Aniline

• Formula: C₆H₇N
• Molecular weight: 93.1265
• IUPAC Standard InChI: InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 Copy

  
• IUPAC Standard InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 62-53-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Isotopologues:
  • Benzen-d5-amine
• Other names: Benzenamine; Aminobenzene; Aminophen; Anyvim; Benzene, amino-; Blue Oil; C.I. 76000; Phenylamine; Aniline Oil; Aniline reagent; Anilin; Anilina; Benzidam; C.I. Oxidation base 1; Cyanol; Huile D'aniline; Krystallin; Kyanol; NCI-C03736; Rcra waste number U012; UN 1547; Benzeneamine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, 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
DRB - Donald R. Burgess, Jr.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, 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

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Ion clustering data, Gas Chromatography, 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

 +  = ( • )

By formula: Br^- + C₆H₇N = (Br^- • C₆H₇N)

Free energy of reaction

C₆H₆N^- +  =

By formula: C₆H₆N^- + H⁺ = C₆H₇N

C₉H₁₃N⁺ +  = (C₉H₁₃N⁺ • )

By formula: C₉H₁₃N⁺ + C₆H₇N = (C₉H₁₃N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₇H₉N⁺ +  = (C₇H₉N⁺ • )

By formula: C₇H₉N⁺ + C₆H₇N = (C₇H₉N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₈H₁₁N⁺ +  = (C₈H₁₁N⁺ • )

By formula: C₈H₁₁N⁺ + C₆H₇N = (C₈H₁₁N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: F^- + C₆H₇N = (F^- • C₆H₇N)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₇N = (C₆H₇N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

 +  =

By formula: C₆H₇N + C₈H₄O₃ = C₁₄H₁₁NO₃

= 0.5 + 0.5

By formula: C₇H₉N = 0.5C₈H₁₁N + 0.5C₆H₇N

 +  = ( • )

By formula: K⁺ + C₆H₇N = (K⁺ • C₆H₇N)

 +  =  + 

By formula: C₇H₅IO + C₆H₇N = HI + C₁₃H₁₁NO

 +  =  + 

By formula: C₇H₅BrO + C₆H₇N = HBr + C₁₃H₁₁NO

 +  =  + 

By formula: C₆H₇N + C₇H₅ClO = HCl + C₁₃H₁₁NO

 +  =  + 

By formula: C₈H₉NO + H₂O = C₆H₇N + C₂H₄O₂

 +  =

By formula: C₇H₄N₂O₃ + C₆H₇N = C₁₃H₁₁N₃O₃

 +  =

By formula: C₇H₁₁NO + C₆H₇N = C₁₃H₁₈N₂O

=  + 

By formula: C₁₅H₁₇NO₂ = C₉H₁₀O₂ + C₆H₇N

 +  =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

=  + 

By formula: C₁₃H₁₂N₂O = C₇H₅NO + C₆H₇N

 +  = ( • )

By formula: I^- + C₆H₇N = (I^- • C₆H₇N)

 +  =  + 

By formula: C₄H₅N₃O + C₆H₇N = C₈H₉NO + C₂H₃N₃

 +  =  + 

By formula: C₃H₄N₄O + C₆H₇N = C₈H₉NO + CH₂N₄

 +  =  + 

By formula: C₄H₆O₃ + C₆H₇N = C₈H₉NO + C₂H₄O₂

 +  =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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

 +  = ( • )

By formula: Br^- + C₆H₇N = (Br^- • C₆H₇N)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₇N = (C₆H₇N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₇H₉N⁺ +  = (C₇H₉N⁺ • )

By formula: C₇H₉N⁺ + C₆H₇N = (C₇H₉N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₈H₁₁N⁺ +  = (C₈H₁₁N⁺ • )

By formula: C₈H₁₁N⁺ + C₆H₇N = (C₈H₁₁N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

C₉H₁₃N⁺ +  = (C₉H₁₃N⁺ • )

By formula: C₉H₁₃N⁺ + C₆H₇N = (C₉H₁₃N⁺ • C₆H₇N)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

 +  = ( • )

By formula: F^- + C₆H₇N = (F^- • C₆H₇N)

 +  = ( • )

By formula: I^- + C₆H₇N = (I^- • C₆H₇N)

 +  = ( • )

By formula: K⁺ + C₆H₇N = (K⁺ • C₆H₇N)

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Normal alkane RI, non-polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Normal alkane RI, polar column, custom temperature program

View large format table.

