Ethanol

Formula: C₂H₆O
Molecular weight: 46.0684
IUPAC Standard InChI: InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
IUPAC Standard InChIKey: LFQSCWFLJHTTHZ-UHFFFAOYSA-N
CAS Registry Number: 64-17-5
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.
Isotopologues:
Other names: Ethyl alcohol; Alcohol; Alcohol anhydrous; Algrain; Anhydrol; Denatured ethanol; Ethyl hydrate; Ethyl hydroxide; Jaysol; Jaysol S; Methylcarbinol; SD Alchol 23-hydrogen; Tecsol; C2H5OH; Absolute ethanol; Cologne spirit; Fermentation alcohol; Grain alcohol; Molasses alcohol; Potato alcohol; Aethanol; Aethylalkohol; Alcohol, dehydrated; Alcool ethylique; Alcool etilico; Alkohol; Cologne spirits; Denatured alcohol CD-10; Denatured alcohol CD-5; Denatured alcohol CD-5a; Denatured alcohol SD-1; Denatured alcohol SD-13a; Denatured alcohol SD-17; Denatured alcohol SD-23a; Denatured alcohol SD-28; Denatured alcohol SD-3a; Denatured alcohol SD-30; Denatured alcohol SD-39b; Denatured alcohol SD-39c; Denatured alcohol SD-40m; Etanolo; Ethanol 200 proof; Ethyl alc; Etylowy alkohol; EtOH; NCI-C03134; Spirits of wine; Spirt; Alkoholu etylowego; Ethyl alcohol anhydrous; SD alcohol 23-hydrogen; UN 1170; Tecsol C; Alcare Hand Degermer; Absolute alcohol; Denatured alcohol; Ethanol, silent spirit; Ethylol; Punctilious ethyl alcohol; SD 3A
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Information on this page:
Other data available:
- Gas phase thermochemistry data
- Condensed phase thermochemistry data
- Reaction thermochemistry data: reactions 1 to 50, reactions 51 to 77
- Henry's Law data
- IR Spectrum
- Mass spectrum (electron ionization)
- Gas Chromatography
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Phase change data

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

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity	Value	Units	Method	Reference	Comment
T_boil	351.5 ± 0.2	K	AVG	N/A	Average of 138 out of 148 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	159. ± 2.	K	AVG	N/A	Average of 11 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	150. ± 20.	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_c	514. ± 7.	K	AVG	N/A	Average of 37 out of 38 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
P_c	63. ± 4.	bar	AVG	N/A	Average of 18 out of 19 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
V_c	0.168	l/mol	N/A	Gude and Teja, 1995
Quantity	Value	Units	Method	Reference	Comment
ρ_c	6.0 ± 0.2	mol/l	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	42.3 ± 0.4	kJ/mol	AVG	N/A	Average of 12 out of 13 values; Individual data points

