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
View 3d structure (requires JavaScript / HTML 5) - 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:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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 | -799.5 ± 2.0 | kJ/mol | Ccr | Bystrm and Mansson, 1982 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry 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 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 Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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]
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 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.