Methylene chloride
- Formula: CH2Cl2
- Molecular weight: 84.933
- IUPAC Standard InChIKey: YMWUJEATGCHHMB-UHFFFAOYSA-N
- CAS Registry Number: 75-09-2
- 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: Methane, dichloro-; Aerothene MM; Dichloromethane; Freon 30; Methylene dichloride; Narkotil; Solaesthin; Solmethine; CH2Cl2; Methane dichloride; Methylene bichloride; Chlorure de methylene; Metylenu chlorek; NCI-C50102; R 30; Rcra waste number U080; UN 1593; Methoklone; Salesthin; F 30; F 30 (chlorocarbon); HCC 30; Khladon 30; Metaclen; NSC 406122; Soleana VDA
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -95.52 | kJ/mol | Review | Chase, 1998 | Data last reviewed in December, 1968 |
ΔfH°gas | -95.1 ± 2.5 | kJ/mol | Review | Manion, 2002 | derived from recommended ΔfHliquid° and ΔvapH°; DRB |
ΔfH°gas | -95.7 ± 1.3 | kJ/mol | Chyd | Lacher, Amador, et al., 1967 | Reanalyzed by Cox and Pilcher, 1970, Original value = -96.0 ± 1.3 kJ/mol; At 250 C; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas,1 bar | 270.28 | J/mol*K | Review | Chase, 1998 | Data last reviewed in December, 1968 |
Gas Phase Heat Capacity (Shomate Equation)
Cp° = A + B*t + C*t2 + D*t3 +
E/t2
H° − H°298.15= A*t + B*t2/2 +
C*t3/3 + D*t4/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t2/2 + D*t3/3 −
E/(2*t2) + G
Cp = heat capacity (J/mol*K)
H° = standard enthalpy (kJ/mol)
S° = standard entropy (J/mol*K)
t = temperature (K) / 1000.
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Temperature (K) | 298. to 1200. | 1200. to 6000. |
---|---|---|
A | 19.17351 | 95.12993 |
B | 136.8444 | 6.721722 |
C | -95.12993 | -1.288196 |
D | 26.03105 | 0.085646 |
E | -0.119405 | -14.93885 |
F | -106.9338 | -157.3506 |
G | 256.0144 | 340.5412 |
H | -95.52114 | -95.52114 |
Reference | Chase, 1998 | Chase, 1998 |
Comment | Data last reviewed in December, 1968 | Data last reviewed in December, 1968 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
DRB - Donald R. Burgess, Jr.
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 | -124.1 ± 2.5 | kJ/mol | Review | Manion, 2002 | adopted combustion calorimetry data of Hu and Sinke, 1969 with increased uncertainty to reflect other data; DRB |
ΔfH°liquid | -124.3 | kJ/mol | Ccr | Hu and Sinke, 1969, 2 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -602.50 | kJ/mol | Ccr | Hu and Sinke, 1969, 2 | ALS |
ΔcH°liquid | -605.8 ± 8.4 | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -605. ± 4. kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 174.5 | J/mol*K | N/A | Moseeva, Rabinovich, et al., 1978 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
102.3 | 298.15 | Moseeva, Rabinovich, et al., 1978 | T = 5 to 300 K.; DH |
105.5 | 303.2 | Harrison and Moelwyn-Hughes, 1957 | T = 244 to 303 K. Unsmoothed experimental datum.; DH |
129.3 | 298. | Kurbatov, 1948 | T = -76 to 41°C. Mean Cp, four temperatures.; DH |
100.0 | 298. | Riedel, 1941 | T = -47 to 41°C.; DH |
100.0 | 298.1 | Riedel, 1940 | T = -47 to 41°C.; DH |
100.5 | 292.5 | Perlick, 1937 | T = -58 to 19°C. Value is unsmoothed experimental datum.; DH |
100.8 | 292.5 | Perlick, 1937, 2 | T = -58 to 19°C. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tboil | 313. ± 1. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 198.06 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 176. | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 177. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 176.65 | K | N/A | Timmermans, 1934 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 508. | K | N/A | Garcia-Sanchez, Romero-Martinez, et al., 1989 | Uncertainty assigned by TRC = 0.2 K; mean of 5 determinations, direct observation of meniscus; TRC |
Tc | 510. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 63.55 | bar | N/A | Garcia-Sanchez, Romero-Martinez, et al., 1989 | Uncertainty assigned by TRC = 0.15 bar; mean of 5 determinations, measurement of P at Tc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 29. | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 29.03 ± 0.08 | kJ/mol | Review | Manion, 2002 | adopted Majer, Svab, et al., 1980 value plus a correction for non-ideality; DRB |
ΔvapH° | 30.6 ± 0.1 | kJ/mol | C | An and Hu, 1989 | AC |
ΔvapH° | 28.8 | kJ/mol | C | Majer, Sváb, et al., 1980 | AC |
ΔvapH° | 28.5 ± 0.42 | kJ/mol | V | Mathews, 1926 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 27.7 ± 0.96 kJ/mol; ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
28.06 | 313. | N/A | Majer and Svoboda, 1985 | |
30.2 | 248. | N/A | Ganeff and Jungers, 2010 | Based on data from 233. to 313. K.; AC |
29.0 | 326. | A | Stephenson and Malanowski, 1987 | Based on data from 311. to 383. K.; AC |
30.3 | 279. | EB | Boublík and Aim, 1972 | Based on data from 264. to 311. K.; AC |
29.2 | 308. | N/A | Mueller and Ignatowski, 1960 | Based on data from 303. to 313. K.; AC |
29.4 | 186. to 312. | N/A | Perry, 1926 | AC |
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 |
---|---|---|---|---|---|
303.14 to 313.14 | 3.97323 | 1016.865 | -56.623 | Mueller and Ignatowski, 1960, 2 | Coefficents calculated by NIST from author's data. |
233. to 313. | 4.53691 | 1327.016 | -20.474 | Ganeff and Jungers, 1948 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.160 | 178.22 | Moseeva, Rabinovich, et al., 1978 | DH |
6.16 | 178.2 | Domalski and Hearing, 1996 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões
