1,4-Butanediol
- Formula: C4H10O2
- Molecular weight: 90.1210
- IUPAC Standard InChIKey: WERYXYBDKMZEQL-UHFFFAOYSA-N
- CAS Registry Number: 110-63-4
- 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: Diol 14B; Sucol B; Tetramethylene glycol; 1,4-Butylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; Butane-1,4-diol; Butanediol; 1,4-BD; Tetramethylene 1,4-diol; BDO; Butylene glycol; Dabco BDO; Butane diol-1,4; NSC 406696
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -426.0 ± 5.7 | kJ/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989 |
ΔfH°gas | -427. ± 3. | kJ/mol | Ccb | Gardner and Hussain, 1972 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -505.3 ± 5.7 | kJ/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989; ALS |
ΔfH°liquid | -503. ± 2. | kJ/mol | Ccb | Gardner and Hussain, 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2495.5 ± 5.7 | kJ/mol | Ccr | Knauth and Sabbah, 1990 | see Knauth and Sabbah, 1989; Corresponding ΔfHºliquid = -507.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -2499.9 ± 2.0 | kJ/mol | Ccb | Gardner and Hussain, 1972 | Corresponding ΔfHºliquid = -503.25 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 223.4 | J/mol*K | N/A | Nistratov, Babinkov, et al., 1979 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
200.1 | 298.15 | Nistratov, Babinkov, et al., 1979 | T = 5 to 320 K.; DH |
178. | 297.79 | Petit and TerMinassian, 1974 | T = 297 to 470 K. Value is unsmoothed experimental datum.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 915.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 854.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
>875.0 | Bouchoux, Buisson, et al., 2003 | MM |
>871.7 | Bouchoux, Buisson, et al., 2003 | MM |
>884.3 ± 0.5 | Bouchoux, Buisson, et al., 2003 | MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
843.5 | Bouchoux, Buisson, et al., 2003 | MM |
841.2 | Bouchoux, Buisson, et al., 2003 | MM |
852.9 ± 0.5 | Bouchoux, Buisson, et al., 2003 | MM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H6+ | 11.1 ± 0.1 | H2O+CH2O | EI | Holmes, Mommers, et al., 1984 | LBLHLM |
C3H8O+ | 10.70 ± 0.05 | CH2O | EI | Holmes, Mommers, et al., 1984 | LBLHLM |
De-protonation reactions
C4H9O2- + =
By formula: C4H9O2- + H+ = C4H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1490. ± 10. | kJ/mol | G+TS | Crowder and Bartmess, 1993 | gas phase; ΔGacid at 80°C; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1484. ± 8.4 | kJ/mol | IMRE | Crowder and Bartmess, 1993 | gas phase; ΔGacid at 80°C; B |
ΔrG° | 1507.1 ± 1.3 | kJ/mol | CIDC | Houriet, Tabet, et al., 1984 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Knauth and Sabbah, 1990
Knauth, P.; Sabbah, R.,
Energetics of intra- and intermolecular bonds in ω-alkanediols (II) Thermochemical study of 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, and 1,5-pentanediol at 298.15K,
Struct. Chem., 1990, 1, 43-46. [all data]
Knauth and Sabbah, 1989
Knauth, P.; Sabbah, R.,
Combustion calorimetry on milligram samples of liquid substances with a CRMT rocking bomb calorimeter. Application to the study of ω-alkanediol at 298.15 K,
J. Chem. Thermodyn., 1989, 21, 203-210. [all data]
Gardner and Hussain, 1972
Gardner, P.J.; Hussain, K.S.,
The standard enthalpies of formation of some aliphatic diols,
J. Chem. Thermodyn., 1972, 4, 819-827. [all data]
Nistratov, Babinkov, et al., 1979
Nistratov, V.P.; Babinkov, A.G.; Shvetsova, K.G.; Lapteva, S.A.,
Heat capacity and termodynamic functions of tetramethyleneglycol,
Termodin. Org. Soedin., 1979, (8), 33-36. [all data]
Petit and TerMinassian, 1974
Petit, J.C.; TerMinassian, L.,
Measurements of (dV/dT)p, (dV/dP)T, and (dH/dT)p by flux calorimetry,
J. Chem. Thermodynam., 1974, 6, 1139-1152. [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]
Bouchoux, Buisson, et al., 2003
Bouchoux, G.; Buisson, D.A.; Bourcier, S.; Sablier, M.,
Application of the kinetic method to bifunctional bases. ESI tandem quadrupole experiments,
Int. J. Mass Spectrom., 2003, 228, 1035. [all data]
Holmes, Mommers, et al., 1984
Holmes, J.L.; Mommers, A.A.; Szulejko, J.E.; Terlouw, J.K.,
Two new stable [C3H8O]+ isomers: The radical cations [C3H6OH2]+,
J. Chem. Soc., Chem. Commun., 1984, 165. [all data]
Crowder and Bartmess, 1993
Crowder, C.; Bartmess, J.,
The Gas Phase Acidities of Diols,
J. Am. Soc. Mass Spectrom., 1993, 4, 9, 723, https://doi.org/10.1016/1044-0305(93)80051-Y
. [all data]
Houriet, Tabet, et al., 1984
Houriet, R.; Tabet, J.-C.; Tchapla, A.,
Gas-phase Acidities of Aliphatic and Cyclic Diols,
Spectros. Int. J., (1984),, 1984, 3, 132.. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions 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 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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