Dibenzo-18-crown-6
- Formula: C20H24O6
- Molecular weight: 360.4010
- IUPAC Standard InChIKey: YSSSPARMOAYJTE-UHFFFAOYSA-N
- CAS Registry Number: 14187-32-7
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-; Dibenzo-18-crown-6-ether; Crown 18; Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecane; Crown ether dibenzo-18-crown-6; 6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin; 2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane; NSC 147771; dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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 |
---|---|---|---|---|---|
ΔfH°solid | -822.4 ± 2.4 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1992 | Authors Hf298_condensed=-787.7±2.4 kJ/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -10477.8 ± 4.8 | kJ/mol | Ccb | Vasil'ev, Borodin, et al., 1992 | Authors Hf298_condensed=-787.7±2.4 kJ/mol; Corresponding ΔfHºsolid = -822.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
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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
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 435. | K | N/A | Solov'ev, Govorkova, et al., 1986 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 434. | K | N/A | Biancheria, Giusti, et al., 1985 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 137.0 ± 7.4 | kJ/mol | CGC | Nichols, Orf, et al., 2000 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 178.8 ± 6.9 | kJ/mol | CGC-DSC | Nichols, Orf, et al., 2000 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
57.45 | 435.8 | Domanska, 1998 | AC |
Gas phase ion energetics 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 as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.6 | PE | Baker, Armen, et al., 1983 | LBLHLM |
7.8 | PE | Baker, Armen, et al., 1983 | Vertical value; LBLHLM |
7.70 | PE | Kajitani, Sugimori, et al., 1979 | Vertical value; LLK |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Vasil'ev, Borodin, et al., 1992
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B.,
Standard enthalpies of formation of certain crown-ethers,
Russ. J. Phys. Chem. (Engl. Transl.), 1992, 66, 585-587, In original 1104. [all data]
Solov'ev, Govorkova, et al., 1986
Solov'ev, V.P.; Govorkova, L.V.; Raevskii, O.A.,
Determination of the Purity, Melting Point and Heat of Melting of Cyclic Polyethers,
Izv. Akad. Nauk SSSR, Ser. Khim., 1986, No. 3, 691-2. [all data]
Biancheria, Giusti, et al., 1985
Biancheria, A.; Giusti, J.; Paoletti, P.,
Analysis by DSC of the KNCS/dibenzo-18-crown-6 system: phase diagram and enthalpy changes,
Thermochim. Acta, 1985, 90, 109. [all data]
Nichols, Orf, et al., 2000
Nichols, Gary; Orf, Jennifer; Reiter, Sarah M.; Chickos, James; Gokel, George W.,
The vaporization enthalpies of some crown and polyethers by correlation gas chromatography,
Thermochimica Acta, 2000, 346, 1-2, 15-28, https://doi.org/10.1016/S0040-6031(99)00405-0
. [all data]
Domanska, 1998
Domanska, U.,
Measurement and correlation of the solubility of crown ethers in selected organic solvents,
Pol. J. Chem., 1998, 72, 5, 925. [all data]
Baker, Armen, et al., 1983
Baker, A.D.; Armen, G.H.; Funaro, S.,
Oral levels of crown ethers and related macrocycles studies by ultraviolet photoelectron spectroscopy: Relationship to complexation studies,
J. Chem. Soc. Dalton Trans., 1983, 2519. [all data]
Kajitani, Sugimori, et al., 1979
Kajitani, M.; Sugimori, A.; Sato, N.; Seki, K.; Inokuchi, H.; Harada, Y.,
Ultraviolet photoelectron spectra of crown ethers,
Bull. Chem. Soc. Jpn., 1979, 52, 2199. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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