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Benzene, 1,3-dimethyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas4.12 ± 0.18kcal/molCcbProsen, Johnson, et al., 1946ALS
Quantity Value Units Method Reference Comment
gas85.60 ± 0.30cal/mol*KN/APitzer K.S., 1943GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
20.84200.Draeger, 1985Discrepancies with other statistically calculated values of S(T) and Cp(T) [ Pitzer K.S., 1943, Taylor W.J., 1946, Hastings S.H., 1957, Chao J., 1984] do not exceed 1.5 J/mol*K.; GT
27.63273.15
30.07 ± 0.1298.15
30.26300.
39.94400.
48.49500.
55.64600.
61.59700.
66.59800.
70.79900.
74.381000.
77.461100.
80.091200.
82.361300.
84.321400.
85.991500.

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
39.10 ± 0.40393.Taylor W.J., 1946Please also see Pitzer K.S., 1943.; GT
42.40 ± 0.40428.
45.40 ± 0.40463.

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-6.08 ± 0.18kcal/molCcbProsen, Johnson, et al., 1946ALS
Quantity Value Units Method Reference Comment
Deltacliquid-1087.37 ± 0.13kcal/molCmCoops, Mulder, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -1086.94 ± 0.13 kcal/mol; Corresponding «DELTA»fliquid = -6.61 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-1087.92 ± 0.15kcal/molCcbProsen, Johnson, et al., 1946Corresponding «DELTA»fliquid = -6.06 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-1091.7kcal/molCcbRichards and Barry, 1915At 291 K; Corresponding «DELTA»fliquid = -2.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-1095.0kcal/molCcbRichards and Jesse, 1910At 293 K; Corresponding «DELTA»fliquid = 1.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid60.660cal/mol*KN/APitzer and Scott, 1943DH
liquid60.30cal/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 66.94 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
44.128298.15Grolier, Roux-Desgranges, et al., 1993DH
43.3915298.15Fortier and Benson, 1979DH
43.3752298.15Fortier and Benson, 1977DH
47.61336.Swietoslawski and Zielenkiewicz, 1958Mean value 21 to 106 C.; DH
44.10298.Kurbatov, 1947T = 16 to 132 C, mean Cp, three temperatures.; DH
43.781298.15Pitzer and Scott, 1943T = 14 to 320 K.; DH
41.90275.3Huffman, Parks, et al., 1930T = 96 to 275 K. Value is unsmoothed experimental datum.; DH
42.59303.Willams and Daniels, 1924T = 303 to 348 K. Equation only.; 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:
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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil412.3 ± 0.3KAVGN/AAverage of 40 out of 43 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus225. ± 4.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple219.6KN/AHuffman, Parks, et al., 1930, 2Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc618. ± 4.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Pc34.9 ± 0.4atmN/ATsonopoulos and Ambrose, 1995 
Pc34.949atmN/AAmbrose, 1987Uncertainty assigned by TRC = 0.05 atm; TRC
Pc34.95atmN/AAmbrose, Broderick, et al., 1967Uncertainty assigned by TRC = 0.06 atm; TRC
Pc33.0000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5000 atm; TRC
Pc34.64atmN/AAltschul, 1893Uncertainty assigned by TRC = 0.0387 atm; TRC
Quantity Value Units Method Reference Comment
Vc0.375l/molN/ATsonopoulos and Ambrose, 1995 
Quantity Value Units Method Reference Comment
rhoc2.67 ± 0.04mol/lN/ATsonopoulos and Ambrose, 1995 
rhoc2.684mol/lN/AAkhundov and Asadullaeva, 1968Uncertainty assigned by TRC = 0.05 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap10. ± 1.kcal/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.523412.3N/AMajer and Svoboda, 1985 
9.37375.N/ASwiatek and Malanowski, 2002Based on data from 360. - 410. K.; AC
9.73342.N/APark and Gmehling, 1989Based on data from 327. - 412. K.; AC
10.7282.AStephenson and Malanowski, 1987Based on data from 267. - 301. K.; AC
8.96427.AStephenson and Malanowski, 1987Based on data from 412. - 462. K.; AC
8.70476.AStephenson and Malanowski, 1987Based on data from 461. - 554. K.; AC
8.65565.AStephenson and Malanowski, 1987Based on data from 550. - 617. K.; AC
9.66346.MMStephenson and Malanowski, 1987Based on data from 331. - 415. K. See also Willingham, Taylor, et al., 1945 and Forziati, Norris, et al., 1949.; AC
9.25395.N/AMachat, 1983Based on data from 380. - 411. K.; AC
10.3288.N/APitzer and Scott, 1943Based on data from 273. - 333. K. See also Boublik, Fried, et al., 1984.; 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
332.4 - 413.194.130361463.218-57.991Williamham, Taylor, et al., 1945Coefficents calculated by NIST from author's data.
273. - 333.5.086281996.545-14.772Pitzer and Scott, 1943Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.7651225.27Pitzer and Scott, 1943DH
2.770225.3Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.28225.27Pitzer and Scott, 1943DH

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.0497166.crystaline, IIcrystaline, IHuffman, Parks, et al., 1930DH
2.7349219.6crystaline, IliquidHuffman, Parks, et al., 1930DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.299166.crystaline, IIcrystaline, IHuffman, Parks, et al., 1930DH
12.45219.6crystaline, IliquidHuffman, Parks, et al., 1930DH

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, 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - 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

