Benzyl sulfone
- Formula: C14H14O2S
- Molecular weight: 246.325
- IUPAC Standard InChI: InChI=1S/C14H14O2S/c15-17(16,11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2
- IUPAC Standard InChIKey: AWHNUHMUCGRKRA-UHFFFAOYSA-N
- CAS Registry Number: 620-32-6
- 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: Dibenzyl sulfone; Benzene, 1,1'-[sulfonylbis(methylene)]bis-; Dibenzyl sulphone
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Gas phase thermochemistry data
Go To: Top, Condensed 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -157.1 ± 3.2 | kJ/mol | Ccr | Mackle and O'Hare, 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -151. ± 3. kJ/mol; Haet of combustion corrected for pressure |
Condensed phase thermochemistry 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -282.6 ± 1.2 | kJ/mol | Ccr | Mackle and O'Hare, 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -265. ± 0.8 kJ/mol; Haet of combustion corrected for pressure |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -7829.6 ± 1.0 | kJ/mol | Ccr | Mackle and O'Hare, 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -7847.3 ± 0.2 kJ/mol; Haet of combustion corrected for pressure |
Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 422.7 | K | N/A | Kaldor and Hammond, 1991 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 425. | K | N/A | Jarvis, Hoey, et al., 1988 | Uncertainty assigned by TRC = 3. K; TRC |
| Tfus | 402. | K | N/A | Olah and Gupta, 1983 | Uncertainty assigned by TRC = 2. K; TRC |
| Tfus | 425. | K | N/A | Boehme and Sitorus, 1972 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 114. ± 2. | kJ/mol | V | Mackle and O'Hare, 1961 | Haet of combustion corrected for pressure; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Mackle and O'Hare, 1961
Mackle, H.; O'Hare, P.A.G.,
Studies in the thermochemistry of sulphones. Part 6 - Heats of combustion, fusion, vaporization and atomization of six aromatic and two allylic sulphones,
Trans. Faraday Soc., 1961, 57, 1521-1526. [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]
Kaldor and Hammond, 1991
Kaldor, S.W.; Hammond, M.,
A Mild Osmium Tetraoxide-Catalyzed Method for the Oxidation of Sulfides to Sulfones,
Tetrahedron Lett., 1991, 32, 5043-6. [all data]
Jarvis, Hoey, et al., 1988
Jarvis, W.T.; Hoey, M.D.; Finocchio, A.L.; Dittmar, D.C.,
Organic reactions of Reduced Species of Sulfur Dioxide,
J. Org. Chem., 1988, 53, 5750-6. [all data]
Olah and Gupta, 1983
Olah, G.A.; Gupta, B.G.B.,
Onium Ions 27. Oxidation of Sulfoxides to Sulfones with Nitronium Salts,
J. Org. Chem., 1983, 48, 3585-7. [all data]
Boehme and Sitorus, 1972
Boehme, V.H.; Sitorus, U.,
Oxidation of Thioethers to Sulfones with Hydrogen Peroxide in Alkaline Solution,
Chem.-Ztg., 1972, 96, 37-8. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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