Benzene, 1-fluoro-3-nitro-

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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-706.35kcal/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 by: Robert L. Brown and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil478.2KN/AAldrich Chemical Company Inc., 1990 
Tboil473. - 474.KN/APCR Inc., 1990 

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference
359.20.025Weast and Grasselli, 1989

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 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. 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

Bromine anion + Benzene, 1-fluoro-3-nitro- = (Bromine anion • Benzene, 1-fluoro-3-nitro-)

By formula: Br- + C6H4FNO2 = (Br- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr17.3 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Δr22.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr7.9 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
7.9423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Chlorine anion + Benzene, 1-fluoro-3-nitro- = (Chlorine anion • Benzene, 1-fluoro-3-nitro-)

By formula: Cl- + C6H4FNO2 = (Cl- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr18.7 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr21.2cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr12.3 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

F6S- + Benzene, 1-fluoro-3-nitro- = (F6S- • Benzene, 1-fluoro-3-nitro-)

By formula: F6S- + C6H4FNO2 = (F6S- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr15.7 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr7.9 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

F6S- + Benzene, 1-fluoro-3-nitro- = (F6S- • Benzene, 1-fluoro-3-nitro-)

By formula: F6S- + C6H4FNO2 = (F6S- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr15.7kcal/molPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr26.1cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

EA (eV) Method Reference Comment
1.24 ± 0.10TDEqChowdhury, Heinis, et al., 1986ΔGea(423 K) = -27.7 kcal/mol, ΔS = -2 eu; B
1.206 ± 0.087IMREHuh, Kang, et al., 1999ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B
<1.240 ± 0.050PDMock and Grimsrud, 1989B
1.210 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -27.2 kcal/mol; ΔSea =-2.0, est. from data in Chowdhury, Heinis, et al., 1986; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.88PEPalmer, Moyes, et al., 1979LLK
9.9 ± 0.1EIBrown, 1970RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4F+12.2 ± 0.1NO2EIBrown, 1970RDSH
C6H4OF+10.3 ± 0.1NOEIBrown, 1970RDSH

Ion clustering 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
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

Bromine anion + Benzene, 1-fluoro-3-nitro- = (Bromine anion • Benzene, 1-fluoro-3-nitro-)

By formula: Br- + C6H4FNO2 = (Br- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr17.3 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Δr22.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr7.9 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
7.9423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Chlorine anion + Benzene, 1-fluoro-3-nitro- = (Chlorine anion • Benzene, 1-fluoro-3-nitro-)

By formula: Cl- + C6H4FNO2 = (Cl- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr18.7 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr21.2cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr12.3 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

F6S- + Benzene, 1-fluoro-3-nitro- = (F6S- • Benzene, 1-fluoro-3-nitro-)

By formula: F6S- + C6H4FNO2 = (F6S- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr15.7 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr7.9 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

F6S- + Benzene, 1-fluoro-3-nitro- = (F6S- • Benzene, 1-fluoro-3-nitro-)

By formula: F6S- + C6H4FNO2 = (F6S- • C6H4FNO2)

Quantity Value Units Method Reference Comment
Δr15.7kcal/molPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr26.1cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M

Mass spectrum (electron ionization)

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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

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- 999
NIST MS number 230444

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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.

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

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Role of Binding Energies in A-.B and A.B- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A- + B = A + B- Involving Perfluoro Compounds: SF6, C6F11CF3, J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687 . [all data]

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P., Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure, J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for nitrobenzene, the nitrotoluenes, dinitrobenzenes and fluoronitrobenzenes, J. Mol. Struct., 1979, 55, 243. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry. IX. Competing [M-NO2] and [M-NO] reactions in substituted nitrobenzenes. Approximate activation energies from ionization and appearance potentials, Org. Mass Spectrom., 1970, 4, 533. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References