15-Crown-5

• Formula: C₁₀H₂₀O₅
• Molecular weight: 220.2628
• IUPAC Standard InChI: InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 Copy

  
• IUPAC Standard InChIKey: VFTFKUDGYRBSAL-UHFFFAOYSA-N Copy
• CAS Registry Number: 33100-27-5
• 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: 1,4,7,10,13-Pentaoxacyclopentadecane; 15-Crown-5 ether; 1,4,10,13-pentaoxacyclopentadecane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
• Options:
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Gas 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

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₀H₂₀O₅ = (C₃H₁₀N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₁₀H₂₀O₅ = (C₅H₆N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₀H₂₀O₅ = (C₆H₁₄N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  = ( • )

By formula: Na⁺ + C₁₀H₂₀O₅ = (Na⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: Cs⁺ + C₁₀H₂₀O₅ = (Cs⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: Rb⁺ + C₁₀H₂₀O₅ = (Rb⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: K⁺ + C₁₀H₂₀O₅ = (K⁺ • C₁₀H₂₀O₅)

Gas phase ion energetics 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 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

Ionization energy determinations

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⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₀H₂₀O₅ = (C₃H₁₀N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₁₀H₂₀O₅ = (C₅H₆N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₀H₂₀O₅ = (C₆H₁₄N⁺ • C₁₀H₂₀O₅)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  = ( • )

By formula: Cs⁺ + C₁₀H₂₀O₅ = (Cs⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: K⁺ + C₁₀H₂₀O₅ = (K⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: Na⁺ + C₁₀H₂₀O₅ = (Na⁺ • C₁₀H₂₀O₅)

 +  = ( • )

By formula: Rb⁺ + C₁₀H₂₀O₅ = (Rb⁺ • C₁₀H₂₀O₅)

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, polar column, temperature ramp

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, 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]

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]

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]

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]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Njoroge, Koaze, et al., 2005
Njoroge, S.M.; Koaze, H.; Karanja, P.N.; Sawamura, M., Essential oil constituents of three varieties of Kenyan sweet oranges (Citrus sinensis), Flavour Fragr. J., 2005, 20, 1, 80-85, https://doi.org/10.1002/ffj.1377 . [all data]

Notes

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• Symbols used in this document:
  

  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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