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Benzene, chloro-

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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, Ion clustering 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
Deltafgas13.01kcal/molCcrPlatonov and Simulin, 1985 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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 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
Deltafliquid2.74 ± 0.25kcal/molCcrKolesov, Tomareva, et al., 1967Reanalyzed by Cox and Pilcher, 1970, Original value = 2.82 kcal/mol; ALS
Deltafliquid2.55 ± 0.19kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
Deltacliquid-743.9 ± 0.2kcal/molCcrPlatonov and Simulin, 1985ALS
Deltacliquid-743.48 ± 0.24kcal/molCcrKolesov, Tomareva, et al., 1967ALS
Deltacliquid-743.04 ± 0.19kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Deltacliquid-743.7 ± 2.0kcal/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -742.64 kcal/mol; ALS
Quantity Value Units Method Reference Comment
liquid47.20cal/mol*KN/AStull, 1937Extrapolation below 91 K, 44.02 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
36.35298.15Shehatta, 1993DH
36.754298.15Perez-Casas, Aicart, et al., 1988DH
35.99303.15Reddy, 1986T = 303.15, 313.15 K.; DH
36.0390298.15Fortier and Benson, 1977DH
35.30298.Deshpande and Bhatagadde, 1971T = 298 to 318 K.; DH
37.60305.6Phillip, 1939DH
35.870298.1Stull, 1937T = 90 to 320 K.; DH
34.80293.2Williams and Daniels, 1925T = 20 to 80°C.; DH
33.70298.von Reis, 1881T = 294 to 425 K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
25.41216.8Andrews and Haworth, 1928T = 101 to 217 K. Value is unsmoothed experimental datum.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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
Tboil404.9 ± 0.6KAVGN/AAverage of 53 out of 55 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus228.0 ± 0.4KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple227.9KN/AStull, 1937, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc632.35KN/AYoung, 1910Uncertainty assigned by TRC = 0.3 K; disappearance of meniscus; TRC
Tc632.65KN/ALivingston, Morgan, et al., 1908Uncertainty assigned by TRC = 6. K; calculation based on extrap. of density and surface tension; TRC
Tc635.35KN/AAltschul, 1893Uncertainty assigned by TRC = 2. K; disappearance of meniscus; TRC
Quantity Value Units Method Reference Comment
Pc44.600atmN/AYoung, 1910Uncertainty assigned by TRC = 0.2999 atm; TRC
Quantity Value Units Method Reference Comment
rhoc3.24mol/lN/AYoung, 1910Uncertainty assigned by TRC = 0.04 mol/l; law of rectilinear diam.; TRC
Quantity Value Units Method Reference Comment
Deltavap9.7 ± 0.9kcal/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.411404.9N/AMajer and Svoboda, 1985 
11.5258. - 313.GCLiu and Dickhut, 1994AC
8.46420.AStephenson and Malanowski, 1987Based on data from 405. - 597. K.; AC
9.27348.AStephenson and Malanowski, 1987Based on data from 333. - 405. K. See also Brown, 1952 and Boublik, Fried, et al., 1984.; AC
8.91278.MEZibberman-Granovskaya, 1940Based on data from 253. - 303. 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
335.19 - 404.884.105121435.675-55.124Brown, 1952, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.28227.9Domalski and Hearing, 1996AC
2.284227.89Stull, 1937DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
10.02227.89Stull, 1937DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Chlorine anion + Benzene, chloro- = (Chlorine anion bullet Benzene, chloro-)

By formula: Cl- + C6H5Cl = (Cl- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar12.00 ± 0.10kcal/molTDAsSieck, 1985gas phase; B,M
Deltar13.6 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar12.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Deltar16.5cal/mol*KPHPMSSieck, 1985gas phase; M
Deltar22.4cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar7.10 ± 0.20kcal/molTDAsSieck, 1985gas phase; B
Deltar6.9 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar6.50kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.6300.PHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
6.5300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar391.0 ± 1.9kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar382.8 ± 2.0kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar394.4 ± 1.3kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar386.6 ± 1.4kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar386.7 ± 2.1kcal/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar388.2 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar387.7 ± 3.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Quantity Value Units Method Reference Comment
Deltar378.5 ± 2.0kcal/molIMREAndrade and Riveros, 1996gas phase; B
Deltar380.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar379.5 ± 3.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Deltar379.0 ± 5.0kcal/molIMRBBartmess and McIver Jr., 1979gas phase; Between H2O, MeOH; B

Bromine anion + Benzene, chloro- = (Bromine anion bullet Benzene, chloro-)

