thermodynamics of synthesis of tertiary-amyl methyl ether catalyzed by ion-exchange resin,
J. Chin. Chem. Soc. (Taipei), 1994, 41, 181-186. [all data]
Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O.,
Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase,
J. Chem. Eng. Data, 1994, 39, 700-704. [all data]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]
Radyuk, Kabo, et al., 1973
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N.,
Isomerization equilibrium and thermodynamic properties of methylbutenes,
Neftekhimiya, 1973, 13, 356-360. [all data]
Rozhnov, Safronov, et al., 1991
Rozhnov, A.M.; Safronov, V.V.; Verevkin, S.P.; Sharonov, K.G.; Alenin, V.I.,
Enthalpy of combustion and enthalpy of vaporization of 2-ethyl-2-methoxypropane and thermodynamics of its gas-phase synthesis from (methanol + a 2-methylbutene),
J. Chem. Thermodyn., 1991, 23, 629-635. [all data]
Traeger, 1986
Traeger, J.C.,
Heat of formation for the 1-methylallyl cation by photoionization mass spectrometry,
J. Phys. Chem., 1986, 90, 4114. [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]
Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C3H3, C3H5, and C4H7 radicals and ions,
Can. J. Chem., 1972, 50, 3973. [all data]
Gross and Wilkins, 1971
Gross, M.L.; Wilkins, C.L.,
Computer-assisted ion cyclotron resonance appearance potential measurements for C5H10 isomers,
Anal. Chem., 1971, 43, 1624. [all data]
Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A.,
Ionization potential and structure of olefins,
J. Chem. Phys., 1970, 52, 2622. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]
Brand and Baer, 1984
Brand, W.A.; Baer, T.,
Dissociation dynamics of energy-selected C5H10+ ions,
J. Am. Chem. Soc., 1984, 106, 3154. [all data]
Loeffler, Eberlin, et al., 1958
Loeffler, B.B.; Eberlin, E.; Pickett, L.W.,
Far ultraviolet absorption spectra of small ring hydrocarbons,
J. Chem. Phys., 1958, 28, 2, 345-347. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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