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
38.56	351.5	N/A	Majer and Svoboda, 1985
41.7	326.	N/A	Mejia, Segura, et al., 2010	Based on data from 311. to 351. K.; AC
39.3	338.	N/A	Aucejo, Loras, et al., 1999	Based on data from 323. to 357. K.; AC
40.7	321.	EB	Diogo, Santos, et al., 1995	Based on data from 309. to 343. K.; AC
40.5	357.	N/A	Ortega, Susial, et al., 1990	Based on data from 342. to 357. K.; AC
35.2	393.	C	Vine and Wormald, 1989	AC
30.6	423.	C	Vine and Wormald, 1989	AC
25.7	453.	C	Vine and Wormald, 1989	AC
21.8	473.	C	Vine and Wormald, 1989	AC
17.3	493.	C	Vine and Wormald, 1989	AC
14.2	503.	C	Vine and Wormald, 1989	AC
40.9	320.	C	Dong, Lin, et al., 1988	AC
40.4	328.	C	Dong, Lin, et al., 1988	AC
40.2	335.	C	Dong, Lin, et al., 1988	AC
39.4	344.	C	Dong, Lin, et al., 1988	AC
38.8	351.	C	Dong, Lin, et al., 1988	AC
41.3	335.	A	Stephenson and Malanowski, 1987	Based on data from 320. to 359. K.; AC
45.6	256.	A	Stephenson and Malanowski, 1987	Based on data from 210. to 271. K.; AC
44.	208.	A	Stephenson and Malanowski, 1987	Based on data from 193. to 223. K.; AC
41.3	335.	A	Stephenson and Malanowski, 1987	Based on data from 320. to 359. K.; AC
40.1	361.	A	Stephenson and Malanowski, 1987	Based on data from 349. to 374. K.; AC
39.1	385.	A	Stephenson and Malanowski, 1987	Based on data from 370. to 464. K.; AC
36.1	474.	A	Stephenson and Malanowski, 1987	Based on data from 459. to 514. K.; AC
42.5	307.	A	Stephenson and Malanowski, 1987	Based on data from 292. to 353. K.; AC
42.5	308.	A,EB	Stephenson and Malanowski, 1987	Based on data from 293. to 366. K. See also Ambrose, Counsell, et al., 1970.; AC
42.9	286.	N/A	Wilhoit and Zwolinski, 1973	Based on data from 271. to 373. K.; AC
41.0 ± 0.1	320.	C	Counsell, Fenwick, et al., 1970	AC
40.0 ± 0.1	335.	C	Counsell, Fenwick, et al., 1970	AC
38.7 ± 0.1	351.	C	Counsell, Fenwick, et al., 1970	AC
42.4	303.	N/A	Van Ness, Soczek, et al., 1967	Based on data from 288. to 348. K.; AC
42.2	313.	N/A	Kretschmer and Wiebe, 1949	Based on data from 298. to 351. K.; AC
40.0	351.	N/A	Oguri, Anjo, et al., 1934	AC
54.1	301.	N/A	Kahlbaum, 1883	Based on data from 286. to 351. K.; AC

Enthalpy of vaporization

Δ_vapH = A exp(-αT_r) (1 − T_r)^β
Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
T_r = reduced temperature (T / T_c)

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Temperature (K)	298. to 469.
A (kJ/mol)	50.43
α	-0.4475
β	0.4989
T_c (K)	513.9
Reference	Majer and Svoboda, 1985

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
364.8 to 513.91	4.92531	1432.526	-61.819	Ambrose, Sprake, et al., 1975	Coefficents calculated by NIST from author's data.
292.77 to 366.63	5.24677	1598.673	-46.424	Ambrose and Sprake, 1970	Coefficents calculated by NIST from author's data.
273. to 351.70	5.37229	1670.409	-40.191	Kretschmer and Wiebe, 1949	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Reference	Comment
4.973	159.	Yoshida, 1944	DH
5.021	158.5	Kelley, 1929	DH
4.626	156.2	Gibson, Parks, et al., 1920	DH
4.64	158.8	Domalski and Hearing, 1996	AC
4.962	158.7	Parks, 1925	DH

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
31.3	159.	Yoshida, 1944	DH
31.68	158.5	Kelley, 1929	DH
21.22	158.7	Parks, 1925	DH

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
28.16	111.4	Domalski and Hearing, 1996	CAL
29.25	158.8
5.2	127.5
31.0	159.

Enthalpy of phase transition

ΔH_trs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.659	127.5	crystaline, II	liquid	Haida, Suga, et al., 1977	DH
4.931	159.00	crystaline, I	liquid	Haida, Suga, et al., 1977	DH
3.138	111.4	crystaline, II	crystaline, I	Nikolaev, Rabinovich, et al., 1967	DH
4.644	158.8	crystaline, I	liquid	Nikolaev, Rabinovich, et al., 1967	DH