By formula: Br- + C6H5Cl = (Br- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar11.1 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar2.6 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.6423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H7N+ + Benzene, chloro- = (C6H7N+ bullet Benzene, chloro-)

By formula: C6H7N+ + C6H5Cl = (C6H7N+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
4.0297.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C9H12+ + Benzene, chloro- = (C9H12+ bullet Benzene, chloro-)

By formula: C9H12+ + C6H5Cl = (C9H12+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.4kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.9300.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Nitric oxide anion + Benzene, chloro- = (Nitric oxide anion bullet Benzene, chloro-)

By formula: NO- + C6H5Cl = (NO- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar38.5kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Benzene, chloro- + 1-Chloro-2,4-diisopropylbenzene = Benzene, 1-chloro-2-(1-methylethyl)- + Benzene, 1-chloro-4-(1-methylethyl)-

By formula: C6H5Cl + C12H17Cl = C9H11Cl + C9H11Cl

Quantity Value Units Method Reference Comment
Deltar-0.20 ± 0.10kcal/molEqkNesterova, Rozhnov, et al., 1985liquid phase; ALS

Benzene, chloro- + 2,4-Di-t-butyl chlorobenzene = 1-Chloro-4-(1,1-dimethylethyl)benzene + Benzene, 1-tert-butyl-2-chloro-

By formula: C6H5Cl + C14H21Cl = C10H13Cl + C10H13Cl

Quantity Value Units Method Reference Comment
Deltar-0.06 ± 0.17kcal/molEqkKovzel, Nesterova, et al., 1981liquid phase; ALS

Benzene, 1-chloro-2-(1-methylethyl)- + Benzene = Benzene, chloro- + Benzene, (1-methylethyl)-

By formula: C9H11Cl + C6H6 = C6H5Cl + C9H12

Quantity Value Units Method Reference Comment
Deltar-0.14 ± 0.10kcal/molEqkNesterova, Rozhnov, et al., 1985liquid phase; ALS

Benzene, chloro- + Benzene, 1-chloro-3,5-bis(1,1-dimethylethyl)- = 2m-Tert-butyl chlorobenzene

By formula: C6H5Cl + C14H21Cl = 2C10H13Cl

Quantity Value Units Method Reference Comment
Deltar0. ± 0.02kcal/molEqkKovzel, Nesterova, et al., 1981liquid phase; ALS

Benzene + Chlorine = Benzene, chloro- + Hydrogen chloride

By formula: C6H6 + Cl2 = C6H5Cl + HCl

Quantity Value Units Method Reference Comment
Deltar-32.0kcal/molCmKirkbride, 1956liquid phase; ALS

Henry's Law data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: 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 Comment
0.273800.LN/A 
0.26 MN/A 
0.321900.XN/A 
0.22 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.244700.XN/A 
0.262700.XN/A 
0.252100.XN/A 
0.303500.XLeighton and Calo, 1981 
0.29 LN/A 
0.32 MN/A 
0.294200.XN/A 
0.27 MMackay, Shiu, et al., 1979 
0.27 TMackay, Shiu, et al., 1979 
0.22 VN/A 
0.294600.MN/A 

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Ion clustering 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 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

View reactions leading to C6H5Cl+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.07 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)180.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity173.2kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.08PEFujisawa, Ohno, et al., 1986LBLHLM
8.8PEKlasinc, Kovac, et al., 1983LBLHLM
9.07 ± 0.03PERuscic, Klasinc, et al., 1981LLK
9.10PEKimura, Katsumata, et al., 1981LLK
9.10 ± 0.02PEMohraz, Maier, et al., 1980LLK
9.10 ± 0.02PEMaier and Marthaler, 1978LLK
9.059 ± 0.008EQLias and Ausloos, 1978LLK
9.09PEBehan, Johnstone, et al., 1976LLK
9.55EIBaldwin, Loudon, et al., 1976LLK
9.07 ± 0.02PIPECOBaer, Tsai, et al., 1976LLK
9.1 ± 0.1EIGilbert, Leach, et al., 1973LLK
8.99EICooks, Bertrand, et al., 1973LLK
9.08 ± 0.01PISergeev, Akopyan, et al., 1970RDSH
9.035PIMomigny, Goffart, et al., 1968RDSH
9.05SQuemerais, Morlais, et al., 1967RDSH
9.07PIBralsford, Harris, et al., 1960RDSH
9.07 ± 0.02PIWatanabe, 1957RDSH
9.07PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.067PEPotts, Lyus, et al., 1980Vertical value; LLK
9.08PESell and Kupperman, 1978Vertical value; LLK
9.07PEKlasinc, Novak, et al., 1978Vertical value; LLK
9.09PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H4+17.6 ± 0.1?EIMomigny, 1959RDSH
C6H4+14.9 ± 0.2HClEIMomigny, 1959RDSH
C6H5+11.81ClDERRipoche, Dimicoli, et al., 1991LL
C6H5+12.88 ± 0.05ClEIBurgers and Holmes, 1984LBLHLM
C6H5+13.1 ± 0.1ClEIBurgers and Holmes, 1984LBLHLM
C6H5+12.25 ± 0.04ClPIPECORosenstock, Stockbauer, et al., 1980LLK
C6H5+12.47 ± 0.06ClPIRosenstock, Stockbauer, et al., 1979LLK
C6H5+13.06ClPIPECOBaer, Tsai, et al., 1976LLK
C6H5+12.81ClEIJohnstone and Mellon, 1972LLK
C6H5+12.55 ± 0.07ClPISergeev, Akopyan, et al., 1970RDSH
C6H5+13.2 ± 0.1ClEIMajer and Patrick, 1962RDSH

