Benzyl chloride
- Formula: C7H7Cl
- Molecular weight: 126.583
- IUPAC Standard InChIKey: KCXMKQUNVWSEMD-UHFFFAOYSA-N
- CAS Registry Number: 100-44-7
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Benzene, (chloromethyl)-; Toluene, α-chloro-; α-Chlorotoluene; ω-Chlorotoluene; (Chloromethyl)benzene; Chlorophenylmethane; C6H5CH2Cl; α-Chlortoluol; Benzile (cloruro di); Benzylchlorid; Benzyle (chlorure de); Chlorure de benzyle; NCI-C06360; Rcra waste number P028; UN 1738; Phenylmethyl chloride; NSC 8043; Tolyl chloride
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Phase change data
Go To: Top, 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:
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 | 452. ± 3. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 233.95 | K | N/A | Timmermans and Hennaut-Roland, 1935 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 233.45 | K | N/A | Smith and Andrews, 1931 | Uncertainty assigned by TRC = 0.4 K; freezing point by thermocouple; TRC |
Tfus | 225.3 | K | N/A | Altschul and Von Schneider, 1895 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.0 ± 0.07 | kcal/mol | GS | Krasnykh, Vasiltsova, et al., 2002 | Based on data from 276. to 309. K.; AC |
ΔvapH° | 11.9 | kcal/mol | CGC | Krasnykh, Vasiltsova, et al., 2002 | AC |
ΔvapH° | 12.0 ± 0.1 | kcal/mol | N/A | Ashcroft, 1976 | See also Dykyj, Svoboda, et al., 1999.; AC |
ΔvapH° | 12.3 ± 0.4 | kcal/mol | V | Kirkbride, 1956 | heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.6 | 335. | A,I | Stephenson and Malanowski, 1987 | Based on data from 320. to 390. K. See also Ashcroft, 1976.; AC |
11.6 | 310. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 453. K. See also Stull, 1947.; 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 |
---|---|---|---|---|---|
295. to 452.6 | 4.67692 | 1932.142 | -39.396 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.09 | 230. | DSC | Ahmed and Eades, 1972 | AC |
Gas phase ion energetics data
Go To: Top, Phase change 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
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.10 ± 0.02 | PI | Traeger and Kompe, 1990 | LL |
9.14 ± 0.01 | PI | Ponomarev, Takhimova, et al., 1974 | LLK |
9.14 ± 0.01 | PI | Akopyan, Vilesov, et al., 1972 | LLK |
9.10 ± 0.05 | PI | Akopyan and Vilesov, 1966 | RDSH |
9.30 | PE | Zverev and Ermolaeva, 1981 | Vertical value; LLK |
9.29 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
9.30 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 9.85 ± 0.02 | Cl | PI | Traeger and Kompe, 1990 | LL |
C7H7+ | 10.16 ± 0.05 | Cl | PI | Akopyan, Vilesov, et al., 1972 | LLK |
C7H7+ | 10.40 ± 0.05 | Cl | PI | Akopyan and Vilesov, 1966 | RDSH |
De-protonation reactions
C7H6Cl- + =
By formula: C7H6Cl- + H+ = C7H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 396.6 ± 1.6 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 388.8 ± 1.7 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
C7H6Cl- + =
By formula: C7H6Cl- + H+ = C7H7Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372.0 ± 2.1 | kcal/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 364.9 ± 2.0 | kcal/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Timmermans and Hennaut-Roland, 1935
Timmermans, J.; Hennaut-Roland, M.,
Physical constants of 20 organic compounds. VII.,
J. Chim. Phys. Phys.-Chim. Biol., 1935, 32, 501. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal Energy Studies I. Phenyl Derivatives of Methane, Ethane and Some Related Compounds,
J. Am. Chem. Soc., 1931, 53, 3644. [all data]
Altschul and Von Schneider, 1895
Altschul, M.; Von Schneider, B.,
Freezing points of some organic fluids,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 24. [all data]
Krasnykh, Vasiltsova, et al., 2002
Krasnykh, Eugen L.; Vasiltsova, Tatiana V.; Verevkin, Sergey P.; Heintz, Andreas,
Vapor Pressures and Enthalpies of Vaporization of Benzyl Halides and Benzyl Ethers,
J. Chem. Eng. Data, 2002, 47, 6, 1372-1378, https://doi.org/10.1021/je020034h
. [all data]
Ashcroft, 1976
Ashcroft, Stanley J.,
Vapor pressures and enthalpies of vaporization of benzyl halides,
J. Chem. Eng. Data, 1976, 21, 4, 397-398, https://doi.org/10.1021/je60071a009
. [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]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
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]
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]
Traeger and Kompe, 1990
Traeger, J.C.; Kompe, B.M.,
Threshold C7H7 formation from the benzyl halides by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1990, 101, 111. [all data]
Ponomarev, Takhimova, et al., 1974
Ponomarev, D.A.; Takhimova, V.V.; Akopyan, M.E.; Sergeyev, Y.L.,
Effect of alkyl groups on the stability of cations in the absence of solvation effects,
Zh. Org. Khim., 1974, 10, 403. [all data]
Akopyan, Vilesov, et al., 1972
Akopyan, M.E.; Vilesov, F.I.; Lopatin, S.N.,
Photoionization of benzyl chloride,
Khim. Vys. Energ., 1972, 6, 110. [all data]
Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I.,
A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A,
Zh. Fiz. Khim., 1966, 40, 125, In original 63. [all data]
Zverev and Ermolaeva, 1981
Zverev, V.V.; Ermolaeva, L.V.,
Ionization potentials and intramolecular charge transfer. II. The photoelectron spectrum and electronic structure of trichloromethylbenzene,
Zh. Strukt. Khim., 1981, 22, 22. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A.,
C-Hal hyperkonjugation,
Tetrahedron Lett., 1973, 981. [all data]
Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R.,
Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method,
J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105
. [all data]
Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R.,
Absolute Heats of Formation of Phenylcarbene and Vinylcarbene,
J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point 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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