1-Propene, 2-methyl-
- Formula: C4H8
- Molecular weight: 56.1063
- IUPAC Standard InChIKey: VQTUBCCKSQIDNK-UHFFFAOYSA-N
- CAS Registry Number: 115-11-7
- 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: Propene, 2-methyl-; γ-Butylene; Isobutene; Isobutylene; Isopropylidenemethylene; 1,1-Dimethylethylene; 2-Methyl-1-propene; 2-Methylpropene; iso-C4H8; Methylpropene; UN 1055; 1,1-Dimethylethene; 2-Methylpropylene
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -4.29 ± 0.26 | kcal/mol | Cm | Prosen, Maron, et al., 1951 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -645.19 ± 0.25 | kcal/mol | Cm | Prosen, Maron, et al., 1951 | Corresponding ΔfHºgas = -4.27 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°gas | -650.6 | kcal/mol | Ccb | Guinchant, 1918 | Corresponding ΔfHºgas = 1.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 70.170 | cal/mol*K | N/A | Stull D.R., 1969 | This value was obtained on the basis of calorimetric data [ Todd S.S., 1936]. Experimental value of S(298 K)=288.7 J/mol*K [ Todd S.S., 1936] could not be recommended because of its large uncertainty.; GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.528 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Recommended values are in close agreement with other statistically calculated values [ Kilpatrick J.E., 1946] as well as with ab initio value of S(298.15 K)=293.37 J/mol*K [ East A.L.L., 1997].; GT |
10.98 | 100. | ||
13.58 | 150. | ||
16.09 | 200. | ||
19.77 | 273.15 | ||
21.05 | 298.15 | ||
21.15 | 300. | ||
26.240 | 400. | ||
30.915 | 500. | ||
35.010 | 600. | ||
38.564 | 700. | ||
41.659 | 800. | ||
44.357 | 900. | ||
46.714 | 1000. | ||
48.764 | 1100. | ||
50.550 | 1200. | ||
52.101 | 1300. | ||
53.454 | 1400. | ||
54.632 | 1500. | ||
56.977 | 1750. | ||
58.678 | 2000. | ||
59.940 | 2250. | ||
60.894 | 2500. | ||
61.623 | 2750. | ||
62.189 | 3000. |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
18.13 ± 0.091 | 239.15 | Scott R.B., 1945 | GT |
19.81 ± 0.098 | 272.15 | ||
21.91 ± 0.11 | 312.15 | ||
23.96 ± 0.12 | 353.15 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
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
C4H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 393.0 ± 1.8 | kcal/mol | Endo | Wenthold, Hu, et al., 1999 | gas phase; B |
ΔrH° | 387.0 ± 2.0 | kcal/mol | D-EA | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrH° | 390.3 ± 2.3 | kcal/mol | G+TS | Bartmess and Burnham, 1984 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 385.6 ± 1.9 | kcal/mol | H-TS | Wenthold, Hu, et al., 1999 | gas phase; B |
ΔrG° | 379.6 ± 2.1 | kcal/mol | H-TS | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrG° | 382.9 ± 2.2 | kcal/mol | IMRE | Bartmess and Burnham, 1984 | gas phase; B |
By formula: H4N+ + C4H8 = (H4N+ • C4H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 35.0 | kcal/mol | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; condensation; M |
ΔrH° | 34.9 | kcal/mol | PHPMS | Meot-Ner (Mautner) and Sieck, 1990 | gas phase; forms t-C4H9NH3+; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 37.1 | cal/mol*K | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; condensation; M |
ΔrS° | 39.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner) and Sieck, 1990 | gas phase; forms t-C4H9NH3+; M |
By formula: C4H9Cl = C4H8 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.7 ± 0.5 | kcal/mol | Eqk | Howlett, 1955 | gas phase; ALS |
ΔrH° | 17.70 | kcal/mol | Eqk | Howlett, 1951 | gas phase; Hf-gas-(390) -44.4 kcal/mol; ALS |
ΔrH° | 17.1 ± 0.5 | kcal/mol | Eqk | Kistiakowsky and Stauffer, 1937 | gas phase; ALS |
By formula: C4H8 + C2H6O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.65 | kcal/mol | Cm | Sola, Pericas, et al., 1995 | liquid phase; ALS |
ΔrH° | -7.65 | kcal/mol | Kin | Sola, Pericas, et al., 1995 | liquid phase; ALS |
ΔrH° | -14.9 ± 0.5 | kcal/mol | Eqk | Iborra, Izquierdo, et al., 1989 | gas phase; GC; ALS |
By formula: C3H9Si+ + C4H8 = (C3H9Si+ • C4H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 36.5 | kcal/mol | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 42.7 | cal/mol*K | PHPMS | Li and Stone, 1989 | gas phase; condensation; M |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.15 ± 0.10 | kcal/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1935 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -28.39 ± 0.18 kcal/mol; At 355 °K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -19.4 ± 0.5 | kcal/mol | Eqk | Benson and Amano, 1962 | gas phase; ALS |
ΔrH° | -19.2 ± 1.0 | kcal/mol | Eqk | Jones and Ogg, 1937 | gas phase; At 408-464 K; ALS |
By formula: C4H8 + C3H8O = C7H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.47 ± 0.31 | kcal/mol | Eqk | Calderon, Tejero, et al., 1997 | liquid phase; ALS |
ΔrH° | -5.19 ± 0.38 | kcal/mol | Cm | Sola, Pericas, et al., 1997 | liquid phase; ALS |
By formula: Li+ + C4H8 = (Li+ • C4H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: C4H8 + HCl = C4H9Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15.08 ± 0.42 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochloronation; ALS |
