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Benzylamine

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Gas 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
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas87.8 ± 2.7kJ/molCcbCarson, Laye, et al., 1977ALS
Deltafgas56.6kJ/molN/ALemoult, 1907Value computed using «DELTA»fHliquid° value of 3.0 kj/mol from Lemoult, 1907 and «DELTA»vapH° value of 53.6 kj/mol from Carson, Laye, et al., 1977.; DRB

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
Deltafliquid34.2 ± 1.7kJ/molCcbCarson, Laye, et al., 1977ALS
Deltafliquid3.kJ/molCcbLemoult, 1907ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4075.0 ± 1.7kJ/molCcbCarson, Laye, et al., 1977ALS
Deltacliquid-4058.kJ/molCcbLemoult, 1907ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
207.18298.15Nichols and Wads, 1975DH

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil440. ± 70.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Deltavap60.16kJ/molN/AMajer and Svoboda, 1985 
Deltavap54.6 ± 0.3kJ/molN/AMokbel, Razzouk, et al., 2009Based on data from 293. - 362. K.; AC
Deltavap54. ± 2.kJ/molVCarson, Laye, et al., 1977ALS
Deltavap53.6kJ/molN/ACarson, Laye, et al., 1977DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
363.20.016Weast and Grasselli, 1989BS
363.0.016Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
52.7 ± 0.3328.N/AMokbel, Razzouk, et al., 2009Based on data from 293. - 362. K.; AC
51.8317.AStephenson and Malanowski, 1987Based on data from 302. - 458. K. See also Carson, Laye, et al., 1977 and Beersmans and Jungers, 2010.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
302. - 457.74.82712003.528-41.973Stull, 1947Coefficents calculated by NIST from author's data.

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:


Gas phase ion energetics data

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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 C7H9N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)913.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity879.4kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
922.7 ± 7.8Wind, Papp, et al., 2005T = 298K; MM
924. ± 4.Cao and Holmes, 2000Authors recommend revision of Hunter and Lias, 1998 value based on their KM results, while results for other alkylamines are consistent with the Hunter and Lias, 1998 tabulated values.; MM

Protonation entropy at 298K

Protonation entropy (J/mol*K) Reference Comment
-3. ± 10.Wind, Papp, et al., 2005T = 298K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.49 ± 0.06EISelim, Rabbih, et al., 1987LBLHLM
8.8PEAue and Bowers, 1979LLK
8.73PEBodor, Dewar, et al., 1970RDSH
8.64 ± 0.05PIVilesov and Terenin, 1957RDSH
9.46PEDeshmukh, Dutta, et al., 1982Vertical value; LBLHLM
9.10 ± 0.01PEDebies and Rabalais, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH4N+10.08 ± 0.05C6H5EIHolmes and Lossing, 1984LBLHLM
C5H3+17.68 ± 0.13NH+C2H5EISelim, Rabbih, et al., 1989LL
C5H3+17.23 ± 0.11NH2+H2+C2H2EISelim, Rabbih, et al., 1989LL
C5H3+16. ± 0.NH2+C2H4EISelim, Rabbih, et al., 1989LL
C6H6+10.29 ± 0.05?EISelim, Rabbih, et al., 1992LL
C6H7+12.17 ± 0.06HCNEISelim, Rabbih, et al., 1987, 2LBLHLM
C7H6+12.06 ± 0.10NH3EISelim, Rabbih, et al., 1987, 3LBLHLM
C7H7+11.75 ± 0.06NH2EISelim, Rabbih, et al., 1987, 2LBLHLM
C7H7N+9.35 ± 0.07H2PIAkopyan, Vilesov, et al., 1962RDSH
C7H8N+9.25 ± 0.06HEISelim, Rabbih, et al., 1987LBLHLM
C7H8N+9.3 ± 0.1HPIAkopyan and Vilesov, 1964RDSH
C7H8N+9.21 ± 0.07HPIAkopyan, Vilesov, et al., 1962RDSH

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.
Origin R.L.FOLTZ BATTELLE MEMORIAL INST., COLUMBUS LAB., OHIO, USA
NIST MS number 20081

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

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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: 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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Additional Data

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Source Grammaticakis, 1947
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. 427
Instrument n.i.g.
Boiling point 185; 90(12)

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, 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

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Column type Active phase Temperature (C) I Reference Comment
PackedSE-30180.1035.Oszczapowicz, Osek, et al., 1985N2, Chromosorb A AW; Column length: 3. m
PackedSE-30180.1035.Oszczapowicz, Osek, et al., 1984N2, Chromosorb W AW; Column length: 3. m

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

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Column type Active phase I Reference Comment
CapillaryOV-1983.9Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C

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

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Column type Active phase I Reference Comment
CapillaryHP-5MS1019.2Andriamaharavo, 201430. m/0.25 mm/0.25 «mu»m, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