Lee's RI, non-polar column, temperature ramp

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, Notes

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

Hatton, Hildenbrand, et al., 1962
Hatton, W.E.; Hildenbrand, D.L.; Sinke, G.C.; Stull, D.R., Chemical thermodynamic properties of aniline, J. Chem. Eng. Data, 1962, 7, 229-231. [all data]

Vriens and Hill, 1952
Vriens, G.N.; Hill, A.G., Equilibria of several reactions of aromatic amines, Ind. Eng. Chem., 1952, 44, 2732-27. [all data]

Cole and Gilbert, 1951
Cole, L.G.; Gilbert, E.C., The heats of combustion of some nitrogen compounds and the apparent energy of the N-N bond, J. Am. Chem. Soc., 1951, 73, 5423-5427. [all data]

Anderson and Gilbert, 1942
Anderson, C.M.; Gilbert, E.C., The apparent energy of the N-N bond as calculated from heats of combustion, J. Am. Chem. Soc., 1942, 64, 2369-2372. [all data]

Lemoult, 1907
Lemoult, M.P., Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques, Ann. Chim. Phys., 1907, 12, 395-432. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Willis, 1947
Willis, J.B., The heats of combustion of some organic bases and their salts. The resonance energies of acridine and phenazine, Trans. Faraday Soc., 1947, 43, 97-102. [all data]

Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A., Capacites calorifiques de durcisseurs amines et resines epoxydes, Thermochim. Acta, 1987, 109, 317-329. [all data]

Nichols and Wads, 1975
Nichols, N.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution, J. Chem. Thermodynam., 1975, 7, 329-336. [all data]

Deshpande and Bhatagadde, 1971
Deshpande, D.D.; Bhatagadde, L.G., Heat capacities at constant volume, free volumes, and rotational freedom in some liquids, Aust. J. Chem., 1971, 24, 1817-1822. [all data]

Crtzen, Jost, et al., 1957
Crtzen, J.L.; Jost, W.; Sieg, L., Gleichgewichtsmessungen im System Anilin-N-Methylanilin, N-N-Dimethylanilin, 1,2-Äthandiol, Z. Elektrochem., 1957, 61, 230-246. [all data]

Hough, Mason, et al., 1950
Hough, E.W.; Mason, D.M.; Sage, B.H., Heat capacities of several organic liquids, J. Am. Chem. Soc., 1950, 72, 5775-5777. [all data]

Ziegler and Andrews, 1942
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482-2485. [all data]

Radulescu and Jula, 1934
Radulescu, D.; Jula, O., Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen, Z. Phys. Chem., 1934, B26, 390-393. [all data]

Ferguson and Miller, 1933
Ferguson, A.; Miller, J.T., A method for the determination of the specific heats of liquids, and a determination of the specific heats of aniline and benzene over the approximate range 20°C to 50°C, Proc. Phys. Soc. London, 1933, 45, 194-207. [all data]

Lang, 1928
Lang, H.R., On the measurement of the variation of the specific heat of aniline with temperature, using the continuous flow electric method, Proc. Roy. Soc. (London), 1928, A118, 138-156. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Hatton, Hildenbrand, et al., 1962, 2
Hatton, W.E.; Hildenbrand, D.L.; Sinke, G.C.; Stull, D.R., Chemical Thermodynamic Properties of Aniline, J. Chem. Eng. Data, 1962, 7, 229. [all data]

Ziegler and Andrews, 1942, 2
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482. [all data]

Parks, Huffman, et al., 1933, 2
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen, J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016 . [all data]

Lagutkin and Kuropatkin, 1981
Lagutkin, O.D.; Kuropatkin, E.I., Critical coefficient of compressibility and critical dens. of aniline, Zh. Fiz. Khim., 1981, 55, 1329. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line: Measurements for Benzenamine, Butylbenzene, sec -Butylbenzene, tert -Butylbenzene, 2,2-Dimethylbutanoic Acid, Tridecafluoroheptanoic Acid, 2-Butyl-2-ethyl-1,3-propanediol, 2,2,4-Trimethyl-1,3-pentanediol, and 1-Chloro-2-propanol, J. Chem. Eng. Data, 2002, 47, 4, 648-666, https://doi.org/10.1021/je010083e . [all data]

