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
- IUPAC Standard InChIKey: VFTFKUDGYRBSAL-UHFFFAOYSA-N
- 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
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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, Gas Chromatography, 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 | -191.1 ± 0.48 | kcal/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 | -210.1 ± 0.47 | kcal/mol | Ccr | Bystrm and Mansson, 1982 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1413.6 ± 0.34 | kcal/mol | Ccr | Bystrm and Mansson, 1982 | Corresponding ΔfHºliquid = -210.1 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -1410.9 ± 1.8 | kcal/mol | Ccb | Moses and Larson, 1980 | See Moses and Larson, 1979; Corresponding ΔfHºliquid = -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 |
|---|---|---|---|---|---|
| ΔvapH° | 19.02 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 18.1 ± 0.41 | kcal/mol | CGC | Nichols, Orf, et al., 2000 | AC |
| ΔvapH° | 19.02 ± 0.069 | kcal/mol | C | Bystrm and Mansson, 1982 | ALS |
| ΔvapH° | 19.0 | kcal/mol | N/A | Bystrm and Mansson, 1982 | DRB |
| ΔvapH° | 19.0 ± 0.07 | kcal/mol | C | Bystr«65533»m and M«65533»nsson, 1982 | AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 390.7 | 0.0003 | Aldrich Chemical Company Inc., 1990 | BS |
| 351. | 0.00007 | PCR Inc., 1990 | BS |
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+ + C10H20O5 = (C3H10N+ • C10H20O5)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 34.9 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 35.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: C5H6N+ + C10H20O5 = (C5H6N+ • C10H20O5)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 41.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 42.6 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: C6H14N+ + C10H20O5 = (C6H14N+ • C10H20O5)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 42.3 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 36.5 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
+
= (
•
)
By formula: Na+ + C10H20O5 = (Na+ • C10H20O5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 70.3 ± 4.3 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
| ΔrH° | 71.2 ± 4.3 | kcal/mol | CIDT | More, Ray, et al., 1999 | RCD |
+
= (
•
)
By formula: Cs+ + C10H20O5 = (Cs+ • C10H20O5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.9 ± 1.4 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
+
= (
•
)
By formula: Rb+ + C10H20O5 = (Rb+ • C10H20O5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 27.2 ± 1.7 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
+
= (
•
)
By formula: K+ + C10H20O5 = (K+ • C10H20O5)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 49.0 ± 3.6 | kcal/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
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) | 225.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 215.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.9 | PE | Kajitani, Sugimori, et al., 1979 | LLK |
| 9.6 | PE | Baker, Armen, et al., 1983 | Vertical value; LBLHLM |
| 9.58 | PE | Kajitani, Sugimori, et al., 1979 | Vertical 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
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 1554. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2431. | Njoroge, Koaze, et al., 2005 | 60. 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
- Symbols used in this document:
Tboil Boiling point 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 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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