Anisole
- Formula: C7H8O
- Molecular weight: 108.1378
- 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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Reaction thermochemistry data
Go To: Top, 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 |
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 |
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 |
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 |
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 |
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, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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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