α-Methylstyrene
- Formula: C9H10
- Molecular weight: 118.1757
- IUPAC Standard InChIKey: XYLMUPLGERFSHI-UHFFFAOYSA-N
- CAS Registry Number: 98-83-9
- 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: Benzene, (1-methylethenyl)-; Styrene, α-methyl-; α-Methylstyrol; β-Phenylpropylene; Isopropenylbenzene; 1-Methyl-1-phenylethylene; 1-Phenyl-1-methylethylene; 1-Propene, 2-phenyl-; 2-Phenyl-1-propene; 2-Phenylpropene; (1-Methylethenyl)benzene; AS-Methylphenylethylene; β-phenylpropene; α-Methylstyreen; α-Metil-stirolo; Isopropenil-benzolo; Isopropenyl-benzeen; Isopropenyl-benzol; 2-Phenylpropylene; UN 2303; Benzene, isopropenyl-; 2-Phenyl-2-propene; 1-Methyl-1-phenylethene; NSC 9400; a-methylstyrene
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Phase change 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 438. ± 4. | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 249.05 | K | N/A | Anonymous, 1952 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 247.22 | K | N/A | Anonymous, 1946 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 249.94 | K | N/A | Stull, 1945 | Uncertainty assigned by TRC = 0.25 K; TRC |
Tfus | 244.83 | K | N/A | Anonymous, 1943 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 645. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 35.04 | atm | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2.96 atm; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.44 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.13 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.7 ± 0.07 | kcal/mol | GS | Verevkin, 1999 | Based on data from 274. to 314. K.; AC |
ΔvapH° | 11.6 ± 0.1 | kcal/mol | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 331. to 467. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.8 ± 0.07 | 294. | GS | Verevkin, 1999 | Based on data from 274. to 314. K.; AC |
11.0 ± 0.07 | 340. | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 331. to 467. K.; AC |
10.3 ± 0.07 | 380. | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 331. to 467. K.; AC |
9.70 ± 0.07 | 420. | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 331. to 467. K.; AC |
9.0 ± 0.1 | 460. | EB | Steele, Chirico, et al., 1997, 2 | Based on data from 331. to 467. K.; AC |
10.6 | 358. | A | Stephenson and Malanowski, 1987 | Based on data from 343. to 493. K.; AC |
10.7 | 368. | A | Stephenson and Malanowski, 1987 | Based on data from 353. to 413. 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 |
---|---|---|---|---|---|
280.6 to 438.6 | 5.21396 | 2326.867 | 7.23 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.8499 | 250.78 | Lebedev and Rabinovich, 1971 | DH |
2.849 | 250.8 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.36 | 250.78 | Lebedev and Rabinovich, 1971 | DH |
Reaction 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
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
By formula: HCl + C9H10 = C9H11Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.80 ± 0.45 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination; ALS |
ΔrH° | -12.4 ± 1.1 | kcal/mol | Cm | Nesterova, Kovzel, et al., 1977 | liquid phase; Hydrochlorination; ALS |
C9H9- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 385.6 ± 5.6 | kcal/mol | G+TS | Bartmess and Burnham, 1984 | gas phase; between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 379.0 ± 5.5 | kcal/mol | IMRB | Bartmess and Burnham, 1984 | gas phase; between H2O, MeOH; B |
By formula: H2 + C9H10 = C9H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -26.60 ± 0.50 | kcal/mol | Chyd | Abboud, Jimenez, et al., 1995 | liquid phase; solvent: Hyrocarbon; Like gas phase; ALS |
By formula: HBr + C9H10 = C9H11Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15.2 ± 1.3 | kcal/mol | Cm | Nesterova, Kovzel, et al., 1977 | liquid phase; Hydrobromination; ALS |
Gas phase ion energetics data
Go To: Top, Phase change 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
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 C9H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 206.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 199.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.3 ± 0.1 | EI | Koppel, Schwarz, et al., 1974 | LLK |
8.18 ± 0.04 | EI | Benito, Seidl, et al., 1973 | LLK |
8.35 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.50 | PE | Chizhov, Timoshenko, et al., 1986 | Vertical value; LBLHLM |
8.52 | PE | Kobayashi, Yokota, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H9+ | 11.8 ± 0.1 | H | EI | Koppel, Schwarz, et al., 1974 | LLK |
De-protonation reactions
C9H9- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 385.6 ± 5.6 | kcal/mol | G+TS | Bartmess and Burnham, 1984 | gas phase; between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 379.0 ± 5.5 | kcal/mol | IMRB | Bartmess and Burnham, 1984 | gas phase; between H2O, MeOH; B |
References
Go To: Top, Phase change 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.
