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1-Butyne, 3,3-dimethyl-

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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas106.1kJ/molCcrPimenova, Kozina, et al., 1986ALS
Deltafgas107.0 ± 1.3kJ/molIonSiretskaya, Takhistov, et al., 1986ALS
Deltafgas106.7kJ/molN/AKupreev and Shimonaev, 1977Value computed using «DELTA»fHliquid° value of 78.5±2.4 kj/mol from Kupreev and Shimonaev, 1977 and «DELTA»vapH° value of 28.2 kj/mol from Pimenova, Kozina, et al., 1986.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
36.7550.Thermodynamics Research Center, 1997p=1 bar.; GT
56.59100.
77.26150.
96.13200.
122.51273.15
131.31298.15
131.95300.
164.76400.
192.40500.
215.05600.
233.85700.
249.77800.
263.45900.
275.271000.
285.51100.
294.41200.
302.21300.
308.91400.
314.81500.

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid77.9 ± 1.5kJ/molCcrPimenova, Kozina, et al., 1986 
Deltafliquid77.8 ± 1.3kJ/molIonSiretskaya, Takhistov, et al., 1986 
Deltafliquid78.5 ± 2.4kJ/molCcbKupreev and Shimonaev, 1977 
Quantity Value Units Method Reference Comment
Deltacliquid-3868.1 ± 1.3kJ/molCcrPimenova, Kozina, et al., 1986Corresponding «DELTA»fliquid = 77.9 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-3868.7 ± 2.4kJ/molCcbKupreev and Shimonaev, 1977Corresponding «DELTA»fliquid = 78.45 kJ/mol (simple calculation by NIST; no Washburn corrections)

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil311. ± 1.KAVGN/AAverage of 16 out of 18 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus194.94KN/APomerantz, Fookson, et al., 1954Uncertainty assigned by TRC = 0.3 K; TRC
Tfus192.0KN/AVan Risseghem, 1922Uncertainty assigned by TRC = 1.5 K; TRC
Tfus192.KN/ATimmermans, 1922Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap28.2kJ/molEPimenova, Kozina, et al., 1986ALS
Deltavap29.20kJ/molESiretskaya, Takhistov, et al., 1986ALS

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 by: 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

C6H9- + Hydrogen cation = 1-Butyne, 3,3-dimethyl-

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar1582. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1549. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

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
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 C6H10+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.86PIOrlov, Boganov, et al., 1985LBLHLM
9.80 ± 0.05EIWolkoff, Holmes, et al., 1980LLK
9.92 ± 0.02PEBieri, Burger, et al., 1977LLK
9.923 ± 0.010PECarlier, Dubois, et al., 1975LLK
10.67 ± 0.02EIMacLean and Sacher, 1974LLK
10.31 ± 0.04EIBock and Seidl, 1968RDSH
10.21PECabelli, Cowley, et al., 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+14.7C5H7EISenSharma and Franklin, 1973LLK
C5H7+9.86CH3PIOrlov, Boganov, et al., 1985LBLHLM
C5H7+9.90 ± 0.05CH3EIWolkoff, Holmes, et al., 1980LLK
C5H7+9.86 ± 0.05CH3PITakhistov, Khlebnikova, et al., 1980LLK
C5H7+10.76 ± 0.06CH3EIMacLean and Sacher, 1974LLK

De-protonation reactions

C6H9- + Hydrogen cation = 1-Butyne, 3,3-dimethyl-

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar1582. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1549. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

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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IR 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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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, 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

View image of digitized spectrum (can be printed in landscape orientation).

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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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114416

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.


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), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Pimenova, Kozina, et al., 1986
Pimenova, S.M.; Kozina, M.P.; Gal'chenko, G.L.; Siretskaya, T.V.; Takhistov, V.V.; Kuznetsova, T.S.; Proskurnina, M.V.; Kotel'nikova, T.A., Heats of combustion and formation of some compounds with acetylene bonding, Termodin. Org. Soedin., 1986, 12-16. [all data]

Siretskaya, Takhistov, et al., 1986
Siretskaya, T.V.; Takhistov, V.V.; Pimenova, S.M.; Orlov, V.M.; Pustobaev, V.N., Formation enthalpies of acetylene ketones fragments in gas phases, React. Kinet. Catal. Lett., 1986, 31, 15-19. [all data]

Kupreev and Shimonaev, 1977
Kupreev, A.I.; Shimonaev, G.S., Determination of the enthalpies of formation of liquid acetylenic hydrocarbons, Russ. J. Phys. Chem. (Engl. Transl.), 1977, 51, 826-827. [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]

Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L., Synthesis and Physical Properties of Several Acetylenic Hydrocarbons, J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 51. [all data]

Van Risseghem, 1922
Van Risseghem, H., Synthesis of trimethylethylmethane, Bull. Soc. Chim. Belg., 1922, 31, 62-6. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Orlov, Boganov, et al., 1985
Orlov, V.M.; Boganov, A.M.; Siretskaya, T.V.; Takhistov, V.V., Thermochemical characteristics of the molecular and fragmentation ions of substituted tert-butylacetylenes, Izv. Akad. Nauk SSSR Ser. Khim., 1985, 12, 2795. [all data]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C6H10+ molecular ion structures, Can. J. Chem., 1980, 58, 251. [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]

Carlier, Dubois, et al., 1975
Carlier, P.; Dubois, J.E.; Masclet, P.; Mouvier, G., Spectres de photoelectrons des alcynes, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 55. [all data]

MacLean and Sacher, 1974
MacLean, D.I.; Sacher, R.E., A study of some spectroscopic properties of Group IVA acetylides, J. Organomet. Chem., 1974, 74, 197. [all data]

Bock and Seidl, 1968
Bock, H.; Seidl, H., d-Orbital effects in siliconsubstituted «pi»-electron systems. Part XII. Some spectroscopic properties of alkyl and silyl acetylenes and polyacetylenes, J. Chem. Soc. B, 1968, 1158. [all data]

Cabelli, Cowley, et al., 1981
Cabelli, D.E.; Cowley, A.H.; Dewar, M.J.S., UPE studies of conjugation involving group 5A elements. 2. Substituted tert-butylacetylenes, J. Am. Chem. Soc., 1981, 103, 3290. [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]

Takhistov, Khlebnikova, et al., 1980
Takhistov, V.; Khlebnikova, N.; Orlov, V., Photoionization study of energetic properties of cations formed with fragmentation of substituted acetylenes containing elements of IV B group, Org. React. Tartu, 1980, 17, 449. [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), References