1,4,7,10,13,16-Hexaoxacyclooctadecane

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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
Δcliquid-1687.8 ± 1.8kcal/molCcbMoses and Larson, 1980Corresponding Δfliquid = -260.59 kcal/mol (simple calculation by NIST; no Washburn corrections)
Quantity Value Units Method Reference Comment
Δfsolid-258.39 ± 0.67kcal/molCcbVasil'ev, Borodin, et al., 1992Authors Hf298_condensed=-1037.0±2.8 kJ/mol
Quantity Value Units Method Reference Comment
Δcsolid-1690.0 ± 1.2kcal/molCcbVasil'ev, Borodin, et al., 1992Authors Hf298_condensed=-1037.0±2.8 kJ/mol; Corresponding Δfsolid = -258.39 kcal/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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tfus310.KN/ADale and Kristiansen, 1972Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap20.6 ± 1.6kcal/molCGCNichols, Orf, et al., 2000AC
Quantity Value Units Method Reference Comment
Δsub28.5 ± 1.6kcal/molCGC-DSCNichols, Orf, et al., 2000AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
391. to 392.0.00007PCR Inc., 1990BS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
8.13312.2Dale, Kristiansen, et al., 1972AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

C4H5N2+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C4H5N2+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C4H5N2+ + C12H24O6 = (C4H5N2+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr44.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.600.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C5H6N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C5H6N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C5H6N+ + C12H24O6 = (C5H6N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr44.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.550.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C6H14N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C6H14N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C6H14N+ + C12H24O6 = (C6H14N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr48. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr38.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
23.670.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C3H10N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C3H10N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C3H10N+ + C12H24O6 = (C3H10N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr41.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr40.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
18.569.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Sodium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Sodium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Na+ + C12H24O6 = (Na+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr70.7 ± 4.5kcal/molCIDTRodgers and Armentrout, 2000RCD
Δr71.7 ± 4.5kcal/molCIDTMore, Ray, et al., 1999RCD

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
0.00.CIDTRodgers and Armentrout, 2000RCD
0.0298.CIDTMore, Ray, et al., 1999RCD

Cesium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Cesium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Cs+ + C12H24O6 = (Cs+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr40.2 ± 2.2kcal/molCIDTRodgers and Armentrout, 2000RCD

Rubidium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Rubidium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Rb+ + C12H24O6 = (Rb+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr45.7 ± 3.1kcal/molCIDTRodgers and Armentrout, 2000RCD

Potassium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Potassium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: K+ + C12H24O6 = (K+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr56.2 ± 3.1kcal/molCIDTRodgers and Armentrout, 2000RCD

Gas phase ion energetics data

Go To: Top, 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)231.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity217.4kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.9PEBaker, Armen, et al., 1983LBLHLM
9.7PEBaker, Armen, et al., 1983Vertical value; LBLHLM
9.70PEKajitani, Sugimori, et al., 1979Vertical value; LLK

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

Clustering reactions

C3H10N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C3H10N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C3H10N+ + C12H24O6 = (C3H10N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr41.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr40.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
18.569.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C4H5N2+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C4H5N2+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C4H5N2+ + C12H24O6 = (C4H5N2+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr44.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.600.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C5H6N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C5H6N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C5H6N+ + C12H24O6 = (C5H6N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr44.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.550.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

C6H14N+ + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (C6H14N+ • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: C6H14N+ + C12H24O6 = (C6H14N+ • C12H24O6)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr48. ± 4.kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr38.cal/mol*KN/AMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
23.670.PHPMSMeot-Ner (Mautner), 1983gas phase; Entropy change calculated or estimated; M

Cesium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Cesium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Cs+ + C12H24O6 = (Cs+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr40.2 ± 2.2kcal/molCIDTRodgers and Armentrout, 2000RCD

Potassium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Potassium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: K+ + C12H24O6 = (K+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr56.2 ± 3.1kcal/molCIDTRodgers and Armentrout, 2000RCD

Sodium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Sodium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Na+ + C12H24O6 = (Na+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr70.7 ± 4.5kcal/molCIDTRodgers and Armentrout, 2000RCD
Δr71.7 ± 4.5kcal/molCIDTMore, Ray, et al., 1999RCD

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
0.00.CIDTRodgers and Armentrout, 2000RCD
0.0298.CIDTMore, Ray, et al., 1999RCD

Rubidium ion (1+) + 1,4,7,10,13,16-Hexaoxacyclooctadecane = (Rubidium ion (1+) • 1,4,7,10,13,16-Hexaoxacyclooctadecane)

By formula: Rb+ + C12H24O6 = (Rb+ • C12H24O6)

Quantity Value Units Method Reference Comment
Δr45.7 ± 3.1kcal/molCIDTRodgers and Armentrout, 2000RCD

IR Spectrum

Go To: Top, 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, 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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Additional Data

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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 118818

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, 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.

Moses and Larson, 1980
Moses, D.J.; Larson, J.W., Electrostatic ring strain in crown ethers, Abstract of papers, 179th ACS National Meeting, Houston, TX, 1980, 984. [all data]

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]

Dale and Kristiansen, 1972
Dale, J.; Kristiansen, P.O., Macrocyclic Oligo-ethers Related to Ethylene Oxide., Acta Chem. Scand., 1972, 26, 1471, https://doi.org/10.3891/acta.chem.scand.26-1471 . [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]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Dale, Kristiansen, et al., 1972
Dale, Johannes; Kristiansen, Per Olav; Henriksen, Lars; Liaaen-Jensen, S.; Svensson, Sigfrid, Macrocyclic Oligo-ethers Related to Ethylene Oxide., Acta Chem. Scand., 1972, 26, 1471-1478, https://doi.org/10.3891/acta.chem.scand.26-1471 . [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]

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]

More, Ray, et al., 1999
More, M.B.; Ray, D.; Armentrout, P.B., Intrinsic Affinities of Alkali Cations for 15-Crown-5 and 18-Crown-6: Bond Dissociation Energies of Gas-Phase M+-Crown Ether Complexes, J. Am. Chem. Soc., 1999, 121, 2, 417, https://doi.org/10.1021/ja9823159 . [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, 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