By formula: C4H8 + H2O = C4H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.775 | kcal/mol | Eqk | Eberz and Lucas, 1934 | gas phase; solvent: Aqueous; Heat of hydration; ALS |
By formula: Na+ + C4H8 = (Na+ • C4H8)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
10.0 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
(CAS Reg. No. 38130-30-2 • 4294967295) + = CAS Reg. No. 38130-30-2
By formula: (CAS Reg. No. 38130-30-2 • 4294967295C4H8) + C4H8 = CAS Reg. No. 38130-30-2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.5 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
By formula: (C4H9 • 4294967295C4H8) + C4H8 = C4H9
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.3 ± 2.1 | kcal/mol | N/A | DePuy, Gronert, et al., 1989 | gas phase; B |
By formula: C5H12O = C4H8 + CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 9.51 ± 0.1 | kcal/mol | Cm | Arntz and Gottlieb, 1985 | gas phase; At 319K; ALS |
By formula: C4H8Br2 = C4H8 + Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33.40 ± 0.11 | kcal/mol | Cm | Sunner and Wulff, 1974 | liquid phase; ALS |
By formula: C4H8 + C4H10O = C8H18O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.01 ± 0.57 | kcal/mol | Eqk | Sharonov, Mishentseva, et al., 1991 | liquid phase; ALS |
By formula: C4H8 + C4H10O = C8H18O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.68 ± 0.43 | kcal/mol | Eqk | Sharonov, Mishentseva, et al., 1991 | liquid phase; ALS |
By formula: C4H8 + C4H10O = C8H18O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.32 ± 0.65 | kcal/mol | Eqk | Sharonov, Mishentseva, et al., 1991 | liquid phase; ALS |
By formula: C6H14O = C4H8 + C2H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.47 ± 0.46 | kcal/mol | Eqk | Sharonov, Rozhnov, et al., 1995 | liquid phase; ALS |
By formula: C4H9Br = C4H8 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.9 ± 0.9 | kcal/mol | Eqk | Kistiakowsky and Stauffer, 1937 | gas phase; ALS |
By formula: HBr + C4H8 = C4H9Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -18.850 | kcal/mol | Eqk | Howlett, 1957 | gas phase; ALS |
By formula: C4H8 + CH4O = C5H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.08 | kcal/mol | Cm | Sol, Perics, et al., 1994 | liquid phase; ALS |
By formula: C4H10O = C4H8 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.6 | kcal/mol | Eqk | Taft and Riesz, 1955 | liquid phase; ALS |
By formula: C7H8O + C4H8 = C11H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.0 ± 0.67 | kcal/mol | Eqk | Verevkin, Nesterova, et al., 1984 | gas phase; ALS |
By formula: C10H14O = C6H6O + C4H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.0 ± 0.50 | kcal/mol | Eqk | Verevkin, 1982 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes
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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C4H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.22 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 191.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 185.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
191.8 ± 1.1 | Bouchoux and Salpin, 1999 | T = 300K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM |
191.8 ± 1.1 | Bouchoux and Salpin, 1999 | T = 298K; MM |
192.4 ± 1.6 | Cleven, Hoke, et al., 1996 | PA > butyronitrile, < benzonitrile; MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
185.5 ± 0.65 | Bouchoux and Salpin, 1999 | T = 300K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM |
185.5 ± 0.65 | Bouchoux and Salpin, 1999 | T = 298K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.19 | PI | Traeger, 1986 | LBLHLM |
9.24 ± 0.05 | EI | Holmes and Lossing, 1983 | LBLHLM |
9.24 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.239 ± 0.003 | PE | Masclet, Grosjean, et al., 1973 | LLK |
9.19 | EI | Lossing, 1972 | LLK |
9.21 | PE | Frost and Sandhu, 1971 | LLK |
9.17 | PE | Dewar and Worley, 1969 | RDSH |
9.23 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.23 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.41 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
9.39 | PE | Koenig, Balle, et al., 1975 | Vertical value; LLK |
9.45 | PE | Kimura, Katsumata, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 16.4 | C3H5 | EI | SenSharma and Franklin, 1973 | LLK |
C2H4+ | 12.0 ± 0.25 | ? | EI | Meisels, Park, et al., 1970 | RDSH |
C3H5+ | 11.33 | CH3 | PI | Traeger, 1984 | LBLHLM |
C3H5+ | 11.8 | CH3 | EI | SenSharma and Franklin, 1973 | LLK |
C3H5+ | 11.45 | CH3 | EI | Lossing, 1972 | LLK |
C4H6+ | 11.3 ± 0.1 | H2 | EI | Holmes, Weese, et al., 1977 | LLK |
C4H7+ | 11.26 | H | PI | Traeger, 1986 | LBLHLM |
C4H7+ | 11.41 | H | EI | Lossing, 1972 | LLK |
De-protonation reactions
C4H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 393.0 ± 1.8 | kcal/mol | Endo | Wenthold, Hu, et al., 1999 | gas phase; B |
ΔrH° | 387.0 ± 2.0 | kcal/mol | D-EA | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrH° | 390.3 ± 2.3 | kcal/mol | G+TS | Bartmess and Burnham, 1984 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 385.6 ± 1.9 | kcal/mol | H-TS | Wenthold, Hu, et al., 1999 | gas phase; B |
ΔrG° | 379.6 ± 2.1 | kcal/mol | H-TS | Wenthold, Polak, et al., 1996 | gas phase; B |