Anonymous, 1952
Anonymous, R.,
, Physical Properties of Chemical Substances, Dow Chemical Co., 1952. [all data]
Anonymous, 1946
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1946. [all data]
Stull, 1945
Stull, D.R.,
Personal Commun., Dow Chemical Co., 1945. [all data]
Anonymous, 1943
Anonymous, R.,
, Sunbury Rep. No. 2176, Anglo-Iranian Oil Co., 1943. [all data]
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturated Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Trimethyl benzene, Pentafluorophenol, 4-tert-Butylcatechol, .alp,
J. Chem. Eng. Data, 1997, 42, 1008-20. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemical investigation on α-methyl-styrene and parent phenyl substituted alkenes,
Thermochimica Acta, 1999, 326, 1-2, 17-25, https://doi.org/10.1016/S0040-6031(98)00585-1
. [all data]
Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Triethylbenzene, Pentafluorophenol, 4- tert -Butylcatechol, α-Methylstyrene, and N , N '-Bis(2-hydroxyethyl)ethylenediamine,
J. Chem. Eng. Data, 1997, 42, 6, 1008-1020, https://doi.org/10.1021/je970102d
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Lebedev and Rabinovich, 1971
Lebedev, B.V.; Rabinovich, I.B.,
Heat capacities and thermodynamic functions of a-methylstyrene and poly(a-methylstyrene),
Tr. Khim. Khim. Tekhnol., 1971, 1, 12-15. [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]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]
Nesterova, Kovzel, et al., 1977
Nesterova, T.N.; Kovzel, E.N.; Karaseva, S.Ya.; Rozhnov, A.M.,
Heats of reaction of the hydrohalogenation of styrene and α-methylstyrene,
Vses. Konf. Kalorim. Rasshir. Tezisy Dokl. 7th, 1977, 1, 132. [all data]
Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R.,
Effect of central substituents on the gas phase acidities of propenes,
J. Org. Chem., 1984, 49, 1382. [all data]
Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F.,
Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-β- and β,β-methylated derivates,
J. Phys. Org. Chem., 1995, 8, 15-25. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F.,
Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VIII. Struktur der stabilen und instabilen ionen[C9H9]+ aus isomeren C9H10- kohlenwasserstoffen,
Org. Mass Spectrom., 1974, 8, 25. [all data]
Benito, Seidl, et al., 1973
Benito, I.; Seidl, H.; Bock, H.,
Efectos electronicos y estericos de sustituyentes alquilicos y silicicos sobre el sistema electronico π del estireno,
Rev. Fac. Cienc. Univ. Oviedo, 1973, 14, 95. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Chizhov, Timoshenko, et al., 1986
Chizhov, Y.V.; Timoshenko, M.M.; Kleimenov, V.I.; Borisov, Y.A.; Zol'nikova, G.P.; Kravtsov, D.N.; Kritskaya, I.I.,
Investigation of the mechanism of fragment coordination of aromatic molecules with transition metals by photoelectron spectroscopy - tricarbonyliron complexes,
J. Struct. Chem., 1986, 27, 401. [all data]
Kobayashi, Yokota, et al., 1973
Kobayashi, T.; Yokota, K.; Nagakura, S.,
Photoelectron spectra of styrenes,
J. Electron Spectrosc. Relat. Phenom., 1973, 3, 449. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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