Lee, Chen, et al., 1992
Lee, Chang Ha; Chen, Quen; Mohamed, Rahoma S.; Holder, Gerald D., Vapor-liquid equilibria in the system of toluene/aniline, aniline/naphthalene, and naphthalene/quinoline, J. Chem. Eng. Data, 1992, 37, 2, 179-183, https://doi.org/10.1021/je00006a011 . [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]

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]

Maher and Smith, 1979
Maher, Patrick J.; Smith, Buford D., A new total pressure vapor-liquid equilibrium apparatus. The ethanol + aniline system at 313.15, 350.81, and 386.67 K, J. Chem. Eng. Data, 1979, 24, 1, 16-22, https://doi.org/10.1021/je60080a022 . [all data]

Ravdel and Danilov, 1968
Ravdel, A.A.; Danilov, V.V., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1968, 11, 6, 642. [all data]

Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G., Proton relaxation in solid aniline and some methyl derivatives, J. Chem. Soc., Faraday Trans. 2, 1972, 68, 2017, https://doi.org/10.1039/f29726802017 . [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]

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]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Ichino, T.; Stanton, J.F.; Lineberger, W.C., Photoelectron Spectroscopy of Anilinide and Acidity of Aniline, J. Phys. Chem. A, 2012, 116, 12, 3118-3123, https://doi.org/10.1021/jp211463r . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [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]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Kalnin'sh, 1988
Kalnin'sh, K.K., Autocatalysis and effects of the solvent in the reaction of phthalic anhydride with aniline derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1768-1773. [all data]

Pravednikov, Kardash, et al., 1973
Pravednikov, A.N.; Kardash, I.Ye.; Glukhoyedov, N.P.; Ardashnikov, A.Ya., Some features of the synthesis of heat-resistant heterocyclic polymers, Polym. Sci. USSR, 1973, 15, 399-410. [all data]

Matvienko, Kachurin, et al., 1982
Matvienko, N.M.; Kachurin, O.I.; Chekhuta, V.G., Kinetics and equilibrium of the transalkylation reaction of N-methylarylamines, Russ. Chem. Rev., 1982, 48, 42-45. [all data]

Kachurin, Matvienko, et al., 1979
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G., Disproportionation of N-methylaniline, Russ. Chem. Rev., 1979, 45, 43-47. [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [all data]

Kiselev, Khuzyasheva, et al., 1979
Kiselev, V.D.; Khuzyasheva, d.G.; Konovalov, A.I., Thermochemical study of the acylation of para-substituted anilines, J. Gen. Chem. USSR, 1979, 49, 2273-2276. [all data]

Wadso, 1965
Wadso, I., Thermochemical properties of diacetimide, N-butyldiacetimide and N-phenyldiacetimide, Acta Chem. Scand., 1965, 19, 1079-1087. [all data]

Kiselev, Malkov, et al., 1989
Kiselev, V.D.; Malkov, V.B.; Murzin, D.G.; Shakirov, I.M.; Konovalov, A.I., Thermochemical study of the reaction of isocyanate with amines, Dokl. Phys. Chem. (Engl. Transl.), 1989, 308, 711-713, In original 111. [all data]

Kuznetsova, Rakova, et al., 1975
Kuznetsova, V.P.; Rakova, G.V.; Miroshnichenko, E.A.; Lebedev, Yu.A.; Enikolopyan, N.S., Thermochemical study of the interaction of epoxy compounds with primary amines, Dokl. Phys. Chem. (Engl. Transl.), 1975, 225, 1231-1234. [all data]

Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D., Thermal decomposition of substituted ureas, J. Gen. Chem. USSR, 1984, 54, 1317-1320. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Wadso, 1962
Wadso, I., Heats of aminolysis and hydrolysis of some N-acetyl compounds and of acetic anhydride, Acta Chem. Scand., 1962, 16, 471-478. [all data]

Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W., Kinetics of isocyanate amine reactions, J. Appl. Polym. Sci., 1987, 34, 2409-2432. [all data]

Cha and Lee, 1994
Cha, K.-W.; Lee, D.-J., Prediction of retention indices of various compounds in gas-liquid chromatography, J. Korean Chem. Soc., 1994, 38, 2, 108-120, retrieved from http://journal.kcsnet.or.kr/publi/dh/dh94n2/108.pdf. [all data]