C3H9Si+ + Benzene, 1,3-dimethyl- = (C3H9Si+ bullet Benzene, 1,3-dimethyl-)

By formula: C3H9Si+ + C8H10 = (C3H9Si+ bullet C8H10)

Quantity Value Units Method Reference Comment
Deltar29.0kcal/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar35.1cal/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
12.7468.PHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M

C9H12+ + Benzene, 1,3-dimethyl- = (C9H12+ bullet Benzene, 1,3-dimethyl-)

By formula: C9H12+ + C8H10 = (C9H12+ bullet C8H10)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar14.3kcal/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
6.2300.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

C8H9- + Hydrogen cation = Benzene, 1,3-dimethyl-

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar381.0 ± 2.6kcal/molG+TSCaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar373.9 ± 2.5kcal/molIMRECaldwell and Bartmessgas phase; value altered from reference due to change in acidity scale; B

Chlorine anion + Benzene, 1,3-dimethyl- = (Chlorine anion bullet Benzene, 1,3-dimethyl-)

By formula: Cl- + C8H10 = (Cl- bullet C8H10)

Quantity Value Units Method Reference Comment
Deltar3.90kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
4.4300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

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

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR 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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291455

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.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of combustion and formation at 25°C of the alkylbenzenes through C10H14, and of the higher normal monoalkylbenzenes, J. Res. NBS, 1946, 36, 455-461. [all data]

Pitzer K.S., 1943
Pitzer K.S., The thermodynamics and molecular structure of benzene and its methyl derivatives, J. Am. Chem. Soc., 1943, 65, 803-829. [all data]

Draeger, 1985
Draeger, J.A., The methylbenzenes II. Fundamental vibrational shifts, statistical thermodynamic functions, and properties of formation, J. Chem. Thermodyn., 1985, 17, 263-275. [all data]

Taylor W.J., 1946
Taylor W.J., Heats, equilibrium constants, and free energies of formation of the alkylbenzenes, J. Res. Nat. Bur. Stand., 1946, 37, 95-122. [all data]

Hastings S.H., 1957
Hastings S.H., Thermodynamic properties of selected methylbenzenes from 0 to 1000 K, J. Phys. Chem., 1957, 61, 730-735. [all data]

Chao J., 1984
Chao J., Chemical thermodynamic properties of toluene, o-, m- and p-xylenes, Thermochim. Acta, 1984, 72, 323-334. [all data]

Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J., The heats of combustion of a number of hydrocarbons, Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [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]

Richards and Barry, 1915
Richards, T.W.; Barry, F., The heats of combustion of aromatic hydrocarbons and hexamethylene, J. Am. Chem. Soc., 1915, 37, 993-1020. [all data]

Richards and Jesse, 1910
Richards, T.W.; Jesse, R.H., Jr., The heats of combustion of the octanes and xylenes, J. Am. Chem. Soc., 1910, 32, 268-298. [all data]

Pitzer and Scott, 1943
Pitzer, K.S.; Scott, D.W., The thermodynamics and molecular structure of benzene and its methyl derivatives, J. Am. Chem. Soc., 1943, 65, 803-829. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Fortier and Benson, 1979
Fortier, J.-L.; Benson, G.C., Heat capacities of some binary aromatic hydrocarbon mixtures containing benzene or toluene, J. Chem. Eng. Data, 1979, 24(1), 34-37. [all data]

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]

Swietoslawski and Zielenkiewicz, 1958
Swietoslawski, W.; Zielenkiewicz, A., Mean specific heats of binary positive azeotropes, Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1958, 6, 367-369. [all data]

Kurbatov, 1947
Kurbatov, V.Ya., Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons, Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

Huffman, Parks, et al., 1930, 2
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal Data on Organic Compounds: VII The Heat Capacities, Entropies and Free Energies of Twelve Aromatic Hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-58. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Ambrose, 1987
Ambrose, D., Vapor Pressures of Some Aromatic Hydrocarbons, J. Chem. Thermodyn., 1987, 19, 1007. [all data]

Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R., The Vapour Pressures above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons, J. Chem. Soc. , 1967, 1967, 1967, 633-41. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Altschul, 1893
Altschul, M., The critical values of some organic compounds, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]

Akhundov and Asadullaeva, 1968
Akhundov, T.S.; Asadullaeva, N.N., Specific volumes of m-xylene near the critical point, Izv. Vyssh. Uchebn. Zaved., Neft Gaz, 1968, 11, 6, 836. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Swiatek and Malanowski, 2002
Swiatek, Barbara E.; Malanowski, Stanislaw K., Vapor-Liquid Equilibrium in m -Xylene + Cyclohexanol at 19.99 and 94.93 kPa, J. Chem. Eng. Data, 2002, 47, 3, 478-481, https://doi.org/10.1021/je010246z . [all data]

Park and Gmehling, 1989
Park, So Jin; Gmehling, Juergen, Isobaric vapor-liquid equilibrium data for the binary systems 1,3,5-trimethylbenzene/N-formylmorpholine and m-xylene/N-formylmorpholine, J. Chem. Eng. Data, 1989, 34, 4, 399-401, https://doi.org/10.1021/je00058a008 . [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]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D., Vapor pressures and boiling points of sixty API-NBS hydrocarbons, J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050 . [all data]

Machat, 1983
Machat, V., , Thesis, Utzcht, Prague, 1983. [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]

Williamham, Taylor, et al., 1945
Williamham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [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]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [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]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References