Benzylamine
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChIKey: WGQKYBSKWIADBV-UHFFFAOYSA-N
- CAS Registry Number: 100-46-9
- 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. - Other names: Benzenemethanamine; α-Aminotoluene; ω-Aminotoluene; (Phenylmethyl)amine; Monobenzylamine; N-Benzylamine; Sumine 2005; (Aminomethyl)benzene; NSC 8046; Phenylmethanamine; 857483-23-9; 858831-93-3
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 20.98 ± 0.65 | kcal/mol | Ccb | Carson, Laye, et al., 1977 | ALS |
ΔfH°gas | 13.5 | kcal/mol | N/A | Lemoult, 1907 | Value computed using ΔfHliquid° value of 3.0 kj/mol from Lemoult, 1907 and ΔvapH° 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 |
---|---|---|---|---|---|
ΔfH°liquid | 8.18 ± 0.41 | kcal/mol | Ccb | Carson, Laye, et al., 1977 | ALS |
ΔfH°liquid | 0.6 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -973.95 ± 0.41 | kcal/mol | Ccb | Carson, Laye, et al., 1977 | ALS |
ΔcH°liquid | -970.0 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
49.517 | 298.15 | Nichols and Wads, 1975 | 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:
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 |
---|---|---|---|---|---|
Tboil | 440. ± 70. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.38 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 13.0 ± 0.07 | kcal/mol | N/A | Mokbel, Razzouk, et al., 2009 | Based on data from 293. to 362. K.; AC |
ΔvapH° | 12.8 ± 0.5 | kcal/mol | V | Carson, Laye, et al., 1977 | ALS |
ΔvapH° | 12.8 | kcal/mol | N/A | Carson, Laye, et al., 1977 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
363.2 | 0.016 | Weast and Grasselli, 1989 | BS |
363. | 0.016 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.6 ± 0.07 | 328. | N/A | Mokbel, Razzouk, et al., 2009 | Based on data from 293. to 362. K.; AC |
12.4 | 317. | A | Stephenson and Malanowski, 1987 | Based on data from 302. to 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 (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
302. to 457.7 | 4.8214 | 2003.528 | -41.973 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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) | 218.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 210.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
220.5 ± 1.9 | Wind, Papp, et al., 2005 | T = 298K; MM |
221. ± 1. | Cao and Holmes, 2000 | Authors 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 (cal/mol*K) | Reference | Comment |
---|---|---|
-0.7 ± 2.4 | Wind, Papp, et al., 2005 | T = 298K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.49 ± 0.06 | EI | Selim, Rabbih, et al., 1987 | LBLHLM |
8.8 | PE | Aue and Bowers, 1979 | LLK |
8.73 | PE | Bodor, Dewar, et al., 1970 | RDSH |
8.64 ± 0.05 | PI | Vilesov and Terenin, 1957 | RDSH |
9.46 | PE | Deshmukh, Dutta, et al., 1982 | Vertical value; LBLHLM |
9.10 ± 0.01 | PE | Debies and Rabalais, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4N+ | 10.08 ± 0.05 | C6H5 | EI | Holmes and Lossing, 1984 | LBLHLM |
C5H3+ | 17.68 ± 0.13 | NH+C2H5 | EI | Selim, Rabbih, et al., 1989 | LL |
C5H3+ | 17.23 ± 0.11 | NH2+H2+C2H2 | EI | Selim, Rabbih, et al., 1989 | LL |
C5H3+ | 16. ± 0. | NH2+C2H4 | EI | Selim, Rabbih, et al., 1989 | LL |
C6H6+ | 10.29 ± 0.05 | ? | EI | Selim, Rabbih, et al., 1992 | LL |
C6H7+ | 12.17 ± 0.06 | HCN | EI | Selim, Rabbih, et al., 1987, 2 | LBLHLM |
C7H6+ | 12.06 ± 0.10 | NH3 | EI | Selim, Rabbih, et al., 1987, 3 | LBLHLM |
C7H7+ | 11.75 ± 0.06 | NH2 | EI | Selim, Rabbih, et al., 1987, 2 | LBLHLM |
C7H7N+ | 9.35 ± 0.07 | H2 | PI | Akopyan, Vilesov, et al., 1962 | RDSH |
C7H8N+ | 9.25 ± 0.06 | H | EI | Selim, Rabbih, et al., 1987 | LBLHLM |
C7H8N+ | 9.3 ± 0.1 | H | PI | Akopyan and Vilesov, 1964 | RDSH |
C7H8N+ | 9.21 ± 0.07 | H | PI | Akopyan, Vilesov, et al., 1962 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 180. | 1035. | Oszczapowicz, Osek, et al., 1985 | N2, Chromosorb A AW; Column length: 3. m |
Packed | SE-30 | 180. | 1035. | Oszczapowicz, Osek, et al., 1984 | N2, Chromosorb W AW; Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 983.9 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1019.2 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1307. | Shimoda, Peralta, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 994. | Zenkevich and Chupalov, 1996 | Program: not specified |
Other | Methyl Silicone | 995. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]
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, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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