Zhang, Li, et al., 1992
Zhang, M.J.; Li, S.D.; Chen, B.J., Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions, Chromatographia, 1992, 33, 3/4, 138-146, https://doi.org/10.1007/BF02275894 . [all data]

Dutoit, 1991
Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [all data]

Dolecka, Raczynska, et al., 1988
Dolecka, E.; Raczynska, E.D.; Drapala, T., Retention indices and basicity of N¹N¹-dimethyl-N²-phenylformamidines ortho-substituent effect, J. Chem. Soc. Perkin Trans. 2:, 1988, 3, 257-260, https://doi.org/10.1039/p29880000257 . [all data]

Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M., Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column, J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6 . [all data]

Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E., Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column, J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7 . [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. II. Fluorinated compounds containing a functional group, J. Chromatogr., 1975, 114, 1, 87-93, https://doi.org/10.1016/S0021-9673(00)85245-0 . [all data]

Ellis and Still, 1979
Ellis, T.S.; Still, R.H., Thermal degradation of polymers. XXI. Vacuum pyrolysis of poly(m-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid at room temperature, J. Appl. Polym. Sci., 1979, 23, 10, 2837-2854, https://doi.org/10.1002/app.1979.070231002 . [all data]

Ellis and Still, 1979, 2
Ellis, T.S.; Still, R.H., Thermal degradation of polymers. XXIII. Vacuum pyrolysis of poly(p-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid or gaseous at room temperature, J. Appl. Polym. Sci., 1979, 23, 10, 2871-2880, https://doi.org/10.1002/app.1979.070231004 . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Still, Evans, et al., 1972
Still, R.H.; Evans, M.B.; Whitehead, A., Thermal Degradation of Polymers. V. Vacuum Pyrolysis of Poly (p-N,N-dimethylaminostyrene) . The Products Volatile at Pyrolysis Temperature, Liquid or Gaseous at Room Temperature, J. Appl. Polym. Sci., 1972, 16, 12, 3207-3221, https://doi.org/10.1002/app.1972.070161213 . [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Li, Wang, et al., 1998
Li, W.; Wang, H.; Sun, Y.; Huang, A.; Sun, Y., Capillary gas chromatographic analysis of volatile components in goat feces, Fenxi Huaxue, 1998, 26, 8, 935-939. [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Maltby, D., Prediction of retention indexes. III. Silylated derivatives of polar compounds, J. Chromatogr., 1991, 586, 1, 113-129, https://doi.org/10.1016/0021-9673(91)80029-G . [all data]

Tello, Lebron-Aguilar, et al., 2009
Tello, A.M.; Lebron-Aguilar, R.; Quintanilla-Lopez, J.E.; Santiuste, J.M., Isothermal retention indices on poly93-cyanopropylmethyl)siloxane stationary phases, J. Chromatogr. A, 2009, 1216, 10, 1630-1639, https://doi.org/10.1016/j.chroma.2008.10.025 . [all data]

Lebrón-Aguilar, Quintanilla-López, et al., 2007
Lebrón-Aguilar, R.; Quintanilla-López, J.E.; Tello, A.M.; Santiuste, J.M., Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases, J. Chromatogr. A, 2007, 1160, 1-2, 276-288, https://doi.org/10.1016/j.chroma.2007.05.025 . [all data]

Gruzdev, Alferova, et al., 2011
Gruzdev, I.V.; Alferova, M.V.; Kondratenok, B.M.; Zenkevich, I.G., Gas-chromatographic identification of chloro- and bromosubstituted anilines using retention indices, Rus. J. Anal. Chem., 2011, 66, 5, 519-524. [all data]

Gruzdev, Alferova, et al., 2011, 2
Gruzdev, I.V.; Alferova, M.V.; Kondratenok, B.M.; Zenkevich, I.G., Quantification of chloroanilines in drinking water by gas chromatography as bromo derivatives, Rus. J. Anal. Chem., 2011, 66, 10, 955-962, https://doi.org/10.1134/S1061934811100042 . [all data]

Gruzdev, Filippova, et al., 2011
Gruzdev, I.V.; Filippova, M.V.; Zenkevich, I.G.; Kondratenok, B.M., Identification of bromination products of chlorosubstituted anilines in aqueous media by using gas chromatography, Rus. J. Applied Chem., 2011, 84, 10, 1656-1667, https://doi.org/10.1134/S1070427211100132 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Peng, Yang, et al., 1991, 2
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Zc	Critical compressability factor
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.