Benzene, 1-chloro-2-methyl-
- Formula: C7H7Cl
- Molecular weight: 126.583
- IUPAC Standard InChIKey: IBSQPLPBRSHTTG-UHFFFAOYSA-N
- CAS Registry Number: 95-49-8
- 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. - Species with the same structure:
- Other names: Toluene, o-chloro-; o-Chlorotoluene; o-Tolyl chloride; 1-Methyl-2-chlorobenzene; 2-Chloro-1-methylbenzene; 2-Chlorotoluene; 1-Chloro-2-methylbenzene; ortho-Chlorotoluene; Halso 99; 2-Methylchlorobenzene; NSC 8766
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
ΔcH°liquid | -895. ± 3. | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | At 291.7 °K |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 432.1 ± 0.9 | K | AVG | N/A | Average of 12 out of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 238. ± 2. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.8 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 345. to 430. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 9.19 ± 0.01 | kcal/mol | V | Mathews, 1926 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.94 | 385. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 370. to 432. K.; AC |
10.2 | 353. | A | Stephenson and Malanowski, 1987 | Based on data from 338. to 493. K. See also Kkykj and Repas, 1973 and Dykyj and Vanko, 1970.; AC |
10.2 | 361. | N/A | Boublik, Fried, et al., 1984 | Based on data from 345. to 430. K.; AC |
10.7 | 293. | N/A | Stull, 1947 | Based on data from 278. to 432. K.; AC |
10.9 | 288. | N/A | Stuckey and Saylor, 1940 | Based on data from 273. to 348. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
278.6 to 432.5 | 4.48170 | 1768.105 | -38.389 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.46 | 237. | DSC | Ahmed and Eades, 1972 | AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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
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
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.72 ± 0.11 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 188.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 181.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.62 | PE | Baidin, Misharev, et al., 1985 | LBLHLM |
8.7 ± 0.1 | EI | Tajima and Tsuchiya, 1972 | LLK |
8.83 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
8.97 | PE | Baidin, Misharev, et al., 1985 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 15.7 ± 0.2 | C2H2+Cl | EI | Tajima and Tsuchiya, 1973 | LLK |
C5H5+ | 15.67 ± 0.015 | C2H2+Cl | EI | Tajima and Tsuchiya, 1972 | LLK |
C7H6Cl+ | 12.18 ± 0.09 | H | EI | Selim, Rabbih, et al., 1994 | LL |
C7H7+ | 11.17 ± 0.05 | Cl | EI | Selim, Rabbih, et al., 1994 | LL |
C7H7+ | 11.2 ± 0.1 | ? | EI | Tajima and Tsuchiya, 1972 | LLK |
C7H7+ | 11.8 | Cl | EI | Yeo and Williams, 1970 | RDSH |
De-protonation reactions
C7H6Cl- + =
By formula: C7H6Cl- + H+ = C7H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 373.6 ± 3.1 | kcal/mol | G+TS | Wenthold, Wierschke, et al., 1994 | gas phase; Between MeOCH2CH2OH and tBuCH2OH, near CH2Cl2; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.5 ± 3.0 | kcal/mol | IMRB | Wenthold, Wierschke, et al., 1994 | gas phase; Between MeOCH2CH2OH and tBuCH2OH, near CH2Cl2; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 2538 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H.,
Heats of combustion of organic chloro compounds determined by the "quartz wool" method,
Acta Chem. Scand., 1953, 7, 65. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
J. Am. Chem. Soc., 1926, 48, 562-576. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Kkykj and Repas, 1973
Kkykj, J.; Repas, M.,
Petrochemia, 1973, 13, 179. [all data]
Dykyj and Vanko, 1970
Dykyj, J.; Vanko, A.,
Petrochemica, 1970, 10, 1, 3. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Stuckey and Saylor, 1940
Stuckey, James M.; Saylor, John H.,
The Vapor Pressures of Some Organic Compounds. I. 1,
J. Am. Chem. Soc., 1940, 62, 11, 2922-2925, https://doi.org/10.1021/ja01868a011
. [all data]
Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G.,
Proton magnetic relaxation in toluene and some derivatives,
J. Chem. Soc., Faraday Trans. 2, 1972, 68, 1623, https://doi.org/10.1039/f29726801623
. [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]
Baidin, Misharev, et al., 1985
Baidin, V.N.; Misharev, A.D.; Takhistov, V.V.,
Effect of alkyl substituents on the ionization potentials of halogenobenzenes,
Zh. Org. Khim., 1985, 21, 817. [all data]
Tajima and Tsuchiya, 1972
Tajima, S.; Tsuchiya, T.,
The effects of the repeller voltage and the shield voltage on appearance potential measurements by electron impact,
Shitsuryo Bunseki, 1972, 20, 117. [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]
Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T.,
Energetics consideration of C5H5+ ions produced from various precursors by electron impact,
Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]
Selim, Rabbih, et al., 1994
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F.,
Loss of H and Cl from the molecular ions of chlorotoluene isomers using electron impact mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1994, 134, 119. [all data]
Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H.,
Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer,
Chem. Commun., 1970, 886. [all data]
Wenthold, Wierschke, et al., 1994
Wenthold, P.G.; Wierschke, S.G.; Nash, J.J.; Squires, R.R.,
Biradical thermochemistry from collision-induced dissociation threshold energy measurements .2. Experimental and theoretical studies of the Mechanism and Thermochemistry of Formation of alph,
J. Am. Chem. Soc., 1994, 116, 16, 7378, https://doi.org/10.1021/ja00095a048
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy 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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