α-Methylstyrene
- Formula: C9H10
- Molecular weight: 118.1757
- IUPAC Standard InChI: InChI=1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3
- 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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Gas phase thermochemistry data
Go To: Top, Condensed 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 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 | 28.27 ± 0.34 | kcal/mol | Eqk | Guthrie, 1978 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°gas | -1215.05 | kcal/mol | Ccb | Krall and Roberts, 1958 | Corresponding ΔfHºgas = 27.01 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.88 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
| 13.72 | 100. | ||
| 17.63 | 150. | ||
| 22.50 | 200. | ||
| 30.679 | 273.15 | ||
| 33.578 | 298.15 | ||
| 33.791 | 300. | ||
| 44.857 | 400. | ||
| 54.271 | 500. | ||
| 61.93 | 600. | ||
| 68.14 | 700. | ||
| 73.26 | 800. | ||
| 77.51 | 900. | ||
| 81.09 | 1000. | ||
| 84.13 | 1100. | ||
| 86.69 | 1200. | ||
| 88.89 | 1300. | ||
| 90.77 | 1400. | ||
| 92.38 | 1500. |
Condensed phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -1204.87 | kcal/mol | Ccb | Roberts and Jessup, 1951 | Corresponding ΔfHºliquid = 16.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1217.3 | kcal/mol | Ccb | Lemoult, 1911 | Corresponding ΔfHºliquid = 29.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1195.1 | kcal/mol | Ccb | Auwsers, Roth, et al., 1910 | Corresponding ΔfHºliquid = 7.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 58.27 | cal/mol*K | N/A | Lebedev and Rabinovich, 1971 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 48.33 | 300. | Lebedev and Rabinovich, 1971 | T = 60 to 300 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Guthrie, 1978
Guthrie, J.P.,
Equilibrium constants for a series of simple aldol condensations, and linear free energy relations with other carbonyl addition reactions,
Can. J. Chem., 1978, 56, 962-973. [all data]
Krall and Roberts, 1958
Krall, R.E.; Roberts, J.D.,
Strain variation in the unsaturated cyclobutane ring,
Am. Chem. Soc. Div. Pet. Chem., 1958, 3, 63-68. [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]
Roberts and Jessup, 1951
Roberts, D.E.; Jessup, R.S.,
Heat of polymerization of alpha-methylstyrene from heats of combustion of monomer and four polymer fractions,
J. Res. NBS, 1951, 46, 11-17. [all data]
Lemoult, 1911
Lemoult, M.P.,
Thermochimie. - Recherches sur les derives du styrolene; rectification de quelques erreurs experimentales,
Compt. Rend., 1911, 152, 1402-1404. [all data]
Auwsers, Roth, et al., 1910
Auwsers, K.; Roth, W.A.; Eisenlohr, F.,
III. Verbrennungswarmen von Terpenen und Styrolen,
Justus Liebigs Ann. Chem., 1910, 267-290. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔcH°liquid Enthalpy of combustion of liquid 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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