15-Crown-5
- Formula: C10H20O5
- Molecular weight: 220.2628
- 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
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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°gas | -799.5 ± 2.0 | kJ/mol | Ccr | Bystrm and Mansson, 1982 |
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° | 146. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 149. | J/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° | 172. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 178. | J/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° | 177. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 153. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: Na+ + C10H20O5 = (Na+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 294. ± 18. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
ΔrH° | 298. ± 18. | kJ/mol | CIDT | More, Ray, et al., 1999 | RCD |
By formula: Cs+ + C10H20O5 = (Cs+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. ± 5.9 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: Rb+ + C10H20O5 = (Rb+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 114. ± 7.1 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: K+ + C10H20O5 = (K+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 205. ± 15. | kJ/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) | 943.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 899.7 | kJ/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 |
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
By formula: C3H10N+ + C10H20O5 = (C3H10N+ • C10H20O5)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 146. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 149. | J/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° | 172. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 178. | J/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° | 177. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 153. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1983 | gas phase; M |
By formula: Cs+ + C10H20O5 = (Cs+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. ± 5.9 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: K+ + C10H20O5 = (K+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 205. ± 15. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
By formula: Na+ + C10H20O5 = (Na+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 294. ± 18. | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
ΔrH° | 298. ± 18. | kJ/mol | CIDT | More, Ray, et al., 1999 | RCD |
By formula: Rb+ + C10H20O5 = (Rb+ • C10H20O5)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 114. ± 7.1 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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
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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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]
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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References
- 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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