1,4-Butanediol

Formula: C₄H₁₀O₂
Molecular weight: 90.1210
IUPAC Standard InChI: InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
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
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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 ion energetics data

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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^- + = 1,4-Butanediol

By formula: C₄H₉O₂^- + H⁺ = C₄H₁₀O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1490. ± 10.	kJ/mol	G+TS	Crowder and Bartmess, 1993	gas phase; ΔGacid at 80°C; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1484. ± 8.4	kJ/mol	IMRE	Crowder and Bartmess, 1993	gas phase; ΔGacid at 80°C; B
Δ_rG°	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

Gas Chromatography

Go To: Top, Gas phase ion energetics data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Apiezon L	160.	900.	Bogoslovsky, Anvaer, et al., 1978	Celite 545
Packed	SE-30	175.	931.	Casteignau and Villessot, 1968	Column length: 3. m

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	PEG-2000	179.	1890.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	180.	1911.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	200.	1870.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	200.	1911.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	912.4	Sun and Stremple, 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 40. C; T_end: 325. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-1	922.	Peng, 2000	15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min)

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1861.	Shibamoto, 1987	Program: not specified

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

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]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Casteignau and Villessot, 1968
Casteignau, G.; Villessot, D., Identification par chromatographie en phase gaseuse de composés difonctionnels insaturés. I. Synthèse et indices de rétention, Bull. Soc. Chim. Fr., 1968, 9, 3893-3903. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Peng, 2000
Peng, C.T., Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index, J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8 . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

Notes

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Symbols used in this document:

AE Appearance energy

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions