Benzene, ethoxy-

Formula: C₈H₁₀O
Molecular weight: 122.1644
IUPAC Standard InChI: InChI=1S/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
IUPAC Standard InChIKey: DLRJIFUOBPOJNS-UHFFFAOYSA-N
CAS Registry Number: 103-73-1
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Phenetole; Ethoxybenzene; Ethyl phenyl ether; Phenyl ethyl ether; Ether, ethyl phenyl-; Phenoxyethane; Benzyl methyl ether
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Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-36.48 ± 0.28	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_fH°_liquid	-38.10	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1057.50	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_liquid = -36.482 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1055.89	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; Corresponding Δ_fHº_liquid = -38.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
54.61	298.15	Fenwick, Harrop, et al., 1975, 2	DH

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, References, Notes

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

View reactions leading to C₈H₁₀O⁺ (ion structure unspecified)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.6	EI	Williams, Cooks, et al., 1968	RDSH
8.13 ± 0.02	PI	Watanabe, Nakayama, et al., 1962	RDSH
8.36	PE	Friege and Klessinger, 1979	Vertical value; LLK
8.41	PE	Dewar, Ernstbrunner, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₆H₆O⁺	10.03 ± 0.19	C₂H₄	EI	Bouchoux, 1978	LLK
C₆H₆O⁺	11.3	C₂H₄	EI	Williams, Cooks, et al., 1968	RDSH
C₆H₆O⁺	10.73	C₂H₄	EI	Gillis, Long, et al., 1968	RDSH

References

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Fenwick, Harrop, et al., 1975
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodyn., 1975, 7, 943-954. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Fenwick, Harrop, et al., 1975, 2
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodynam., 1975, 7, 944-954. [all data]

Williams, Cooks, et al., 1968
Williams, D.H.; Cooks, R.G.; Howe, I., Studies in mass spectrometry. XXXI. A comparison of reaction rates in common ions generated via fragmentation and direct ionization, J. Am. Chem. Soc., 1968, 90, 6759. [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]

Friege and Klessinger, 1979
Friege, H.; Klessinger, M., Elektronenstruktur von Alkyl-aryl- und Alkyl-vinyl-ethern, Chem. Ber., 1979, 112, 1614. [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]

Bouchoux, 1978
Bouchoux, G., Ionisation et fragmentation en spectrometrie de masse, Org. Mass Spectrom., 1978, 13, 184. [all data]

Gillis, Long, et al., 1968
Gillis, R.G.; Long, G.J.; Moritz, A.G.; Occolowitz, J.L., Energetics of the electron-impact fragmentation of alkoxybenzenes and alkylthiobenzenes, Org. Mass Spectrom., 1968, 1, 527. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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