Benzene, 1,2-dimethoxy-
- Formula: C8H10O2
- Molecular weight: 138.1638
- IUPAC Standard InChI: InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
- IUPAC Standard InChIKey: ABDKAPXRBAPSQN-UHFFFAOYSA-N
- CAS Registry Number: 91-16-7
- 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: Benzene, o-dimethoxy-; o-Dimethoxybenzene; O,O-Dimethyl catechol; Pyrocatechol dimethyl ether; Veratrol; Veratrole; 1,2-Dimethoxybenzene; Dimethylether pyrokatechinu; Orthodimethoxybenzene; 2-Methoxyanisole; Catechol dimethyl ether; NSC 16934; Methylguaiacol; 1,2-Dimethoxybenzene (veratroI); 1,2-Dimethoxybenzene (veratrole); 1,2-Dimethoxybenzene (Veratrol)
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Condensed phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -4286.9 ± 2.1 | kJ/mol | Ccb | Cass, Fletcher, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -4284. ± 2. kJ/mol; Corresponding ΔfHºliquid = -290.3 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 7.8 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.8 | PE | Domelsmith and Houk, 1978 | LLK |
| 7.8 ± 0.15 | CTS | Voigt and Reid, 1964 | RDSH |
| 8.17 | PE | Anderson, Kollman, et al., 1979 | Vertical value; LLK |
| 7.8 | PE | Domelsmith and Houk, 1978 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H5+ | 12.7 | CH3+CO+H2O | EI | Mori, Ogawa, et al., 1992 | LL |
| C6H7O+ | 12.2 | CH3+CO | EI | Mori, Ogawa, et al., 1992 | LL |
References
Go To: Top, Condensed phase 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.
Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D.,
Heats of combustion and molecular structure. Part VI. The structure of some cyclic ethers of o-dihydroxybenzene,
J. Chem. Soc., 1958, 2595-2597. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Domelsmith and Houk, 1978
Domelsmith, L.N.; Houk, K.N.,
Photoelectron spectroscopic studies of hallucinogens: The use of ionization potentials in QSAR,
NIDA Res. Monogr., 1978, 22, 423. [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]
Anderson, Kollman, et al., 1979
Anderson, G.M., III; Kollman, P.A.; Domelsmith, L.N.; Houk, K.N.,
Methoxy group nonplanarity in o-dimethoxybenzenes. Simple predictive models for conformations and rotational barriers in alkoxyaromatics,
J. Am. Chem. Soc., 1979, 101, 2344. [all data]
Mori, Ogawa, et al., 1992
Mori, Y.; Ogawa, Y.; Shinoda, H.; Kitagawa, T.,
Two competing fragmentation processes in dimethoxybenzenes depending on their positional isomers: Elimination of CH3 and CHnO (n = 1-3) and formation of methoxycyclopentadienyl and protonated phenol ions,
Org. Mass Spectrom., 1992, 27, 578. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔcH°liquid Enthalpy of combustion of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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