Benzene, 1-fluoro-2-methyl-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δcliquid-903.2kcal/molCcbSwarts, 1919Not corrected for CODATA value of ΔfH

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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil387.KN/APCR Inc., 1990BS
Tboil387.2KN/AWeast and Grasselli, 1989BS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
303.20.034Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
10.0263.N/ADykyj, Svoboda, et al., 1999Based on data from 248. to 388. K.; AC
7.53465.N/ADykyj, Svoboda, et al., 1999Based on data from 452. to 531. K.; AC
9.25310.AStephenson and Malanowski, 1987Based on data from 295. to 388. K. See also Potter and Saylor, 1951.; AC
7.72468.N/AMousa, 1984Based on data from 453. to 530. K.; AC
9.08323.N/AMozhginskay and Kolysko, 1974Based on data from 308. to 348. K. See also Boublik, Fried, et al., 1984.; AC
9.68264.N/AStull, 1947Based on data from 248. to 387. 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
249.0 to 387.4.255901457.699-44.628Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
2.342210.65N/AMeva'a and Lichanot, 1990DH
2.3210.7N/ADomalski and Hearing, 1996AC
2.3204.DSCAhmed and Eades, 1972AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.0210.65Meva'a and Lichanot, 1990DH

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 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
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 C7H7F+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.91 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)184.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity177.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.907 ± 0.008EQLias and Ausloos, 1978LLK
8.92 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H6F+12.3HEIYeo and Williams, 1970RDSH

De-protonation reactions

C7H6F- + Hydrogen cation = Benzene, 1-fluoro-2-methyl-

By formula: C7H6F- + H+ = C7H7F

Quantity Value Units Method Reference Comment
Δr375.4 ± 3.0kcal/molD-EAKim, Wenthold, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Δr368.3 ± 3.1kcal/molH-TSKim, Wenthold, et al., 1999gas phase; B

References

Go To: Top, Condensed phase thermochemistry data, 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.

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Potter and Saylor, 1951
Potter, John C.; Saylor, John H., The Vapor Pressures and Freezing Points of Some Organic Fluorine Compounds 1,2, J. Am. Chem. Soc., 1951, 73, 1, 90-91, https://doi.org/10.1021/ja01145a032 . [all data]

Mousa, 1984
Mousa, A.H.N., The vapour pressures and saturated vapour volumes of O-fluorotoluene in the temperature range 450--530 K, Journal of Fluorine Chemistry, 1984, 25, 2, 165-168, https://doi.org/10.1016/S0022-1139(00)80946-X . [all data]

Mozhginskay and Kolysko, 1974
Mozhginskay, L.V.; Kolysko, L.E., Zh. Fiz. Khim., 1974, 48, 1506. [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]

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]

Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A., Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine, Thermochim. Acta, 1990, 158, 335-345. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [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]

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]

Kim, Wenthold, et al., 1999
Kim, J.B.; Wenthold, P.G.; Lineberger, W.C., Ultraviolet photoelectron spectroscopy of o-, m-, and p-halobenzyl anions, J. Phys. Chem. A, 1999, 103, 50, 10833-10841, https://doi.org/10.1021/jp992817o . [all data]


Notes

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