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
CHCl2- + =
By formula: CHCl2- + H+ = CH2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1572. ± 9.2 | kJ/mol | G+TS | Born, Ingemann, et al., 2000 | gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B |
ΔrH° | 1567. ± 13. | kJ/mol | G+TS | Bohme, Lee-Ruff, et al., 1972 | gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1540. ± 8.4 | kJ/mol | IMRE | Born, Ingemann, et al., 2000 | gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B |
ΔrG° | 1543.9 ± 2.9 | kJ/mol | IMRE | Poutsma, Paulino, et al., 1997 | gas phase; relative to tBuOH at ΔGacid = 369.3; B |
ΔrG° | 1535. ± 13. | kJ/mol | IMRB | Bohme, Lee-Ruff, et al., 1972 | gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B |
By formula: Cl- + CH2Cl2 = (Cl- • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.1 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
ΔrH° | 61.9 ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
ΔrH° | 64.9 ± 1.3 | kJ/mol | TDEq | Dougherty, Dalton, et al., 1974 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92.5 | J/mol*K | N/A | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; Kebarle, 1977; M |
ΔrS° | 92.0 | J/mol*K | HPMS | Dougherty, Dalton, et al., 1974 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 38. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
ΔrG° | 37.0 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
ΔrG° | 37.2 ± 2.5 | kJ/mol | TDEq | Dougherty, Dalton, et al., 1974 | gas phase; B |
By formula: CN- + CH2Cl2 = (CN- • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 68. ± 15. | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 101. | 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 |
ΔrG° | 38. ± 9.6 | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
By formula: C2H5+ + CH2Cl2 = (C2H5+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 151. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 189. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; Entropy change is questionable; M |
By formula: 2H2 + CH2Cl2 = CH4 + 2HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -163.4 ± 1.3 | kJ/mol | Chyd | Lacher, Amador, et al., 1967 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -167.7 ± 1.3 kJ/mol; At 250 C; ALS |
By formula: CH2Cl3- + 2CH2Cl2 = C2H4Cl5-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.81 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C2H4Cl5- + 3CH2Cl2 = C3H6Cl7-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40.6 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 19.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C3H6Cl7- + 4CH2Cl2 = C4H8Cl9-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.7 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 15.2 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
C4H8Cl9- + 5 = C5H10Cl11-
By formula: C4H8Cl9- + 5CH2Cl2 = C5H10Cl11-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.2 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 11.0 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C3H7+ + CH2Cl2 = (C3H7+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 65.3 | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C6H11+ + CH2Cl2 = (C6H11+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 44.4 | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: Li+ + CH2Cl2 = (Li+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. | kJ/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M |
By formula: C4H9+ + CH2Cl2 = (C4H9+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 93.3 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C5H11+ + CH2Cl2 = (C5H11+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 97.5 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C5H9+ + CH2Cl2 = (C5H9+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 41. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84.5 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
C14H21MnO2 (solution) + (solution) = C8H7Cl2MnO2 (solution) +
(solution)
By formula: C14H21MnO2 (solution) + CH2Cl2 (solution) = C8H7Cl2MnO2 (solution) + C7H16 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -37.7 ± 4.2 | kJ/mol | PAC | Yang and Yang, 1992 | solvent: Heptane; MS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering 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:
L - 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.33 ± 0.04 | eV | N/A | N/A | L |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
628. ± 8. | Cacace, de Petris, et al., 1999 | COS; C2H2. Paper reports PA although proton transfer reactivity brackets GB. Following authors, the GBs of CH2Cl2 and COS are equated given reversible proton transfer.; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
602. ± 8. | Cacace, de Petris, et al., 1999 | COS; C2H2. Paper reports PA although proton transfer reactivity brackets GB. Following authors, the GBs of CH2Cl2 and COS are equated given reversible proton transfer.; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.32 | PE | Von Niessen, Asbrink, et al., 1982 | LBLHLM |
11.40 | PE | Kimura, Katsumata, et al., 1981 | LLK |
11.32 ± 0.01 | PI | Werner, Tsai, et al., 1974 | LLK |
11.28 | EI | Lossing, 1972 | LLK |
11.33 | PE | Dewar and Worley, 1969 | RDSH |
11.36 | CI | Cermak, 1968 | RDSH |
11.35 ± 0.02 | PI | Watanabe, 1957 | RDSH |