Entropy of phase transition

ΔS_trs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
5.19	127.5	crystaline, II	liquid	Haida, Suga, et al., 1977	DH
31.01	159.00	crystaline, I	liquid	Haida, Suga, et al., 1977	DH
28.17	111.4	crystaline, II	crystaline, I	Nikolaev, Rabinovich, et al., 1967	DH
29.24	158.8	crystaline, I	liquid	Nikolaev, Rabinovich, et al., 1967	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas phase ion energetics data

Go To: Top, Phase change data, Ion clustering data, References, Notes

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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 C₂H₆O⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.48 ± 0.07	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	776.4	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	746.	kJ/mol	N/A	Hunter and Lias, 1998	HL

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
779.4 ± 0.8	Tabrizchi and Shooshtari, 2003	T = 403-453K; Authors report only relative PAs. Absolute values are referenced here to PA(CH3COOC2H5) = 835.7 kJ/mol as listed in Hunter and Lias, 1998, although average PA(CH3COOC2H5) from the literature sources in Hunter and Lias, 1998 is 831.0 kJ/mol; MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.41 ± 0.05	EI	Holmes and Lossing, 1991	LL
10.4	PE	Ohno, Imai, et al., 1985	LBLHLM
10.47 ± 0.07	EI	Bowen and Maccoll, 1984	LBLHLM
10.3	PE	Ohno, Imai, et al., 1983	LBLHLM
10.5	EI	Mishchanchuk, Pokrovskii, et al., 1982	LBLHLM
10.7	PE	Von Niessen, Bieri, et al., 1980	LLK
10.49 ± 0.01	PI	Potapov and Sorokin, 1972	LLK
10.46 ± 0.02	PE	Cocksey, Eland, et al., 1971	LLK
10.65	PE	Baker, Betteridge, et al., 1971	LLK
10.46	PE	Dewar and Worley, 1969	RDSH
10.47 ± 0.02	PI	Refaey and Chupka, 1968	RDSH
10.48 ± 0.05	PI	Watanabe, Nakayama, et al., 1962	RDSH
10.64	PE	Ohno, Imai, et al., 1985	Vertical value; LBLHLM
10.64	PE	Utsunomiya, Kobayashi, et al., 1980	Vertical value; LLK
10.65	PE	Hoppilliard and Solgadi, 1980	Vertical value; LLK
10.61	PE	Benoit and Harrison, 1977	Vertical value; LLK
10.65 ± 0.03	PE	Peel and Willett, 1975	Vertical value; LLK
10.59	PE	Vovna, Lopatin, et al., 1974	Vertical value; LLK
10.04	PE	Schweig and Thiel, 1974	Vertical value; LLK
10.62	PE	Robin and Kuebler, 1973	Vertical value; LLK
10.64	PE	Katsumata, Iwai, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C⁺	22.9 ± 0.5	H₂+H+CH₂OH	EI	Stepanov, Perov, et al., 1988	LL
CH₂O⁺	11.70	CH₄	PI	Refaey and Chupka, 1968	RDSH
CH₃⁺	14.70 ± 0.10	?	EI	Haney and Franklin, 1969	RDSH
CH₃O⁺	11.25 ± 0.09	CH₃	EI	Bowen and Maccoll, 1984	LBLHLM
CH₃O⁺	11.40 ± 0.06	CH₃	EI	Selim and Helal, 1981	LLK
CH₃O⁺	11.30	CH₃	EI	Lossing, 1977	LLK
CH₃O⁺	11.20 ± 0.05	CH₃	PI	Potapov and Sorokin, 1972	LLK
CH₃O⁺	11.25	CH₃	PI	Refaey and Chupka, 1968	RDSH
C₂H₃⁺	14.7	?	EI	Friedman, Long, et al., 1957	RDSH
C₂H₃O⁺	14.5	H₂+H	EI	Friedman, Long, et al., 1957	RDSH
C₂H₄⁺	12.0 ± 0.9	H₂O	EI	Bowen and Maccoll, 1984	LBLHLM
C₂H₄⁺	12.0	H₂O	PI	Refaey and Chupka, 1968	RDSH
C₂H₄O⁺	~10.45	H₂	EI	Holmes, Terlouw, et al., 1976	LLK
C₂H₅⁺	12.7	OH	PI	Refaey and Chupka, 1968	RDSH
C₂H₅O⁺	10.78 ± 0.09	H	EI	Bowen and Maccoll, 1984	LBLHLM
C₂H₅O⁺	10.6	H	EI	Mishchanchuk, Pokrovskii, et al., 1982	LBLHLM
C₂H₅O⁺	10.67	H	EI	Lossing, 1977	LLK
C₂H₅O⁺	10.75 ± 0.03	H	EI	Solka and Russell, 1974	LLK
C₂H₅O⁺	10.80 ± 0.05	H	PI	Potapov and Sorokin, 1972	LLK
C₂H₅O⁺	10.78 ± 0.02	H	PI	Refaey and Chupka, 1968	RDSH
C₂H₅O⁺[CH₃CHOH⁺]	10.801 ± 0.005	H	PI	Ruscic and Berkowitz, 1994	T = 0K; LL
H⁺	21.0 ± 0.5	CH₂+CH₂OH	EI	Stepanov, Perov, et al., 1988	LL
H₂O⁺	13.06	C₂H₄	EI	Lewis and Hamill, 1970	RDSH
H₃O⁺	13.8	H₂+C₂H₃	PIPECO	Niwa, Nishimura, et al., 1982	LBLHLM
H₃O⁺	14.30 ± 0.02	?	EI	Haney and Franklin, 1969, 2	RDSH
O⁺	21.7 ± 0.5	2CH₃	EI	Stepanov, Perov, et al., 1988	LL