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

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Column type Active phase I Reference Comment
CapillaryDB-Wax1307.Shimoda, Peralta, et al., 199660. m/0.25 mm/0.25 «mu»m, He, 3. K/min; Tstart: 50. C; Tend: 230. C

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

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes994.Zenkevich and Chupalov, 1996Program: not specified
OtherMethyl Silicone995.Ardrey and Moffat, 1981Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

Carson, Laye, et al., 1977
Carson, A.S.; Laye, P.G.; Yrekli, M., The enthalpy of formation of benzylamine, J. Chem. Thermodyn., 1977, 9, 827-829. [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]

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]

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]

Mokbel, Razzouk, et al., 2009
Mokbel, Ilham; Razzouk, Antonio; Sawaya, Terufat; Jose, Jacques, Experimental Vapor Pressures of 2-Phenylethylamine, Benzylamine, Triethylamine, and cis -2,6-Dimethylpiperidine in the Range between 0.2 Pa and 75 kPa, J. Chem. Eng. Data, 2009, 54, 3, 819-822, https://doi.org/10.1021/je800603z . [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]

Beersmans and Jungers, 2010
Beersmans, J.; Jungers, J.C., Synthèse et Étude des Chlorure, Bromure et Iodure de Deutérométhyle, Bull. Soc. Chim. Belges, 2010, 56, 5-8, 238-250, https://doi.org/10.1002/bscb.19470560506 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

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]

Wind, Papp, et al., 2005
Wind, J.J.; Papp, L.; Happel, M.; Hahn, K.; Andriole, E.J.; Poutsma, J.C., Proton Affinity of beta-Oxalylaminoalanine (BOAA): Incorporation of Direct Entropy Correction into the Single-Reference Kinetic Method, J. Am. Soc. Mass Spectrom., 2005, 16, 1151. [all data]

Cao and Holmes, 2000
Cao, J.; Holmes, J.L., The proton affinity of amine-alkanes. A test case for the kinetic method, Int. J. Mass Spectrom., 2000, 195/196, 525. [all data]

Selim, Rabbih, et al., 1987
Selim, E.T.; Rabbih, M.A.; Fahmey, M.A., M and [M-1]+ ions formed for benzyl alcohol, benzyl amine and benzyl cyanide, Org. Mass Spectrom., 1987, 22, 381. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Jennings, W.B.; Worley, S.D., Photoelectron spectra of molecules-IV.Ionization potentials and heats of formation of some hydrazines and amines, Tetrahedron, 1970, 26, 4109. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Deshmukh, Dutta, et al., 1982
Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P., Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters, J. Am. Chem. Soc., 1982, 104, 1740. [all data]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [all data]

Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P., Heats of formation of organic radicals from appearance energies, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]

Selim, Rabbih, et al., 1989
Selim, E.T.M.; Rabbih, M.A.; Fahmey Ahmad, M.A.; Shalbi, A.S., Energetic study of [C5H3]+ fragment ion produced from some benzyl derivatives, Arab Gulf J. Sci. Res., 1989, 7, 53. [all data]

Selim, Rabbih, et al., 1992
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F., Electron impact study of [C6H6]+ fragment ions produced from isomeric C7H9N precursors using the deconvoluted first differential technique and kinetic release measurements, Int. J. Mass Spectrom. Ion Processes, 1992, 113, 133. [all data]

Selim, Rabbih, et al., 1987, 2
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A., A mass spectrometric study of [C7H7]+ and [C6H7]+ fragment ions obtained from benzyl alcohol, benzyl amine and benzyl cyanide, Egypt. J. Phys., 1987, 18, 37. [all data]

Selim, Rabbih, et al., 1987, 3
Selim, E.T.; Rabbih, M.A.; Rezk, A.M.H.; Fahmey, M.A., Energetics of [C7H6]+ fragment ion using electron impact technique, Indian J. Pure Appl. Phys., 1987, 25, 451. [all data]

Akopyan, Vilesov, et al., 1962
Akopyan, M.E.; Vilesov, F.I.; Terenin, A.N., A mass-spectroscopic study of the spectral dependence of the efficiency of photoionization of benzene derivatives, Dokl. Akad. Nauk SSSR 1961,140,1037 (Engl. Transl.: Soviet Phys. - Dokl., 1962, 6, 890). [all data]

Akopyan and Vilesov, 1964
Akopyan, M.E.; Vilesov, F.I., Excited states of positive ions and dissociative photoionization of aromatic amines, Dokl. Akad. Nauk SSSR, 1964, 158, 1386, In original 965. [all data]

Grammaticakis, 1947
Grammaticakis, P., Contribution a l'etude spectrale de quelques derives de l'isocyanate de phenyle. I. Absorption dans l'ultra-violet moyen des derives phenylcarbamyles de quelques amines, hydroxylamines, phenylhydrazines, cetimines et oximes, Bull. Soc. Chim. Fr., 1947, 14, 664-674. [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]

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]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References