Cyclopropanecarboxaldehyde
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChI: InChI=1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2
- IUPAC Standard InChIKey: JMYVMOUINOAAPA-UHFFFAOYSA-N
- CAS Registry Number: 1489-69-6
- 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: Cyclopropylcarboxaldehyde
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Gas phase ion energetics data
Go To: Top, 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: John E. Bartmess
View reactions leading to C4H6O+ (ion structure unspecified)
De-protonation reactions
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1631. ± 21. | kJ/mol | G+TS | Baschky, Peterson, et al., 1994 | gas phase; Between D2O and PhF. Cis and Trans anions do not interconvert and have same expt. acidity. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1598. ± 21. | kJ/mol | IMRB | Baschky, Peterson, et al., 1994 | gas phase; Between D2O and PhF. Cis and Trans anions do not interconvert and have same expt. acidity. |
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1572. ± 8.8 | kJ/mol | G+TS | Chou, Dahlke, et al., 1993 | gas phase; barrier for opening to CH2=C(CHO)CH2-: 29 kcal/mol. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1543. ± 8.4 | kJ/mol | IMRE | Chou, Dahlke, et al., 1993 | gas phase; barrier for opening to CH2=C(CHO)CH2-: 29 kcal/mol. |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Baschky, Peterson, et al., 1994
Baschky, M.C.; Peterson, K.C.; Kass, S.R.,
Stereospecificity in the gas phase. Formation and characterization of configurationally stable cyclopropyl anions,
J. Am. Chem. Soc., 1994, 116, 16, 7218, https://doi.org/10.1021/ja00095a026
. [all data]
Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R.,
Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions,
J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy 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.