11.40 | PE | Dixon, Murrell, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C+ | 25.5 ± 0.1 | ? | EI | Reed and Snedden, 1956 | RDSH |
CH+ | 21.72 ± 0.04 | ? | EI | Reed and Snedden, 1956 | RDSH |
CHCl2+ | 13.00 ± 0.10 | H | EI | Reed and Snedden, 1956 | RDSH |
CH2+ | 17.0 | Cl2 | EI | Haney and Franklin, 1968 | RDSH |
CH2Cl+ | 12.10 | Cl | EI | Holmes, Lossing, et al., 1988 | LL |
CH2Cl+ | 12.14 ± 0.02 | Cl | PI | Werner, Tsai, et al., 1974 | LLK |
CH2Cl+ | 12.15 | Cl | EI | Lossing, 1972 | LLK |
CH2Cl+ | 12.1 ± 0.1 | Cl | EI | Harrison and Shannon, 1962 | RDSH |
CH2Cl+ | 12.89 ± 0.03 | Cl | EI | Reed and Snedden, 1956 | RDSH |
CHC12+ | 12.12 ± 0.05 | H | EI | Martin, Lampe, et al., 1966 | RDSH |
Cl+ | 17.4 ± 0.1 | CH2Cl | EI | DeCorpo, Bafus, et al., 1971 | LLK |
Cl+ | 17.4 | CH2Cl | EI | Franklin and Haney, 1970 | RDSH |
De-protonation reactions
CHCl2- + =
By formula: CHCl2- + H+ = CH2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1572. ± 9.2 | kJ/mol | G+TS | Born, Ingemann, et al., 2000 | gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B |
ΔrH° | 1567. ± 13. | kJ/mol | G+TS | Bohme, Lee-Ruff, et al., 1972 | gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1540. ± 8.4 | kJ/mol | IMRE | Born, Ingemann, et al., 2000 | gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B |
ΔrG° | 1543.9 ± 2.9 | kJ/mol | IMRE | Poutsma, Paulino, et al., 1997 | gas phase; relative to tBuOH at ΔGacid = 369.3; B |
ΔrG° | 1535. ± 13. | kJ/mol | IMRB | Bohme, Lee-Ruff, et al., 1972 | gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: CH2Cl3- + 2CH2Cl2 = C2H4Cl5-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.81 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: CN- + CH2Cl2 = (CN- • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 68. ± 15. | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 101. | 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 |
ΔrG° | 38. ± 9.6 | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
By formula: C2H4Cl5- + 3CH2Cl2 = C3H6Cl7-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40.6 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 19.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C2H5+ + CH2Cl2 = (C2H5+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 151. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 189. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; Entropy change is questionable; M |
By formula: C3H6Cl7- + 4CH2Cl2 = C4H8Cl9-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.7 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 15.2 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C3H7+ + CH2Cl2 = (C3H7+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 65.3 | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
C4H8Cl9- + 5 = C5H10Cl11-
By formula: C4H8Cl9- + 5CH2Cl2 = C5H10Cl11-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.2 | kJ/mol | N/A | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 11.0 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
By formula: C4H9+ + CH2Cl2 = (C4H9+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 93.3 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C5H9+ + CH2Cl2 = (C5H9+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 41. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 84.5 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C5H11+ + CH2Cl2 = (C5H11+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 97.5 | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: C6H11+ + CH2Cl2 = (C6H11+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 44.4 | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; M |
By formula: Cl- + CH2Cl2 = (Cl- • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.1 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
ΔrH° | 61.9 ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
ΔrH° | 64.9 ± 1.3 | kJ/mol | TDEq | Dougherty, Dalton, et al., 1974 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92.5 | J/mol*K | N/A | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; Kebarle, 1977; M |
ΔrS° | 92.0 | J/mol*K | HPMS | Dougherty, Dalton, et al., 1974 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 38. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
ΔrG° | 37.0 | kJ/mol | TDAs | Hiraoka, Mizuno, et al., 2001 | gas phase; B |
ΔrG° | 37.2 ± 2.5 | kJ/mol | TDEq | Dougherty, Dalton, et al., 1974 | gas phase; B |
By formula: Li+ + CH2Cl2 = (Li+ • CH2Cl2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. | kJ/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chase, 1998
Chase, M.W., Jr.,
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Cox and Pilcher, 1970
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Hu and Sinke, 1969
Hu, A.T.; Sinke, G.C.,
Combustion calorimetry of some chlorinated organic compounds,
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Combustion calorimetry of some chlorinated organic compounds,
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Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H.,
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Riedel, L.,
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Perlick, A.,
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Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
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Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Timmermans, 1935
Timmermans, J.,
