15-Crown-5

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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

Quantity Value Units Method Reference Comment
Δfgas-191.1 ± 0.48kcal/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
Δfliquid-210.1 ± 0.47kcal/molCcrBystrm and Mansson, 1982 
Quantity Value Units Method Reference Comment
Δcliquid-1413.6 ± 0.34kcal/molCcrBystrm and Mansson, 1982Corresponding Δfliquid = -210.1 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-1410.9 ± 1.8kcal/molCcbMoses and Larson, 1980See Moses and Larson, 1979; Corresponding Δfliquid = -212.81 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
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
Δvap19.02kcal/molN/AMajer and Svoboda, 1985 
Δvap18.1 ± 0.41kcal/molCGCNichols, Orf, et al., 2000AC
Δvap19.02 ± 0.069kcal/molCBystrm and Mansson, 1982ALS
Δvap19.0kcal/molN/ABystrm and Mansson, 1982DRB
Δvap19.0 ± 0.07kcal/molCBystr«65533»m and M«65533»nsson, 1982AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
390.70.0003Aldrich Chemical Company Inc., 1990BS
351.0.00007PCR Inc., 1990BS

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+ + 15-Crown-5 = (C3H10N+ • 15-Crown-5)

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr34.9kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Δr35.6cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C5H6N+ + 15-Crown-5 = (C5H6N+ • 15-Crown-5)

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr41.0kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Δr42.6cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

C6H14N+ + 15-Crown-5 = (C6H14N+ • 15-Crown-5)

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Δr42.3kcal/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Δr36.5cal/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

Sodium ion (1+) + 15-Crown-5 = (Sodium ion (1+) • 15-Crown-5)

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

Quantity Value Units Method Reference Comment
Δr70.3 ± 4.3kcal/molCIDTRodgers and Armentrout, 2000RCD
Δr71.2 ± 4.3kcal/molCIDTMore, Ray, et al., 1999RCD

Cesium ion (1+) + 15-Crown-5 = (Cesium ion (1+) • 15-Crown-5)

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

Quantity Value Units Method Reference Comment
Δr23.9 ± 1.4kcal/molCIDTRodgers and Armentrout, 2000RCD

Rubidium ion (1+) + 15-Crown-5 = (Rubidium ion (1+) • 15-Crown-5)

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

Quantity Value Units Method Reference Comment
Δr27.2 ± 1.7kcal/molCIDTRodgers and Armentrout, 2000RCD

Potassium ion (1+) + 15-Crown-5 = (Potassium ion (1+) • 15-Crown-5)

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

Quantity Value Units Method Reference Comment
Δr49.0 ± 3.6kcal/molCIDTRodgers and Armentrout, 2000RCD

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

Quantity Value Units Method Reference Comment
Proton affinity (review)225.6kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity215.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.9PEKajitani, Sugimori, et al., 1979LLK
9.6PEBaker, Armen, et al., 1983Vertical value; LBLHLM
9.58PEKajitani, Sugimori, et al., 1979Vertical value; LLK

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

View large format table.

Column type Active phase I Reference Comment
CapillaryUltra-11554.Okumura, 199125. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax2431.Njoroge, Koaze, et al., 200560. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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]

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]

Moses and Larson, 1979
Moses, D.J.; Larson, J.W., The enthalpies of combustion of two crown ethers, Personal Communication, 1979, 1-21. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References