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1-Butene, 3,3-dimethyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
gas82.161cal/mol*KN/AStull D.R., 1969This value is based on the low-temperature results [ Kennedy W.D., 1938] for S(liquid).

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 by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
liquid37.40cal/mol*KN/AKennedy, Shomate, et al., 1938Extrapolation below 80 K, 47.66 J/mol*K.

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
45.000295.9Kennedy, Shomate, et al., 1938T = 80 to 298 K. Value is unsmoothed experimental datum.

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
Tboil314.4 ± 0.3KAVGN/AAverage of 22 out of 23 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus157.880KN/AStreiff, 1964Uncertainty assigned by TRC = 0.07 K; TRC
Tfus157.92KN/AStreiff, 1964Uncertainty assigned by TRC = 0.05 K; TRC
Tfus158.08KN/ABoord, Henne, et al., 1949Uncertainty assigned by TRC = 0.5 K; TRC
Tfus157.91KN/ABoord, Greenlee, et al., 1946Uncertainty assigned by TRC = 0.4 K; TRC
Tfus157.62KN/ABrooks, Howard, et al., 1940Uncertainty assigned by TRC = 0.06 K; TRC
Quantity Value Units Method Reference Comment
Ttriple158.4KN/AKennedy, Shomate, et al., 1938, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap6.36kcal/molN/AReid, 1972AC
Deltavap6.55kcal/molN/AFried, Baghdoyan, et al., 1971Based on data from 264. - 314. K.; AC
Deltavap6.36kcal/molVCamin and Rossini, 1956ALS
Deltavap6.36kcal/molN/ACamin and Rossini, 1956, 2Based on data from 281. - 315. K.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
6.84269.AStephenson and Malanowski, 1987Based on data from 254. - 316. K.; AC

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
263.69 - 314.663.896951062.207-41.84Baghdoyan, Malik, et al., 1971Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
0.261158.4Domalski and Hearing, 1996AC

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.039124.9crystaline, IIcrystaline, IKennedy, Shomate, et al., 1938DH
0.2620158.4crystaline, IIliquidKennedy, Shomate, et al., 1938DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
8.317124.9crystaline, IIcrystaline, IKennedy, Shomate, et al., 1938DH
1.65158.4crystaline, IIliquidKennedy, Shomate, et al., 1938DH

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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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

Hydrogen + 1-Butene, 3,3-dimethyl- = Butane, 2,2-dimethyl-

By formula: H2 + C6H12 = C6H14

Quantity Value Units Method Reference Comment
Deltar-30.07 ± 0.13kcal/molChydRogers, Crooks, et al., 1987liquid phase; ALS
Deltar-30.10 ± 0.15kcal/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -30.34 ± 0.15 kcal/mol; AT 355 °K; ALS

C6H11- + Hydrogen cation = 1-Butene, 3,3-dimethyl-

By formula: C6H11- + H+ = C6H12

Quantity Value Units Method Reference Comment
Deltar409.0 ± 4.0kcal/molCIDTGraul and Squires, 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar399.9 ± 4.1kcal/molH-TSGraul and Squires, 1990gas phase; B

1-Hexene = 1-Butene, 3,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Deltar-3.80 ± 0.30kcal/molCisoBartolo and Rossini, 1960liquid phase; Calculated from «DELTA»Hc; ALS

Butane, 2,2-dimethyl- = Hydrogen + 1-Butene, 3,3-dimethyl-

By formula: C6H14 = H2 + C6H12

Quantity Value Units Method Reference Comment
Deltar30.1 ± 0.2kcal/molCmKennedy, Shomate, et al., 1938liquid phase; ALS

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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H12+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.45 ± 0.02PEBieri, Burger, et al., 1977LLK
9.44EILossing and Traeger, 1975LLK
9.450 ± 0.005PEMasclet, Grosjean, et al., 1973LLK
9.62 ± 0.04EIBock and Seidl, 1968RDSH
9.7PEWeidner and Schweig, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+15.4C5H9EISenSharma and Franklin, 1973LLK
C5H9+9.44CH3EILossing and Traeger, 1975, 2LLK
C5H9+10.14CH3EILossing and Traeger, 1975LLK

De-protonation reactions

C6H11- + Hydrogen cation = 1-Butene, 3,3-dimethyl-

By formula: C6H11- + H+ = C6H12

Quantity Value Units Method Reference Comment
Deltar409.0 ± 4.0kcal/molCIDTGraul and Squires, 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar399.9 ± 4.1kcal/molH-TSGraul and Squires, 1990gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 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-3189
NIST MS number 227595

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.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Jones and Taylor, 1955
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. 885
Instrument Beckman DU
Melting point -115.2
Boiling point 41.2

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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.

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Kennedy W.D., 1938
Kennedy W.D., Thermal data on organic compounds. XVIII. The heat capacity and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-1509. [all data]

Kennedy, Shomate, et al., 1938
Kennedy, Wm.D.; Shomate, C.H.; Parks, G.P., Thermal data on organic compounds. XVIII. The heat capacity of and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-1509. [all data]

Streiff, 1964
Streiff, A.J., , Am. Pet. Inst. Res. Proj. 58B Unpublished, 1964. [all data]

Boord, Henne, et al., 1949
Boord, C.E.; Henne, A.L.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M., The Grignard Reagent in hydrocarbon synthesis, Ind. Eng. Chem., 1949, 41, 609. [all data]

Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L., The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [all data]

Brooks, Howard, et al., 1940
Brooks, D.B.; Howard, F.L.; Crafton, H.C., Physical Properties of Some Purified Aliphatic Hydrocarbons, J. Res. Natl. Bur. Stand. (U. S.), 1940, 24, 33. [all data]

Kennedy, Shomate, et al., 1938, 2
Kennedy, W.D.; Shomate, C.H.; Parks, G.S., Thermal data on organic compounds: xviii the heat capacity and entropy of t-butylethylene, J. Am. Chem. Soc., 1938, 60, 1507-9. [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]

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]

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]

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]

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]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Bartolo and Rossini, 1960
Bartolo, H.F.; Rossini, F.D., Heats of isomerization of the seventeen isomeric hexenes, J. Phys. Chem., 1960, 64, 1685-1689. [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]

Bock and Seidl, 1968
Bock, H.; Seidl, H., d-Orbitaleffekte in siliziumsubstituierten «pi»-Elektronensystemen. VI. Spektroskopische Untersuchungen an Alkyl- und Silylathylenen, J. Organometal. Chem., 1968, 13, 87. [all data]

Weidner and Schweig, 1972
Weidner, U.; Schweig, A., Theory and application of photoelectron spectroscopy. V. The nature of bonding in vinyl- and allylsilanes: the effects of «sigma»-«pi» (hyperconjugation) p«pi»-d«pi» conjugation in these compounds, J. Organomet. Chem., 1972, 39, 261. [all data]

SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L., Heat of formation of free radicals by mass spectrometry, J. Am. Chem. Soc., 1973, 95, 6562. [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]

Jones and Taylor, 1955
Jones, L.C., Jr.; Taylor, L.W., Far ultraviolet absorption spectra of unsaturated and aromatic hydrocarbons, Anal. Chem., 1955, 27, 2, 228-237. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References