2-Propen-1-ol
- Formula: C3H6O
- Molecular weight: 58.0791
- IUPAC Standard InChI: InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2
- IUPAC Standard InChIKey: XXROGKLTLUQVRX-UHFFFAOYSA-N
- CAS Registry Number: 107-18-6
- 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: Allyl alcohol; Allylic alcohol; Shell Unkrauttod A; Vinylcarbinol; 1-Propen-3-ol; 2-Propenol; 2-Propenyl alcohol; 3-Hydroxypropene; CH2=CHCH2OH; Propen-1-ol-3; Alcool allylique; Allilowy alkohol; Allyl al; Allylalkohol; Propenyl alcohol; Weed drench; 1-Propenol-3; AA; Alcool allilco; 2-Propene-1-ol; Rcra waste number P005; Shell unkrautted A; UN 1098; 3-Hydroxy-1-propene; 1-Propenol-3-ol; Propenol-3; 1-Hydroxy-2-propene; prop-2-en-1-ol; NSC 6526; 2-propen-1-ol (allyl alcohol)
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -123.6 ± 1.5 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 76.02 | 298.15 | Stull D.R., 1969 | Please also see Kobe K.A., 1951.; GT |
| 76.36 | 300. | ||
| 95.44 | 400. | ||
| 112.09 | 500. | ||
| 125.98 | 600. | ||
| 137.70 | 700. | ||
| 147.61 | 800. | ||
| 156.27 | 900. | ||
| 163.43 | 1000. |
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: Eugene S. Domalski and Elizabeth D. Hearing
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 138.9 | 298. | von Reis, 1881 | T = 291 to 369 K. |
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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C3H5O- + =
By formula: C3H5O- + H+ = C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1563. ± 12. | kJ/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
| ΔrH° | 1400. ± 50. | kJ/mol | Acid | Kuhn, Fenzlaff, et al., 1988 | gas phase; From CH2=CHCH2OH, AP 0.9 eV; est. thermo = 2.5 eV; B |
| ΔrH° | 1409. ± 8.4 | kJ/mol | D-EA | Bouby, Compton, et al., 1968 | gas phase; EA probably 2 eV less; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1534. ± 12. | kJ/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
| ΔrG° | 1380. ± 8.8 | kJ/mol | H-TS | Bouby, Compton, et al., 1968 | gas phase; EA probably 2 eV less; B |
+
=
By formula: C3H6O + H2 = C3H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -130.6 ± 1.8 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -132. ± 1. kJ/mol; At 355°K; ALS |
+
=
+
By formula: C3H5I + H2O = HI + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -8.79 | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: C3H5Br + H2O = HBr + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -15. | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
=
By formula: C3H6O = C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -32. | kJ/mol | Eqk | Polkovnikova and Lapiclus, 1974 | gas phase; At 300 K; ALS |
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:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C3H6O+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.67 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.70 | EI | Holmes, Burgers, et al., 1982 | LBLHLM |
| 9.63 | PE | Katrib and Rabalais, 1973 | LLK |
| 9.67 ± 0.05 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
| 10.22 | PE | Mines and Thompson, 1973 | Vertical value; LLK |
De-protonation reactions
C3H5O- + =
By formula: C3H5O- + H+ = C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1563. ± 12. | kJ/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
| ΔrH° | 1400. ± 50. | kJ/mol | Acid | Kuhn, Fenzlaff, et al., 1988 | gas phase; From CH2=CHCH2OH, AP 0.9 eV; est. thermo = 2.5 eV; B |
| ΔrH° | 1409. ± 8.4 | kJ/mol | D-EA | Bouby, Compton, et al., 1968 | gas phase; EA probably 2 eV less; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1534. ± 12. | kJ/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
| ΔrG° | 1380. ± 8.8 | kJ/mol | H-TS | Bouby, Compton, et al., 1968 | gas phase; EA probably 2 eV less; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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.
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Kobe K.A., 1951
Kobe K.A.,
Thermochemistry for the petrochemical industry. Part XVII. Some C3 oxygenated hydrocarbons,
Petrol. Refiner, 1951, 30 (8), 119-122. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Graul, Schnute, et al., 1990
Graul, S.T.; Schnute, M.E.; Squires, R.R.,
Gas-Phase Acidities of Carboxylic Acids and Alcohols from Collision-Induced Dissociation of Dimer Cluster Ions,
Int. J. Mass Spectrom. Ion Proc., 1990, 96, 2, 181, https://doi.org/10.1016/0168-1176(90)87028-F
. [all data]
Kuhn, Fenzlaff, et al., 1988
Kuhn, A.; Fenzlaff, H.-P.; Illenberger, E.,
Formation and Dissociation of Negative Ion Resonances in Methanol and Allyl Alcohol,
J. Chem. Phys., 1988, 88, 12, 7453, https://doi.org/10.1063/1.454309
. [all data]
Bouby, Compton, et al., 1968
Bouby, L.; Compton, R.N.; Souleyrol, A.,
Formation d'ions negatifs dans l'alcool allylique et l'acroleine.,
Comptes Rendues. Acad. Sc. Paris, 1968, 266, 1250. [all data]
Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A.,
Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X,
J. Chem. Soc., 1949, 1145-1148. [all data]
Polkovnikova and Lapiclus, 1974
Polkovnikova, A.G.; Lapiclus, V.L.,
Calculation of the equilibrium and heat of isomerization of propylene oxide on a lithium phosphate catalyst,
Neftekhimiya, 1974, 14, 113-115. [all data]
Holmes, Burgers, et al., 1982
Holmes, J.L.; Burgers, P.C.; Mollah, Y.A.,
Alkane elimination from ionized alkanols,
Org. Mass Spectrom., 1982, 17, 127. [all data]
Katrib and Rabalais, 1973
Katrib, A.; Rabalais, J.W.,
Electronic interaction between the vinyl group and its substituents,
J. Phys. Chem., 1973, 77, 2358. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Mines and Thompson, 1973
Mines, G.W.; Thompson, H.W.,
Photoelectron spectra of vinyl and allyl halides,
Spectrochim. Acta Part A, 1973, 29, 1377. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions 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
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