Benzene, 1-methoxy-4-methyl-
- Formula: C8H10O
- Molecular weight: 122.1644
- IUPAC Standard InChI: InChI=1S/C8H10O/c1-7-3-5-8(9-2)6-4-7/h3-6H,1-2H3
- IUPAC Standard InChIKey: CHLICZRVGGXEOD-UHFFFAOYSA-N
- CAS Registry Number: 104-93-8
- 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: Anisole, p-methyl-; p-Cresol methyl ether; p-Methoxytoluene; p-Methylanisole; p-Tolyl methyl ether; Methyl p-tolyl ether; 1-Methoxy-4-methylbenzene; 4-Methoxytoluene; 4-Methylanisole; p-Cresyl methyl ether; Methyl p-cresyl ether; Methyl 4-methylphenyl ether; 1-Methyl-4-methoxybenzene; 4-Methyl-1-methoxybenzene; 4-Methylphenol methyl ether; Methyl p-methylphenyl ether; 4-Methylmethoxybenzene; para-Methyl anisol; para-Methyl anisole; p-Methylanisol; NSC 6254; 4-Methylanisol
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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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 12.65 | 100. | Sharma S.N., 1982 | Estimations by difference method [ Dorofeeva O.V., 1997] have reason to suppose that Cp(298.15 K) and S(298.15 K) values obtained by [83SHA3] may be underestimated by 10-25 J/mol*K. |
| 23.14 | 200. | ||
| 33.810 | 300. | ||
| 44.345 | 400. | ||
| 53.623 | 500. | ||
| 61.362 | 600. | ||
| 67.763 | 700. | ||
| 73.098 | 800. | ||
| 77.579 | 900. | ||
| 81.372 | 1000. | ||
| 84.598 | 1100. | ||
| 87.352 | 1200. | ||
| 89.716 | 1300. | ||
| 91.747 | 1400. | ||
| 93.504 | 1500. | ||
| 95.026 | 1600. | ||
| 96.353 | 1700. | ||
| 97.514 | 1800. | ||
| 98.533 | 1900. | ||
| 99.431 | 2000. |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 447.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 450.9 | K | N/A | Ogimachi, Andrews, et al., 1955 | Uncertainty assigned by TRC = 3. K; TRC |
| Tboil | 449.9 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tboil | 449.7 | K | N/A | Boord, Greenlee, et al., 1945 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Tboil | 443.75 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 241.10 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tfus | 241.96 | K | N/A | Boord, Greenlee, et al., 1945 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tc | 666. | K | N/A | Young, 1994 | Uncertainty assigned by TRC = 1. K; TRC |
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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
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 C8H10O+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 7.90 ± 0.05 | eV | N/A | N/A | L |
Proton affinity at 298K
| Proton affinity (kcal/mol) | Reference | Comment |
|---|---|---|
| 201. ± 2. | van Beelen, Koblenz, et al., 2004 | T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM |
Gas basicity at 298K
| Gas basicity (review) (kcal/mol) | Reference | Comment |
|---|---|---|
| 193. ± 2. | van Beelen, Koblenz, et al., 2004 | T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.90 ± 0.03 | PI | Ponomarev, Arapov, et al., 1986 | LBLHLM |
| 7.85 | EI | Cooks, Bertrand, et al., 1973 | LLK |
| 7.91 | CTS | Pitt, Carey, et al., 1972 | LLK |
| 7.83 | EI | Hoffman and Bursey, 1971 | LLK |
| 8.3 ± 0.1 | EI | Brown, 1970 | RDSH |
| 8.0 ± 0.15 | CTS | Voigt and Reid, 1964 | RDSH |
| 8.14 ± 0.01 | PE | Bernardi, Distefano, et al., 1975 | Vertical value; LLK |
| 8.18 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
| 8.17 | PE | Eaton and Traylor, 1974 | Vertical value; LLK |
| 8.16 | PE | Dewar, Ernstbrunner, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H7+ | 12.9 | ? | EI | Harrison, Haynes, et al., 1965 | RDSH |
| C7H7+ | 12.59 | ? | EI | Hoffman and Bursey, 1971 | LLK |
| C7H7O+ | 11.36 ± 0.05 | CH3 | PI | Ponomarev, Arapov, et al., 1986 | LBLHLM |
| C7H7O+ | 11.5 ± 0.1 | CH3 | EI | Brown, 1970 | RDSH |
| C7H7O+ | 10.8 ± 0.1 | CH3 | EI | Tait, Shannon, et al., 1962 | RDSH |
| C7H8+ | 11.23 | HCHO | EI | Cooks, Bertrand, et al., 1973 | LLK |
| C7H8+ | 11.1 ± 0.1 | CH2O | EI | Brown, 1970 | RDSH |
| C8H9O+ | 11.91 | H | EI | Hoffman and Bursey, 1971 | LLK |
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.
