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Benzyl chloride

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Deltafgas4.5 ± 0.8kcal/molCmKirkbride, 1956heat of formation derived by Cox and Pilcher, 1970

Condensed phase thermochemistry data

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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:
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
Deltafliquid-7.8 ± 0.6kcal/molCmKirkbride, 1956heat of formation derived by Cox and Pilcher, 1970; ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.59298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH

Phase change data

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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
Tboil452. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus233.95KN/ATimmermans and Hennaut-Roland, 1935Uncertainty assigned by TRC = 0.3 K; TRC
Tfus233.45KN/ASmith and Andrews, 1931, 2Uncertainty assigned by TRC = 0.4 K; freezing point by thermocouple; TRC
Tfus225.3KN/AAltschul and Von Schneider, 1895Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap12.0 ± 0.07kcal/molGSKrasnykh, Vasiltsova, et al., 2002Based on data from 276. - 309. K.; AC
Deltavap11.9kcal/molCGCKrasnykh, Vasiltsova, et al., 2002AC
Deltavap12.0 ± 0.1kcal/molN/AAshcroft, 1976See also Dykyj, Svoboda, et al., 1999.; AC
Deltavap12.3 ± 0.4kcal/molVKirkbride, 1956heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
11.6335.A,IStephenson and Malanowski, 1987Based on data from 320. - 390. K. See also Ashcroft, 1976.; AC
11.6310.AStephenson and Malanowski, 1987Based on data from 295. - 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. - 452.64.676921932.142-39.396Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
2.09230.DSCAhmed and Eades, 1972AC

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:


Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

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

C7H6Cl- + Hydrogen cation = Benzyl chloride

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar396.6 ± 1.6kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes
Quantity Value Units Method Reference Comment
Deltar388.8 ± 1.7kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes

C7H6Cl- + Hydrogen cation = Benzyl chloride

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar372.0 ± 2.1kcal/molG+TSPoutsma, Nash, et al., 1997gas phase
Quantity Value Units Method Reference Comment
Deltar364.9 ± 2.0kcal/molIMRBPoutsma, Nash, et al., 1997gas phase

Henry's Law data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
1.6 LN/A

Gas phase ion energetics data

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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 ± 0.02PITraeger and Kompe, 1990LL
9.14 ± 0.01PIPonomarev, Takhimova, et al., 1974LLK
9.14 ± 0.01PIAkopyan, Vilesov, et al., 1972LLK
9.10 ± 0.05PIAkopyan and Vilesov, 1966RDSH
9.30PEZverev and Ermolaeva, 1981Vertical value; LLK
9.29PEKimura, Katsumata, et al., 1981Vertical value; LLK
9.30PESchmidt and Schweig, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+9.85 ± 0.02ClPITraeger and Kompe, 1990LL
C7H7+10.16 ± 0.05ClPIAkopyan, Vilesov, et al., 1972LLK
C7H7+10.40 ± 0.05ClPIAkopyan and Vilesov, 1966RDSH

De-protonation reactions

C7H6Cl- + Hydrogen cation = Benzyl chloride

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar396.6 ± 1.6kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar388.8 ± 1.7kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C7H6Cl- + Hydrogen cation = Benzyl chloride

By formula: C7H6Cl- + H+ = C7H7Cl

Quantity Value Units Method Reference Comment
Deltar372.0 ± 2.1kcal/molG+TSPoutsma, Nash, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Deltar364.9 ± 2.0kcal/molIMRBPoutsma, Nash, et al., 1997gas phase; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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Mass spectrum
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Additional Data

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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.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 69
NIST MS number 228675

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Doleib and Iskander, 1967
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 4065
Instrument n.i.g.
Melting point -45
Boiling point 179

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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, 3644-3660. [all data]

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, 2
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]

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]

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]

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]

Doleib and Iskander, 1967
Doleib, D.M.; Iskander, Y., The influence of the nitro-group upon side-chain reactivity. Part IV. The inhibition of «alpha»-proton extraction from 4-nitrobenzyl chloride by the steric effect of methyl groups in the 3- and 5-positions, J. Chem. Soc. B:, 1967, 1154-1158. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References