Anisole
- Formula: C7H8O
- Molecular weight: 108.1378
- IUPAC Standard InChI: InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
- IUPAC Standard InChIKey: RDOXTESZEPMUJZ-UHFFFAOYSA-N
- CAS Registry Number: 100-66-3
- 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, methoxy-; Anizol; Methoxybenzene; Methyl phenyl ether; Phenyl methyl ether; Ether, methyl phenyl-; UN 2222; Phenoxymethane; Anisol; NSC 7920
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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -16.24 ± 0.29 | kcal/mol | Ccb | Fenwick, Harrop, et al., 1975 | Author was aware that data differs from previously reported values; ALS |
| ΔfH°gas | -18.33 ± 0.22 | kcal/mol | Ccb | Lebedeva and Katin, 1972 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -19.6 ± 0.3 kcal/mol; ALS |
| ΔfH°gas | -16.9 | kcal/mol | Ccb | Gray and Williams, 1959 | Private communication; ALS |
| ΔfH°gas | -17.9 | kcal/mol | N/A | Badoche, 1941 | Value computed using ΔfHliquid° value of -118.4 kj/mol from Badoche, 1941 and ΔvapH° value of 43.3 kj/mol from Lebedeva and Katin, 1972.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 38.829 | 388.15 | Hales J.L., 1967 | GT |
| 40.349 | 408.15 | ||
| 42.299 | 433.15 | ||
| 43.750 | 453.15 | ||
| 45.170 | 473.15 | ||
| 46.831 | 498.15 |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -27.43 ± 0.28 | kcal/mol | Ccb | Fenwick, Harrop, et al., 1975 | Author was aware that data differs from previously reported values; ALS |
| ΔfH°liquid | -28.7 ± 0.2 | kcal/mol | Ccb | Lebedeva and Katin, 1972 | ALS |
| ΔfH°liquid | -28.30 | kcal/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-31.02 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -904.187 | kcal/mol | Ccb | Fenwick, Harrop, et al., 1975 | Author was aware that data differs from previously reported values; Corresponding ΔfHºliquid = -27.431 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -902.9 ± 0.2 | kcal/mol | Ccb | Lebedeva and Katin, 1972 | Corresponding ΔfHºliquid = -28.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -903.32 | kcal/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-31.02 kcal/mol; Corresponding ΔfHºliquid = -28.30 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 47.56 | 298.15 | Fenwick, Harrop, et al., 1975, 2 | DH |
| 49.90 | 304.8 | Phillip, 1939 | DH |
| 45.70 | 297.2 | de Kolossowsky and Udowenko, 1933 | 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
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: Br- + C7H8O = (Br- • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.8 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 20. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 3.3 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 3.3 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 401.3 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-methoxyphenide and Me2NH.; B |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 398.3 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 391.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between HO- and m,p-methoxyphenide; B |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 401.7 ± 3.1 | kcal/mol | G+TS | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-OMe-phenide and Me2NH.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 394.0 ± 3.0 | kcal/mol | IMRB | Dahlke and Kass, 1992 | gas phase; Acid: anisole. Between o-OMe-phenide and Me2NH.; B |
+
= (
•
)
By formula: Cl- + C7H8O = (Cl- • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 7.30 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 7.3 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
+
=
+
By formula: HI + C7H7IO = C7H8O + I2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -6.9 ± 1.2 | kcal/mol | Cm | Brennan and Ubbelohde, 1956 | gas phase; ALS |
( •
) +
= (
• 2
)
By formula: (Li+ • C7H8O) + C7H8O = (Li+ • 2C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 29.0 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
( •
) +
= (
• 2
)
By formula: (Na+ • C7H8O) + C7H8O = (Na+ • 2C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 21.4 ± 0.6 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
( •
) +
= (
• 2
)
By formula: (Cs+ • C7H8O) + C7H8O = (Cs+ • 2C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.7 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
( •
) +
= (
• 2
)
By formula: (Rb+ • C7H8O) + C7H8O = (Rb+ • 2C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.2 ± 0.8 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
( •
) +
= (
• 2
)
By formula: (K+ • C7H8O) + C7H8O = (K+ • 2C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 16.7 ± 0.6 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
+
= (
•
)
By formula: Li+ + C7H8O = (Li+ • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 44.1 ± 4.5 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
+
= (
•
)
By formula: Na+ + C7H8O = (Na+ • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 27.1 ± 2.0 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
+
= (
•
)
By formula: Cs+ + C7H8O = (Cs+ • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.9 ± 1.2 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
+
= (
•
)
By formula: Rb+ + C7H8O = (Rb+ • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 17.3 ± 1.0 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
+
= (
•
)
By formula: K+ + C7H8O = (K+ • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 18.9 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2003 | RCD |
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.
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]
Lebedeva and Katin, 1972
Lebedeva, N.D.; Katin, Yu.A.,
Heats of combustion of certain monosubstituted benzenes,
Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 1088. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Gray and Williams, 1959
Gray, P.; Williams, A.,
Chemistry of free radicals containing oxygen. Part 3.- Thermochemistry and reactivity of the higher alkoxyl radicals RO·,
Trans. Faraday Soc., 1959, 55, 760-777. [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]
Hales J.L., 1967
Hales J.L.,
Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether,
Trans. Faraday Soc., 1967, 63, 1876-1879. [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]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]
de Kolossowsky and Udowenko, 1933
de Kolossowsky, N.A.; Udowenko, W.W.,
Mesure des chaleurs specifique moleculaires de quelques liquides,
Compt. rend., 1933, 197, 519-520. [all data]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [all data]
Dahlke and Kass, 1992
Dahlke, G.D.; Kass, S.R.,
The Ortho-dehydrophenoxy Anion,
Int. J. Mass Spectrom. Ion Proc., 1992, 117, 633, https://doi.org/10.1016/0168-1176(92)80117-J
. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Brennan and Ubbelohde, 1956
Brennan, D.; Ubbelohde, A.R.,
A thermochemical evaluation of bond strengths in some carbon compounds. Part IV. Bond-strength differences based on the reaction: RI + HI = RH + I2, where R = p-methoxyphenyl and cyclohexyl,
J. Chem. Soc., 1956, 3011-3016. [all data]
Amunugama and Rodgers, 2003
Amunugama, R.; Rodgers, M.T.,
Influence of substituents on cation-pi interactions - 5. Absolute binding energies of alkali metal cation-anisole complexes determined by threshold collision-induced dissociation and theoretical studies,
Int. J. Mass Spectrom., 2003, 222, 1-3, 431, https://doi.org/10.1016/S1387-3806(02)00945-4
. [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 T Temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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