1-Butyne, 3,3-dimethyl-
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChIKey: PPWNCLVNXGCGAF-UHFFFAOYSA-N
- CAS Registry Number: 917-92-0
- 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: t-Butylacetylene; tert-Butylacetylene; 3,3-Dimethyl-1-Butyne; 3,3-Dimethylbutyne; 3,3,3-Trimethylpropyne; (CH3)3CC≡CH; 3,3-Dimethylbutyne-1
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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 |
---|---|---|---|---|---|
ΔfH°gas | 106.1 | kJ/mol | Ccr | Pimenova, Kozina, et al., 1986 | ALS |
ΔfH°gas | 107.0 ± 1.3 | kJ/mol | Ion | Siretskaya, Takhistov, et al., 1986 | ALS |
ΔfH°gas | 106.7 | kJ/mol | N/A | Kupreev and Shimonaev, 1977 | Value computed using ΔfHliquid° value of 78.5±2.4 kj/mol from Kupreev and Shimonaev, 1977 and ΔvapH° 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 |
---|---|---|---|
36.75 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
56.59 | 100. | ||
77.26 | 150. | ||
96.13 | 200. | ||
122.51 | 273.15 | ||
131.31 | 298.15 | ||
131.95 | 300. | ||
164.76 | 400. | ||
192.40 | 500. | ||
215.05 | 600. | ||
233.85 | 700. | ||
249.77 | 800. | ||
263.45 | 900. | ||
275.27 | 1000. | ||
285.5 | 1100. | ||
294.4 | 1200. | ||
302.2 | 1300. | ||
308.9 | 1400. | ||
314.8 | 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 77.9 ± 1.5 | kJ/mol | Ccr | Pimenova, Kozina, et al., 1986 | |
ΔfH°liquid | 77.8 ± 1.3 | kJ/mol | Ion | Siretskaya, Takhistov, et al., 1986 | |
ΔfH°liquid | 78.5 ± 2.4 | kJ/mol | Ccb | Kupreev and Shimonaev, 1977 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3868.1 ± 1.3 | kJ/mol | Ccr | Pimenova, Kozina, et al., 1986 | Corresponding ΔfHºliquid = 77.9 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -3868.7 ± 2.4 | kJ/mol | Ccb | Kupreev and Shimonaev, 1977 | Corresponding ΔfHºliquid = 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 |
---|---|---|---|---|---|
Tboil | 311. ± 1. | K | AVG | N/A | Average of 16 out of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 194.94 | K | N/A | Pomerantz, Fookson, et al., 1954 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 192.0 | K | N/A | Van Risseghem, 1922 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 192. | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 28.2 | kJ/mol | E | Pimenova, Kozina, et al., 1986 | ALS |
ΔvapH° | 29.20 | kJ/mol | E | Siretskaya, Takhistov, et al., 1986 | ALS |
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- + =
By formula: C6H9- + H+ = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1582. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1549. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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 |
---|---|---|---|
9.86 | PI | Orlov, Boganov, et al., 1985 | LBLHLM |
9.80 ± 0.05 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
9.92 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.923 ± 0.010 | PE | Carlier, Dubois, et al., 1975 | LLK |
10.67 ± 0.02 | EI | MacLean and Sacher, 1974 | LLK |
10.31 ± 0.04 | EI | Bock and Seidl, 1968 | RDSH |
10.21 | PE | Cabelli, Cowley, et al., 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 14.7 | C5H7 | EI | SenSharma and Franklin, 1973 | LLK |
C5H7+ | 9.86 | CH3 | PI | Orlov, Boganov, et al., 1985 | LBLHLM |
C5H7+ | 9.90 ± 0.05 | CH3 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
C5H7+ | 9.86 ± 0.05 | CH3 | PI | Takhistov, Khlebnikova, et al., 1980 | LLK |
C5H7+ | 10.76 ± 0.06 | CH3 | EI | MacLean and Sacher, 1974 | LLK |
De-protonation reactions
C6H9- + =
By formula: C6H9- + H+ = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1582. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1549. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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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Additional Data
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Download spectrum in JCAMP-DX format.
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)
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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
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 114416 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 80. | 467. | Soják, Farkas, et al., 1991 | 107. m/0.25 mm/0.40 μm, H2 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 509. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 498. | Zenkevich and Marinichev, 2001 | Program: not specified |
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), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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 π-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]
Soják, Farkas, et al., 1991
Soják, L.; Farkas, P.; Ostrovský, I.; Janák, J.; Chrétien, J.R.,
Capillary gas chromatography of C5 - C13 branched alkynes on squalane and liquid crystal stationary phases,
J. Chromatogr., 1991, 557, 241-253, https://doi.org/10.1016/S0021-9673(01)87136-3
. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Zenkevich and Marinichev, 2001
Zenkevich, I.G.; Marinichev, A.N.,
Comparison of Topological and Dynamics Molecular Characteristics for Precalculation of Chromatographic Retention Parameters of Organic Compounds (in Russian),
Zh. Struct. Khim., 2001, 42, 5, 893-902. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tfus Fusion (melting) point 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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