De-protonation reactions

C₂H₅O^- + = Ethanol

By formula: C₂H₅O^- + H⁺ = C₂H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1587. ± 4.2	kJ/mol	D-EA	Ramond, Davico, et al., 2000	gas phase; B
Δ_rH°	1582. ± 8.4	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rH°	1579. ± 8.8	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1586.2 ± 0.42	kJ/mol	CIDT	DeTuri and Ervin, 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1559. ± 4.6	kJ/mol	H-TS	Ramond, Davico, et al., 2000	gas phase; B
Δ_rG°	1554. ± 8.8	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rG°	1551. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

Anion protonation reactions

C₂H₅O^- + = Ethanol

By formula: C₂H₅O^- + H⁺ = C₂H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1587. ± 4.2	kJ/mol	D-EA	Ramond, Davico, et al., 2000	gas phase; B
Δ_rH°	1582. ± 8.4	kJ/mol	CIDC	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rH°	1579. ± 8.8	kJ/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1586.2 ± 0.42	kJ/mol	CIDT	DeTuri and Ervin, 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1559. ± 4.6	kJ/mol	H-TS	Ramond, Davico, et al., 2000	gas phase; B
Δ_rG°	1554. ± 8.8	kJ/mol	H-TS	Haas and Harrison, 1993	gas phase; Both metastable and 50 eV collision energy.; B
Δ_rG°	1551. ± 8.4	kJ/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

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

Data compiled as indicated in comments:
B - John E. Bartmess
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

+ Ethanol = C₂H₆BrO^-

By formula: Br^- + C₂H₆O = C₂H₆BrO^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	58.99 ± 0.84	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	34.3	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	37. ± 8.4	kJ/mol	IMRE	Tanabe, Morgon, et al., 1996	gas phase; Anchored to H2O..Br- of Hiraoka, Mizure, et al., 19882; B

+ 2 Ethanol = C₄H₁₂BrO₂^-

By formula: Br^- + 2C₂H₆O = C₄H₁₂BrO₂^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	48.1 ± 2.5	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	23.9	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

+ 3 Ethanol = C₆H₁₈BrO₃^-

By formula: Br^- + 3C₂H₆O = C₆H₁₈BrO₃^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	39.7 ± 1.3	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	18.3	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

CH₆N⁺ + Ethanol = (CH₆N⁺ • Ethanol )