De-protonation reactions

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar391.0 ± 1.9kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar390.2 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar382.8 ± 2.0kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar394.4 ± 1.3kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar389.7 ± 2.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Deltar386.6 ± 1.4kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Deltar382.0 ± 2.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Deltar386.7 ± 2.1kcal/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar388.2 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; B
Deltar387.7 ± 3.1kcal/molG+TSWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Quantity Value Units Method Reference Comment
Deltar378.5 ± 2.0kcal/molIMREAndrade and Riveros, 1996gas phase; B
Deltar380.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; B
Deltar379.5 ± 3.0kcal/molIMRBWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Deltar379.0 ± 5.0kcal/molIMRBBartmess and McIver Jr., 1979gas phase; Between H2O, MeOH; B

Ion clustering data

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, 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
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, chloro- = (Bromine anion bullet Benzene, chloro-)

By formula: Br- + C6H5Cl = (Br- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar11.1 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar2.6 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.6423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H7N+ + Benzene, chloro- = (C6H7N+ bullet Benzene, chloro-)

By formula: C6H7N+ + C6H5Cl = (C6H7N+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
4.0297.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

C9H12+ + Benzene, chloro- = (C9H12+ bullet Benzene, chloro-)

By formula: C9H12+ + C6H5Cl = (C9H12+ bullet C6H5Cl)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar11.4kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.9300.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Chlorine anion + Benzene, chloro- = (Chlorine anion bullet Benzene, chloro-)

By formula: Cl- + C6H5Cl = (Cl- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar12.00 ± 0.10kcal/molTDAsSieck, 1985gas phase; B,M
Deltar13.6 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar12.6kcal/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Deltar16.5cal/mol*KPHPMSSieck, 1985gas phase; M
Deltar22.4cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar7.10 ± 0.20kcal/molTDAsSieck, 1985gas phase; B
Deltar6.9 ± 1.0kcal/molIMRELarson and McMahon, 1984gas phase; B,B,M
Deltar6.50kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.6300.PHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
6.5300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Nitric oxide anion + Benzene, chloro- = (Nitric oxide anion bullet Benzene, chloro-)

By formula: NO- + C6H5Cl = (NO- bullet C6H5Cl)

Quantity Value Units Method Reference Comment
Deltar38.5kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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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: 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.
NIST MS number 1680

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, Ion clustering 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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Source Grammaticakis, 1949
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. 78
Instrument n.i.g.
Melting point -45.2
Boiling point 131.7

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, Ion clustering 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.

Platonov and Simulin, 1985
Platonov, V.A.; Simulin, Yu.N., Determination of the standard enthalpies of formation of polychlorobenzenes. III. The standard enthalpies of formation of mono-1,2,4- and 1,3,5-tri-, and 1,2,3,4- and 1,2,3,5-tetrachlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1985, 59, 179-181. [all data]

Kolesov, Tomareva, et al., 1967
Kolesov, V.P.; Tomareva, E.M.; Skuratov, S.M.; Alekhin, S.P., Calorimeter having a rotating bomb for determining heats of combustion of chlorinated organic compounds, Russ. J. Phys. Chem. (Engl. Transl.), 1967, 41, 817-820. [all data]

Cox and Pilcher, 1970
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Hubbard, Knowlton, et al., 1954
Hubbard, W.N.; Knowlton, J.W.; Huffman, H.M., Combustion calorimetry of organic chlorine compounds. Heats of combustion of chlorobenzene, the dichlorobenzenes and o- and p-chloroethylbenzene, J. Phys. Chem., 1954, 58, 396. [all data]

