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12-Crown-4

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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, Ion clustering 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
Deltafgas-631.1 ± 2.1kJ/molCcrBystrm 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
Deltafliquid-696.8 ± 2.1kJ/molCcrBystrm and Mansson, 1982 
Quantity Value Units Method Reference Comment
Deltacliquid-4738.1 ± 1.7kJ/molCcrBystrm and Mansson, 1982Corresponding «DELTA»fliquid = -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
Deltavap65.7 ± 3.7kJ/molCGCNichols, Orf, et al., 2000AC
Deltavap65.65 ± 0.37kJ/molCBystrm and Mansson, 1982ALS
Deltavap65.7kJ/molN/ABystrm and Mansson, 1982DRB
Deltavap65.6 ± 0.4kJ/molCBystr«65533»m and M«65533»nsson, 1982AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
22.46290.7Domanska, 1998AC

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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 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

C3H10N+ + 12-Crown-4 = (C3H10N+ bullet 12-Crown-4)

By formula: C3H10N+ + C8H16O4 = (C3H10N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar150.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar174.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C4H5N2+ + 12-Crown-4 = (C4H5N2+ bullet 12-Crown-4)

By formula: C4H5N2+ + C8H16O4 = (C4H5N2+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar155.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar171.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C5H6N+ + 12-Crown-4 = (C5H6N+ bullet 12-Crown-4)

By formula: C5H6N+ + C8H16O4 = (C5H6N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar151.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar167.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C6H14N+ + 12-Crown-4 = (C6H14N+ bullet 12-Crown-4)

By formula: C6H14N+ + C8H16O4 = (C6H14N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar156.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar146.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

Sodium ion (1+) + 12-Crown-4 = (Sodium ion (1+) bullet 12-Crown-4)

By formula: Na+ + C8H16O4 = (Na+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar372. ± 51.kJ/molCIDTMore, Ray, et al., 1997RCD

Lithium ion (1+) + 12-Crown-4 = (Lithium ion (1+) bullet 12-Crown-4)

By formula: Li+ + C8H16O4 = (Li+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar252. ± 13.kJ/molCIDTRodgers and Armentrout, 2000RCD

Cesium ion (1+) + 12-Crown-4 = (Cesium ion (1+) bullet 12-Crown-4)

By formula: Cs+ + C8H16O4 = (Cs+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar84.9 ± 9.2kJ/molCIDTRodgers and Armentrout, 2000RCD

Rubidium ion (1+) + 12-Crown-4 = (Rubidium ion (1+) bullet 12-Crown-4)

By formula: Rb+ + C8H16O4 = (Rb+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar93. ± 13.kJ/molCIDTRodgers and Armentrout, 2000RCD

Potassium ion (1+) + 12-Crown-4 = (Potassium ion (1+) bullet 12-Crown-4)

By formula: K+ + C8H16O4 = (K+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar189. ± 12.kJ/molCIDTRodgers and Armentrout, 2000RCD

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering 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)927.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity890.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.8PEBaker, Armen, et al., 1983LBLHLM
9.3PEBaker, Armen, et al., 1983Vertical value; LBLHLM
9.3PEKajitani, Sugimori, et al., 1979Vertical value; LLK

Ion clustering data

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, 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:
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C3H10N+ + 12-Crown-4 = (C3H10N+ bullet 12-Crown-4)

By formula: C3H10N+ + C8H16O4 = (C3H10N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar150.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar174.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C4H5N2+ + 12-Crown-4 = (C4H5N2+ bullet 12-Crown-4)

By formula: C4H5N2+ + C8H16O4 = (C4H5N2+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar155.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar171.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C5H6N+ + 12-Crown-4 = (C5H6N+ bullet 12-Crown-4)

By formula: C5H6N+ + C8H16O4 = (C5H6N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar151.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar167.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C6H14N+ + 12-Crown-4 = (C6H14N+ bullet 12-Crown-4)

By formula: C6H14N+ + C8H16O4 = (C6H14N+ bullet C8H16O4)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar156.kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar146.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

Cesium ion (1+) + 12-Crown-4 = (Cesium ion (1+) bullet 12-Crown-4)

By formula: Cs+ + C8H16O4 = (Cs+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar84.9 ± 9.2kJ/molCIDTRodgers and Armentrout, 2000RCD

Potassium ion (1+) + 12-Crown-4 = (Potassium ion (1+) bullet 12-Crown-4)

By formula: K+ + C8H16O4 = (K+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar189. ± 12.kJ/molCIDTRodgers and Armentrout, 2000RCD

Lithium ion (1+) + 12-Crown-4 = (Lithium ion (1+) bullet 12-Crown-4)

By formula: Li+ + C8H16O4 = (Li+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar252. ± 13.kJ/molCIDTRodgers and Armentrout, 2000RCD

Sodium ion (1+) + 12-Crown-4 = (Sodium ion (1+) bullet 12-Crown-4)

By formula: Na+ + C8H16O4 = (Na+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar372. ± 51.kJ/molCIDTMore, Ray, et al., 1997RCD

Rubidium ion (1+) + 12-Crown-4 = (Rubidium ion (1+) bullet 12-Crown-4)

By formula: Rb+ + C8H16O4 = (Rb+ bullet C8H16O4)

Quantity Value Units Method Reference Comment
Deltar93. ± 13.kJ/molCIDTRodgers and Armentrout, 2000RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR 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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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, Ion clustering 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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Mass spectrum
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1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References