By formula: CH₆N⁺ + C₂H₆O = (CH₆N⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	89.1	kJ/mol	PHPMS	Meot-Ner, 1984	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	100.	J/mol*K	N/A	Meot-Ner, 1984	gas phase; Entropy change calculated or estimated; M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
37.	496.	PHPMS	Meot-Ner, 1984	gas phase; Entropy change calculated or estimated; M

CN^- + Ethanol = (CN^- • Ethanol )

By formula: CN^- + C₂H₆O = (CN^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	72.8 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Δ_rH°	73. ± 15.	kJ/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	94.1	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Δ_rS°	103.	J/mol*K	N/A	Larson and McMahon, 1987	gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	44.8 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B
Δ_rG°	41.8 ± 9.6	kJ/mol	IMRE	Larson and McMahon, 1987	gas phase; B,M

+ Ethanol = ( • Ethanol )

By formula: C₂H₃O₂^- + C₂H₆O = (C₂H₃O₂^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	86.6 ± 4.2	kJ/mol	N/A	Meot-Ner and Sieck, 1986	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	122.	J/mol*K	PHPMS	Meot-Ner and Sieck, 1986	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	49.8 ± 6.7	kJ/mol	TDAs	Meot-Ner and Sieck, 1986	gas phase; B

C₂H₄NO₂^- + Ethanol = C₄H₁₀NO₃^-

By formula: C₂H₄NO₂^- + C₂H₆O = C₄H₁₀NO₃^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	73.5 ± 2.1	kJ/mol	TDAs	Nieckarz, Atkins, et al., 2008	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	41. ± 4.2	kJ/mol	TDAs	Nieckarz, Atkins, et al., 2008	gas phase; B

C₂H₅O⁺ + Ethanol = (C₂H₅O⁺ • Ethanol )

By formula: C₂H₅O⁺ + C₂H₆O = (C₂H₅O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	123.	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	109.	J/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	90.8	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C₂H₅O^- + Ethanol = (C₂H₅O^- • Ethanol )

By formula: C₂H₅O^- + C₂H₆O = (C₂H₅O^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	115. ± 4.2	kJ/mol	TDEq	Meot-Ner and Sieck, 1986	gas phase; B,M
Δ_rH°	118. ± 10.	kJ/mol	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	112.	J/mol*K	PHPMS	Meot-Ner and Sieck, 1986	gas phase; M
Δ_rS°	123.	J/mol*K	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; switching reaction(CH3O-)CH3OH; Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	82.0 ± 6.7	kJ/mol	TDEq	Meot-Ner and Sieck, 1986	gas phase; B
Δ_rG°	79.5 ± 6.7	kJ/mol	IMRE	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Δ_rG°	84.1	kJ/mol	ICR	McIver, Scott, et al., 1973	gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; Meot-Ner (Mautner), 1992; M

C₂H₆FO^- + 2 Ethanol = C₄H₁₂FO₂^-

By formula: C₂H₆FO^- + 2C₂H₆O = C₄H₁₂FO₂^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	86.2 ± 1.3	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	50.63	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

C₂H₇O⁺ + Ethanol = (C₂H₇O⁺ • Ethanol )

By formula: C₂H₇O⁺ + C₂H₆O = (C₂H₇O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	134.	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Δ_rH°	135.	kJ/mol	ICR	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	119.	J/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Δ_rS°	119.	J/mol*K	N/A	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	98.3	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Δ_rG°	99.2	kJ/mol	ICR	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M

C₃H₇O^- + Ethanol = (C₃H₇O^- • Ethanol )

By formula: C₃H₇O^- + C₂H₆O = (C₃H₇O^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	115. ± 12.	kJ/mol	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	123.	J/mol*K	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	78.2 ± 8.4	kJ/mol	IMRE	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C₃H₉O⁺ + Ethanol = (C₃H₉O⁺ • Ethanol )