Smith, Bjellerup, et al., 1953
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Stull, 1937
Stull, D.R., A semi-micro calorimeter for measuring heat capacities at low temperatures, J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]

Shehatta, 1993
Shehatta, I., Heat capacity at constant pressure of some halogen compounds, Thermochim. Acta, 1993, 213, 1-10. [all data]

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Perez-Casas, S.; Aicart, E.; Trojo, L.M.; Costas, M., Excess heat capacity. Chlorobenzene-2,2,4,4,6,8,8-heptamethylnonane, Int. Data Ser., Sel. Data Mixtures, 1988, (2)A, 123. [all data]

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Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

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Stull, 1937, 2
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

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Liu and Dickhut, 1994
Liu, Kewen; Dickhut, Rebecca M., Saturation vapor pressures and thermodynamic properties of benzene and selected chlorinated benzenes at environmental temperatures, Chemosphere, 1994, 29, 3, 581-589, https://doi.org/10.1016/0045-6535(94)90445-6 . [all data]

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Brown, 1952
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Boublik, Fried, et al., 1984
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Zibberman-Granovskaya, 1940
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Brown, 1952, 2
Brown, I., Liquid-Vapour Equilibria. III. The Systems Benzene-n-Heptane, n-Hexane-Chlorobenzene, and cycloHexane-Nitrobenzene, Aust. J. Sci. Res. Ser. A:, 1952, 5, 530-540. [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]

Sieck, 1985
Sieck, L.W., Thermochemistry of Solvation of NO2- and C6H5NO2- by Polar Molecules in the Vapor Phase. Comparison with Cl- and Variation with Ligand Structure., J. Phys. Chem., 1985, 89, 25, 5552, https://doi.org/10.1021/j100271a049 . [all data]

Larson and McMahon, 1984
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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]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [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]

Wenthold and Squires, 1994
Wenthold, P.G.; Squires, R.R., Gas-phase properties and reactivity of the acetate radical anion. Determination of the C-H bond strengths in acetic acid and acetate ion, J. Am. Chem. Soc., 1994, 116, 26, 11890, https://doi.org/10.1021/ja00105a032 . [all data]

Wenthold, Paulino, et al., 1991
Wenthold, P.G.; Paulino, J.A.; Squires, R.R., The Absolute Heats of Formation of ortho-Benzyne, meta-Benzyne, and para-Benzyne, J. Am. Chem. Soc., 1991, 113, 19, 7414, https://doi.org/10.1021/ja00019a044 . [all data]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H., Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies, J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N., Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements, J. Chem. Thermodyn., 1985, 17, 649-656. [all data]

Kovzel, Nesterova, et al., 1981
Kovzel, E.N.; Nesterova, T.N.; Rozhnov, A.M.; Kartavtseva, T.A., Study of equilibrium in in the chlorobenzene-butylchlorobenzenes systems, Termodin. Organ. Soedin., 1981, 65-68. [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]

Leighton and Calo, 1981
Leighton, D.T.; Calo, J.M., Distribution Coefficients of Chlorinated Hydrocarbons in Dilute Air-Water Systems for Groundwater Contamination Applications, J. Chem. Eng. Data, 1981, 26, 382-385. [all data]

Mackay, Shiu, et al., 1979
Mackay, D.; Shiu, W.-Y.; Sutherland, R.P., Determination of Air-Water Henry's Law Constants for Hydrophobic Pollutants, Environ. Sci. Technol., 1979, 13, 333-337. [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]

Fujisawa, Ohno, et al., 1986
Fujisawa, S.; Ohno, K.; Masuda, S.; Harada, Y., Penning ionization electron spectroscopy of monohalogenobenzenes: C6H5F, C6H5Cl, C6H5Br, and C6H5I, J. Am. Chem. Soc., 1986, 108, 6505. [all data]

Klasinc, Kovac, et al., 1983
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Ruscic, Klasinc, et al., 1981
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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]

Mohraz, Maier, et al., 1980
Mohraz, M.; Maier, J.P.; Heilbronner, E., He(I «alpha») and He(I«alpha») photoelectron spectra of fluorinated chloro- and bromobenzenes, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 429. [all data]

Maier and Marthaler, 1978
Maier, J.P.; Marthaler, O., Emission spectra of the radical cations of 1,3-dichlorobenzene, 1,4-dichlorobenzene and 1,3,5-trichlorobenzene in the gas phase, Chem. Phys., 1978, 32, 419. [all data]

Lias and Ausloos, 1978
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Grammaticakis, 1949
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'ultraviolet moyen des anilines orthosubstituees. II. Ortho-halogenanilines N-substituees, Bull. Soc. Chim. Fr., 1949, 16, 761. [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, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References