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
Go To: Top, Phase change data, Gas phase ion energetics data, 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 | 25.36 | kcal/mol | Ccr | Pimenova, Kozina, et al., 1986 | ALS |
ΔfH°gas | 25.57 ± 0.31 | kcal/mol | Ion | Siretskaya, Takhistov, et al., 1986 | ALS |
ΔfH°gas | 25.50 | kcal/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 (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.783 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
13.53 | 100. | ||
18.47 | 150. | ||
22.98 | 200. | ||
29.281 | 273.15 | ||
31.384 | 298.15 | ||
31.537 | 300. | ||
39.379 | 400. | ||
45.985 | 500. | ||
51.398 | 600. | ||
55.891 | 700. | ||
59.696 | 800. | ||
62.966 | 900. | ||
65.791 | 1000. | ||
68.24 | 1100. | ||
70.36 | 1200. | ||
72.23 | 1300. | ||
73.83 | 1400. | ||
75.24 | 1500. |
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° | 6.74 | kcal/mol | E | Pimenova, Kozina, et al., 1986 | ALS |
ΔvapH° | 6.979 | kcal/mol | E | Siretskaya, Takhistov, et al., 1986 | ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, 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:
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° | 378.0 ± 2.2 | kcal/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° | 370.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas 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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