By formula: C₃H₉O⁺ + C₂H₆O = (C₃H₉O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	128.	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	120.	J/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	92.0	kJ/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C₃H₉O⁺ + Ethanol = (C₃H₉O⁺ • Ethanol )

By formula: C₃H₉O⁺ + C₂H₆O = (C₃H₉O⁺ • C₂H₆O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	133.	kJ/mol	ICR	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	118.	J/mol*K	N/A	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	98.3	kJ/mol	ICR	Bomse and Beauchamp, 1981	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M

C₃H₉Si⁺ + Ethanol = (C₃H₉Si⁺ • Ethanol )

By formula: C₃H₉Si⁺ + C₂H₆O = (C₃H₉Si⁺ • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	176.	kJ/mol	PHPMS	Wojtyniak and Stone, 1986	gas phase; switching reaction,Thermochemical ladder(CH3)3Si+))H2O, Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	127.	J/mol*K	N/A	Wojtyniak and Stone, 1986	gas phase; switching reaction,Thermochemical ladder(CH3)3Si+))H2O, Entropy change calculated or estimated; M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
117.	468.	PHPMS	Wojtyniak and Stone, 1986	gas phase; switching reaction,Thermochemical ladder(CH3)3Si+))H2O, Entropy change calculated or estimated; M

C₃H₉Sn⁺ + Ethanol = (C₃H₉Sn⁺ • Ethanol )

By formula: C₃H₉Sn⁺ + C₂H₆O = (C₃H₉Sn⁺ • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	146.	kJ/mol	PHPMS	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	135.	J/mol*K	N/A	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
74.9	525.	PHPMS	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

C₄H₉O^- + Ethanol = (C₄H₉O^- • Ethanol )

By formula: C₄H₉O^- + C₂H₆O = (C₄H₉O^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	111. ± 12.	kJ/mol	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	123.	J/mol*K	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	74.9 ± 8.4	kJ/mol	IMRE	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C₄H₁₂FO₂^- + 3 Ethanol = C₆H₁₈FO₃^-

By formula: C₄H₁₂FO₂^- + 3C₂H₆O = C₆H₁₈FO₃^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	65.27 ± 0.42	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	34.0	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

C₅H₁₁O^- + Ethanol = (C₅H₁₁O^- • Ethanol )

By formula: C₅H₁₁O^- + C₂H₆O = (C₅H₁₁O^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	110. ± 12.	kJ/mol	N/A	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	73.6 ± 8.4	kJ/mol	IMRE	Caldwell, Rozeboom, et al., 1984	gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

+ Ethanol = ( • Ethanol )

By formula: C₆H₅O^- + C₂H₆O = (C₆H₅O^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	80.8	kJ/mol	PHPMS	Meot-Ner and Sieck, 1986	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	113.	J/mol*K	PHPMS	Meot-Ner and Sieck, 1986	gas phase; M

+ Ethanol = C₈H₁₁O₂^-

By formula: C₆H₅O^- + C₂H₆O = C₈H₁₁O₂^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	80.8 ± 4.2	kJ/mol	N/A	Meot-Ner and Sieck, 1986	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	46.9 ± 6.7	kJ/mol	TDAs	Meot-Ner and Sieck, 1986	gas phase; B

+ Ethanol = ( • Ethanol )

By formula: Cl^- + C₂H₆O = (Cl^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	74.9 ± 1.7	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rH°	73.6 ± 2.1	kJ/mol	TDAs	Hiraoka, 1987	gas phase; B,B,M
Δ_rH°	72.4 ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	99.2	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Δ_rS°	96.7	J/mol*K	N/A	Larson and McMahon, 1984	gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	44.56	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	43.9 ± 8.4	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B
Δ_rG°	43.9 ± 8.4	kJ/mol	TDAs	Hiraoka, 1987	gas phase; B
Δ_rG°	43.5 ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1984	gas phase; B,M

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
41.8	295.	ICR	Riveros, 1974	gas phase; switching reaction(Cl-)CH3OH; Riveros, Breda, et al., 1973; M