Sharma S.N., 1982
Sharma S.N.,
Infrared and laser Raman spectra of m- and p-methylanisoles,
Acta Phys. Pol., 1982, A62, 449-456. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Ogimachi, Andrews, et al., 1955
Ogimachi, N.N.; Andrews, L.J.; Keefer, R.M.,
The Free Energies and Heats of Formation of Polyalkoxybenzene-Iodine Monochloride Complexes,
J. Am. Chem. Soc., 1955, 77, 4202. [all data]
Olson, Hipsher, et al., 1947
Olson, W.T.; Hipsher, H.F.; Buess, C.M.; Goodman, I.A.; Hart, I.; Lamneck, J.H.; Gibbons, L.C.,
The Synthesis and Purification of Ethers,
J. Am. Chem. Soc., 1947, 69, 2451-4. [all data]
Boord, Greenlee, et al., 1945
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.,
, Am. Pet. Inst. Res. Proj. 45, Seventh Annu. Rep., Ohio State Univ., June 30, 1945. [all data]
Perkin, 1896
Perkin, W.H.,
LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds,
J. Chem. Soc., 1896, 69, 1025-1257. [all data]
Young, 1994
Young, C.L.,
Personal Commun. 1994 1994, 1994. [all data]
van Beelen, Koblenz, et al., 2004
van Beelen, E.S.E.; Koblenz, T.A.; Ingemann, S.; Hammerum, S.,
Experimental and theoretical evaluation of proton affinities of furan, the methylphenols, and the related anisoles,
J. Phys. Chem. A, 2004, 108, 2787. [all data]
Ponomarev, Arapov, et al., 1986
Ponomarev, D.A.; Arapov, O.V.; Sergeev, Y.L.; Chistyakov, A.B.,
[Title unavailable],
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1986, 29, 107. [all data]
Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W.,
Energy partitioning data as an ion structure probe. Substituted anisoles,
J. Am. Chem. Soc., 1973, 95, 1732. [all data]
Pitt, Carey, et al., 1972
Pitt, C.G.; Carey, R.N.; Toren, E.C.,
Nature of the electronic interactions in aryl-substituted polysilanes,
J. Am. Chem. Soc., 1972, 94, 3806. [all data]
Hoffman and Bursey, 1971
Hoffman, M.K.; Bursey, M.M.,
Structural characteristics of non-decomposing C7H7+ ions from some methyl ethers on electron impact,
Chem. Commun., 1971, 824. [all data]
Brown, 1970
Brown, P.,
Kinetic studies in mass spectrometry. VIII. Competing [M-CH3] and [M-CH2O] reactions in substituted anisoles. Approximate activation energies from ionization appearance potentials,
Org. Mass Spectrom., 1970, 4, 519. [all data]
Voigt and Reid, 1964
Voigt, E.M.; Reid, C.,
Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene,
J. Am. Chem. Soc., 1964, 86, 3930. [all data]
Bernardi, Distefano, et al., 1975
Bernardi, F.; Distefano, G.; Mangini, A.; Pignataro, S.; Spunta, G.,
Photoelectron spectra of substituted anisoles thioanisoles,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 457. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G.,
Distortional stabilization in phenyl participations,
J. Am. Chem. Soc., 1974, 96, 7109. [all data]
Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M.,
Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy,
Tetrahedron, 1974, 30, 2455. [all data]
Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F.,
The mass spectra of methyl-substituted cyclopentadienes,
J. Am. Chem. Soc., 1965, 87, 5099. [all data]
Tait, Shannon, et al., 1962
Tait, J.M.S.; Shannon, T.W.; Harrison, A.G.,
The structure of substituted C7 ions from benzyl derivatives at the appearance potential threshold,
J. Am. Chem. Soc., 1962, 84, 4. [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 IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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