ΔrG° | 382.9 ± 2.2 | kcal/mol | IMRE | Bartmess and Burnham, 1984 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D.,
Heats of combustion, formation, and insomerization of ten C4 hydrocarbons,
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Guinchant, 1918
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Etude sur la fonction acide dans les derives metheniques et methiniques,
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Stull D.R., 1969
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The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Todd S.S., 1936
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Kilpatrick J.E., 1946
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Heat content, free energy function, entropy, and heat capacity of ethylene, propylene, and the four butenes to 1500 K,
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East A.L.L., 1997
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Ab initio statistical thermodynamical models for the computation of third-law entropies,
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Scott R.B., 1945
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Photoelectron spectroscopy of the trimethylenemethane negative ion,
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Photoelectron Spectroscopy of the Allyl and 2-Methylallyl Anions,
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Effect of central substituents on the gas phase acidities of propenes,
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Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range,
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Ion Thermochemistry at High Temperatures. 1. Thermochemistry of the Ammonium Ion from Variable - Temperature Equilibrium Measurements. Proton Transfer, Association, and Decomposition Reactions in Ammonia, Isobutene, and t-Butylamine,
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The use of equilibrium constants to calculate thermodynamic quantities. Part II,
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Howlett, 1951
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The use of equilibrium constants to calculate thermodynamic quantities. Part I. Equilibria in the system tert.-butyl chloride, isobutene, hydrogen chloride,
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The kinetics of gaseous addition of halogen acids to isobutene, 1937, 165-170. [all data]
Sola, Pericas, et al., 1995
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Thermodynamic and kinetic studies of the liquid phase synthesis of tert-butyl ethyl ether using a reaction calorimeter,
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Equilibrium constant for ethyl tert-butyl ether vapor-phase synthesis,
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Li and Stone, 1989
Li, X.; Stone, J.A.,
Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes,
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Kistiakowsky, Ruhoff, et al., 1935
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Heats of organic reactions. II. Hydrogenation of some simpler olefinic hydrocarbons,
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Cox and Pilcher, 1970
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Benson and Amano, 1962
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Thermodynamic properties of tertiary iodides,
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Jones and Ogg, 1937
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The equilibrium (CH3)3CI = (CH3)2C = CH2 + HI,
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Equilibrium Constants for the liquid-phase synthesis of isopropyl tert-butyl ether from 2-propanol and isobutene,
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A comparative thermodynamic and kinetic study of the reaction between olefins and light alcohols leading to branced ethers. Reaction calorimetry study of the formation of tert-amyl methyl ether (TAME) and tert-butyl isopropyl ether (IPTBE),
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Staley and Beauchamp, 1975
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Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
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Dzidic and Kebarle, 1970
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Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
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Arnett and Pienta, 1980
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Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
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Eberz and Lucas, 1934
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The hydration of unsaturated compounds. II. The equilibrium between i-butene and t-butanol and the free energy of hydration of i-butene,
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Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions T Temperature ΔcH°gas Enthalpy of combustion of gas at standard conditions 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 ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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