12-Crown-4
- Formula: C8H16O4
- Molecular weight: 176.2102
- IUPAC Standard InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N
- CAS Registry Number: 294-93-9
- 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: 1,4,7,10-Tetraoxacyclododecane; 12-Crown-4 ether; Eoct; Ethylene oxide cyclic tetramer
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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 | -631.1 ± 2.1 | kJ/mol | Ccr | Bystrm and Mansson, 1982 |
Condensed phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -696.8 ± 2.1 | kJ/mol | Ccr | Bystrm and Mansson, 1982 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4738.1 ± 1.7 | kJ/mol | Ccr | Bystrm and Mansson, 1982 | Corresponding ΔfHºliquid = -696.65 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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔvapH° | 65.7 ± 3.7 | kJ/mol | CGC | Nichols, Orf, et al., 2000 | AC |
ΔvapH° | 65.65 ± 0.37 | kJ/mol | C | Bystrm and Mansson, 1982 | ALS |
ΔvapH° | 65.7 | kJ/mol | N/A | Bystrm and Mansson, 1982 | DRB |
ΔvapH° | 65.6 ± 0.4 | kJ/mol | C | Bystr«65533»m and M«65533»nsson, 1982 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.46 | 290.7 | Domanska, 1998 | AC |
Reaction thermochemistry 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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: C3H10N+ + C8H16O4 = (C3H10N+ • C8H16O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 150. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 174. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: C4H5N2+ + C8H16O4 = (C4H5N2+ • C8H16O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 155. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 171. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: C5H6N+ + C8H16O4 = (C5H6N+ • C8H16O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 151. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 167. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: C6H14N+ + C8H16O4 = (C6H14N+ • C8H16O4)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 156. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 146. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: Na+ + C8H16O4 = (Na+ • C8H16O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372. ± 51. | kJ/mol | CIDT | More, Ray, et al., 1997 | RCD |
By formula: Li+ + C8H16O4 = (Li+ • C8H16O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 252. ± 13. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: Cs+ + C8H16O4 = (Cs+ • C8H16O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 84.9 ± 9.2 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: Rb+ + C8H16O4 = (Rb+ • C8H16O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 93. ± 13. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: K+ + C8H16O4 = (K+ • C8H16O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 189. ± 12. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 927.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 890.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.8 | PE | Baker, Armen, et al., 1983 | LBLHLM |
9.3 | PE | Baker, Armen, et al., 1983 | Vertical value; LBLHLM |
9.3 | PE | Kajitani, Sugimori, et al., 1979 | Vertical value; LLK |
IR Spectrum
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118817 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bystrm and Mansson, 1982
Bystrm, K.; Mansson, M.,
Enthalpies of formation of some cyclic 1,3- and 1,4-Di- and poly-ethers: Thermochemical strain in the -O-C-O and -O-C-C-O- groups,
J. Chem. Soc. Perkin Trans. 2, 1982, 565. [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]
Bystr«65533»m and M«65533»nsson, 1982
Bystr«65533»m, Katarina; M«65533»nsson, Margret,
Enthalpies of formation of some cyclic 1,3- and 1,4-di- and poly-ethers: thermochemical strain in the ?O?C?O? and ?O?C?C?O? groups,
J. Chem. Soc., Perkin Trans. 2, 1982, 5, 565, https://doi.org/10.1039/p29820000565
. [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]
Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M.,
The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers,
J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012
. [all data]
More, Ray, et al., 1997
More, M.B.; Ray, D.; Armentrout, P.B.,
Cation-ether complexes in the gas phase: Bond dissociation energies of Na+(dimethyl ether)(x), x=1-4; Na+(1,2-dimethoxyethane)(x), x=1 and 2; and Na+(12-crown-4),
J. Phys. Chem. AJOURNAL OF PHYSICAL CHEMISTRY A 101 (5): 831-839 JAN 30 1997, 1997, 101, 831. [all data]
Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B.,
Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation,
Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
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 ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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