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Timmermans, 1934
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Majer and Svoboda, 1985
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Majer, Svab, et al., 1980
Majer, V.; Svab, L.; Svoboda, V.,
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Majer, Sváb, et al., 1980
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Enthalpies of vaporization and cohesive energies for a group of chlorinated hydrocarbons,
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Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
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Pedley, Naylor, et al., 1986
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Ganeff and Jungers, 2010
Ganeff, Jean M.; Jungers, Joseph C.,
Tensions de vapeur du système CH3Cl «63743» CH2Cl2,
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. [all data]
Stephenson and Malanowski, 1987
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Boublík and Aim, 1972
Boublík, T.; Aim, K.,
Heats of vaporization of simple non-spherical molecule compounds,
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Mueller and Ignatowski, 1960
Mueller, Charles R.; Ignatowski, Albert J.,
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Perry, 1926
Perry, J.H.,
The Vapor Pressures of Methylene Chloride,
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Mueller and Ignatowski, 1960, 2
Mueller, C.R.; Ignatowski, A.J.,
Equilibrium and Transport Properties of the Carbon Tetrachloride-Methylene Chloride System,
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Ganeff and Jungers, 1948
Ganeff, J.M.; Jungers, J.C.,
Tensions de Vapeur du Systeme CH3Cl - CH2Cl2,
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Domalski and Hearing, 1996
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Born, M.; Ingemann, S.; Nibbering, N.M.M.,
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. [all data]
Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B.,
Acidity order of selected bronsted acids in the gas phase at 300K,
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Poutsma, Paulino, et al., 1997
Poutsma, J.C.; Paulino, J.A.; Squires, R.R.,
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Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria,
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Hiraoka, K.; Mizuno, T.; Iino, T.; Eguchi, D.; Yamabe, S.,
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. [all data]
Dougherty, Dalton, et al., 1974
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SN2 reactions in the gas phase: Structure of the transition state,
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Kebarle, 1977
Kebarle, P.,
Ion Thermochemistry and Solvation from Gas Phase Ion Equilibria,
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Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids,
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Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P.,
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Sharma, Meza de Hojer, et al., 1985
Sharma, D.M.S.; Meza de Hojer, S.; Kebarle, P.,
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Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L.,
Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases,
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Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P.,
Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n,
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Von Niessen, Asbrink, et al., 1982
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Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLIV. Ionization potentials bond dissociation energies for chloro-and fluoromethyl radicals,
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Cermak, V.,
Penning ionization electron spectroscopy. I. Determination of ionization potentials of polyatomic molecules,
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Watanabe, K.,
Ionization potentials of some molecules,
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The photoelectron spectra of the halomethanes,
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Reed, R.I.; Snedden, W.,
Studies in electron impact methods. Part 6.-The formation of the methine and carbon ions,
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Haney, M.A.; Franklin, J.L.,
Correlation of excess energies of electron-impact dissociations with the translational energies of the products,
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Harrison, A.G.; Shannon, T.W.,
An electron impact study of chloromethyl and dichloromethyl derivatives,
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Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W.,
An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes,
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DeCorpo, Bafus, et al., 1971
DeCorpo, J.J.; Bafus, D.A.; Franklin, J.L.,
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Franklin, J.L.; Haney, M.A.,
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Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°gas,1 bar Entropy of gas at standard conditions (1 bar) S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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 ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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