( • Ethanol ) + Ethanol = ( • 2 Ethanol )

By formula: (Cl^- • C₂H₆O) + C₂H₆O = (Cl^- • 2C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	64.02 ± 0.84	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rH°	67.4 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	108.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	30.7	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	35. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 2 Ethanol ) + Ethanol = ( • 3 Ethanol )

By formula: (Cl^- • 2C₂H₆O) + C₂H₆O = (Cl^- • 3C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	58.2 ± 2.9	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rH°	53.6 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	108.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	21.6	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	21. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 3 Ethanol ) + Ethanol = ( • 4 Ethanol )

By formula: (Cl^- • 3C₂H₆O) + C₂H₆O = (Cl^- • 4C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	50.2 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	123.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	13. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 4 Ethanol ) + Ethanol = ( • 5 Ethanol )

By formula: (Cl^- • 4C₂H₆O) + C₂H₆O = (Cl^- • 5C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	48.1 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	128.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	9.6 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 5 Ethanol ) + Ethanol = ( • 6 Ethanol )

By formula: (Cl^- • 5C₂H₆O) + C₂H₆O = (Cl^- • 6C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	46.4 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	130.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.5 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 6 Ethanol ) + Ethanol = ( • 7 Ethanol )

By formula: (Cl^- • 6C₂H₆O) + C₂H₆O = (Cl^- • 7C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	41. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	113.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.1 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 7 Ethanol ) + Ethanol = ( • 8 Ethanol )

By formula: (Cl^- • 7C₂H₆O) + C₂H₆O = (Cl^- • 8C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	38. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	105.	J/mol*K	PHPMS	Hiraoka and Mizuse, 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.7 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; B

( • 8 Ethanol ) + Ethanol = ( • 9 Ethanol )

By formula: (Cl^- • 8C₂H₆O) + C₂H₆O = (Cl^- • 9C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	38. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; Estimated entropy; single temperature measurement; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	100.	J/mol*K	N/A	Hiraoka and Mizuse, 1987	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	6.3 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; Estimated entropy; single temperature measurement; B

( • 9 Ethanol ) + Ethanol = ( • 10 Ethanol )

By formula: (Cl^- • 9C₂H₆O) + C₂H₆O = (Cl^- • 10C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37. ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; Estimated entropy; single temperature measurement; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	100.	J/mol*K	N/A	Hiraoka and Mizuse, 1987	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	5.9 ± 4.2	kJ/mol	TDAs	Hiraoka and Mizuse, 1987	gas phase; Estimated entropy; single temperature measurement; B

+ Ethanol = C₂H₅D₆FO^-

By formula: F^- + C₂H₆O = C₂H₅D₆FO^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	99.2 ± 8.4	kJ/mol	IMRE	Wilkinson, Szulejko, et al., 1992	gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

+ Ethanol = ( • Ethanol )

By formula: F^- + C₂H₆O = (F^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	135.6 ± 2.9	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rH°	132. ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M
Δ_rH°	136. ± 9.2	kJ/mol	CIDT	DeTuri and Ervin, 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	104.	J/mol*K	N/A	Larson and McMahon, 1983	gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	103.5	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	101. ± 8.4	kJ/mol	IMRE	Larson and McMahon, 1983	gas phase; B,M

HS^- + Ethanol = (HS^- • Ethanol )

By formula: HS^- + C₂H₆O = (HS^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	68.20 ± 0.42	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B,M
Δ_rH°	67.8 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	79.5	J/mol*K	PHPMS	Sieck and Meot-ner, 1989	gas phase; M
Δ_rS°	82.8	J/mol*K	PHPMS	Meot-ner, 1988	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	44.4 ± 1.7	kJ/mol	TDAs	Sieck and Meot-ner, 1989	gas phase; B
Δ_rG°	43.1 ± 4.2	kJ/mol	TDAs	Meot-ner, 1988	gas phase; B

+ Ethanol = ( • Ethanol )

By formula: I^- + C₂H₆O = (I^- • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	54.39 ± 0.84	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rH°	50.6 ± 4.2	kJ/mol	TDAs	Caldwell and Kebarle, 1984	gas phase; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	79.1	J/mol*K	PHPMS	Caldwell and Kebarle, 1984	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	25.6	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Δ_rG°	27. ± 4.2	kJ/mol	TDAs	Caldwell and Kebarle, 1984	gas phase; B
Δ_rG°	25. ± 8.4	kJ/mol	IMRE	Tanabe, Morgon, et al., 1996	gas phase; Anchored to H2O..I- of Caldwell and Kebarle, 1984; B

+ 2 Ethanol = C₄H₁₂IO₂^-

By formula: I^- + 2C₂H₆O = C₄H₁₂IO₂^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	43.93 ± 0.84	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	18.5	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

+ 3 Ethanol = C₆H₁₈IO₃^-

By formula: I^- + 3C₂H₆O = C₆H₁₈IO₃^-

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	35.1 ± 2.1	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	14.7	kJ/mol	TDAs	Bogdanov, Peschke, et al., 1999	gas phase; B

+ Ethanol = ( • Ethanol )

By formula: Li⁺ + C₂H₆O = (Li⁺ • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	164. ± 7.9	kJ/mol	CIDT	Rodgers and Armentrout, 2000	RCD

+ Ethanol = ( • Ethanol )

By formula: Mg⁺ + C₂H₆O = (Mg⁺ • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	260. ± 20.	kJ/mol	ICR	Operti, Tews, et al., 1988	gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

+ Ethanol = ( • Ethanol )

By formula: Na⁺ + C₂H₆O = (Na⁺ • C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	110. ± 5.4	kJ/mol	CIDC	Amicangelo and Armentrout, 2001	Anchor NH3=24.41; RCD
Δ_rH°	102. ± 4.	kJ/mol	CIDT	Armentrout and Rodgers, 2000	RCD
Δ_rH°	102. ± 4.	kJ/mol	CIDT	Rodgers and Armentrout, 1999	RCD

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
79.5	298.	IMRE	McMahon and Ohanessian, 2000	Anchor alanine=39.89; RCD
0.0	0.	CIDT	Rodgers and Armentrout, 1999	RCD

( • Ethanol ) + Ethanol = ( • 2 Ethanol )

By formula: (Na⁺ • C₂H₆O) + C₂H₆O = (Na⁺ • 2C₂H₆O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	99.2 ± 6.7	kJ/mol	CIDC	Amicangelo and Armentrout, 2001	Anchor NH3=24.41; RCD
Δ_rH°	96.7 ± 4.6	kJ/mol	CIDC	Amicangelo and Armentrout, 2001	Anchor NH3=24.41; RCD
Δ_rH°	99.2 ± 6.7	kJ/mol	CIDC	Amicangelo and Armentrout, 2001	Anchor NH3=24.41; RCD
Δ_rH°	97.5 ± 5.9	kJ/mol	CIDC	Amicangelo and Armentrout, 2001	Anchor NH3=24.41; RCD

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Notes

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Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P., Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements, J. Am. Chem. Soc., 1984, 106, 967. [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]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Amicangelo and Armentrout, 2001
Amicangelo, J.C.; Armentrout, P.B., Relative and Absolute Bond Dissociation Energies of Sodium Cation Complexes Determined Using Competitive Collision-Induced Dissociation Experiments, Int. J. Mass Spectrom., 2001, 212, 1-3, 301, https://doi.org/10.1016/S1387-3806(01)00494-8 . [all data]

Armentrout and Rodgers, 2000
Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [all data]

Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B., Absolute Binding Energies of Sodium Ions to Short-Chain Alcohols, CnH2n+2O, n=1-4, Determined by Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory, 1999, 4955. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
IE (evaluated)	Recommended ionization energy
P_c	Critical pressure
T	Temperature
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
V_c	Critical volume
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions
ρ_c	Critical density

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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