Diphenylamine
- Formula: C12H11N
- Molecular weight: 169.2224
- IUPAC Standard InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
- CAS Registry Number: 122-39-4
- 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: Benzenamine, N-phenyl-; Anilinobenzene; Benzene, (phenylamino)-; DFA; DPA; N-Phenylaniline; N-Phenylbenzeneamine; Aniline, N-phenyl-; Benzene, anilino-; Big Dipper; C.I. 10355; N-Phenylbenzenamine; N,N-Diphenylamine; No-Scald; Phenylaniline; Scaldip; Deccoscald 282; Difenylamin; N-Fenylanilin; No-Scald dpa 283; Naugalube 428L; NSC 215210
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 202. | kJ/mol | Ccb | Vriens and Hill, 1952 |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 575.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 582.15 | K | N/A | Stillmann and Swain, 1899 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 326. ± 2. | K | AVG | N/A | Average of 21 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 931.15 | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 84.0997 | bar | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 4.053 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 55.23 | kJ/mol | C | Glaser and Ruland, 1957 | ALS |
ΔvapH° | 69.9 | kJ/mol | V | Vriens and Hill, 1952 | ALS |
ΔvapH° | 70.0 | kJ/mol | N/A | Vriens and Hill, 1952 | DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 110. | kJ/mol | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
64.1 | 396. | A | Stephenson and Malanowski, 1987 | Based on data from 381. to 575. K. See also Stull, 1947.; AC |
54.2 | 588. | A | Stephenson and Malanowski, 1987 | Based on data from 573. to 673. K.; 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 |
---|---|---|---|---|---|
381.5 to 575. | 5.09811 | 2729.385 | -39.207 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
110.0 ± 1.0 | 311. | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
96.7 ± 2.5 | 310. | QF | Aihara, 1953 | Based on data from 298. to 323. K. See also Cox and Pilcher, 1970.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.9 | 326.1 | DSC | Surov, Terekhova, et al., 2009 | AC |
17.86 | 326.2 | N/A | Acree, 1991 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.19 ± 0.05 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.18 ± 0.01 | PE | Debies and Rabalais, 1974 | LLK |
7.14 ± 0.03 | PI | Potapov and Iskakov, 1971 | LLK |
7.25 ± 0.03 | PI | Vilesov and Zaitsev, 1964 | RDSH |
7.44 | PE | Haink, Adams, et al., 1974 | Vertical value; LLK |
De-protonation reactions
C12H10N- + =
By formula: C12H10N- + H+ = C12H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1468. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1438. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 200. | 1619. | Huber, Kenndler, et al., 1979 | N2; Column length: 2. m |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-101 | 1567. | Alley and Dykes, 1972 | 6. K/min; Tstart: 70. C; Tend: 220. C |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-20M | 190. | 2517. | Huber, Kenndler, et al., 1979 | N2 |
Packed | PEG-20M | 190. | 2517. | Donike and Stratmann, 1976 | Chromosorb W |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SLB-5MS | 1621. | Mondello, Casilli, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 70. C; Tend: 300. C |
Capillary | SLB-5MS | 1625. | Mondello, Casilli, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 70. C; Tend: 300. C |
Capillary | DB-5 | 1622. | Kim, Paik, et al., 1997 | 30. m/0.25 mm/0.11 μm, He, 60. C @ 2. min, 4. K/min; Tend: 280. C |
Capillary | DB-5 | 1637. | Moio L., Rillo L., et al., 1996 | 30. m/0.32 mm/1. μm, H2, 3. K/min; Tstart: 40. C; Tend: 220. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1588. | Oda, Ichikawa, et al., 1996 | Program: 50C (2min) => 20C/min => 160C => 5C/min => 210C => 10C/min => 300C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 1602. | Boatright and Crum, 1997 | 30. m/0.25 mm/0.1 μm, He, 50. C @ 2. min, 5. K/min, 300. C @ 3. min |
Capillary | DB-5 | 1637. | Moio, Dekimpe, et al., 1993 | 30. m/0.32 mm/1. μm, H2, 3. K/min; Tstart: 40. C; Tend: 220. C |
Capillary | Ultra-1 | 1568. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Capillary | SE-54 | 1617. | Harland, Cumming, et al., 1986 | He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 5 % Phenyl methyl siloxane | 1634. | Department of Food Safety and Welfare, 2006 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C(1 min) 25 0C/min -> 125 0C 10 0C/min -> 300 0C (10 min) |
Capillary | OV-1 | 1575. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1575. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Other | Methyl Silicone | 1601. | Ardrey and Moffat, 1981 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Superox 0.6; Carbowax 20M | 2521. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 2521. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 274.57 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5MS | 276.00 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
Capillary | SE-52 | 279.32 | Hasegawa, Usami, et al., 1990 | 2. K/min; Column length: 12. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 270. C |
Capillary | OV-101 | 275.74 | Blanco, Blanco, et al., 1989 | H2, 4. K/min; Column length: 25. m; Column diameter: 0.22 mm; Tstart: 50. C; Tend: 300. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 279.27 | Hasegawa, Usami, et al., 1990 | Column length: 12. m; Column diameter: 0.25 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Stillmann and Swain, 1899
Stillmann, J.M.; Swain, R.E.,
The melting heat of naphthylamine and diphenylamine in relation to their lowering of molecular freezing point,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1899, 29, 705. [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]
Surov, Terekhova, et al., 2009
Surov, Artem O.; Terekhova, Irina V.; Bauer-Brandl, Annette; Perlovich, German L.,
Thermodynamic and Structural Aspects of Some Fenamate Molecular Crystals,
Crystal Growth & Design, 2009, 9, 7, 3265-3272, https://doi.org/10.1021/cg900002q
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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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
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. [all data]
Aihara, 1953
Aihara, A.,
J. Chem. Soc. Jpn. Pure Chem. Sect., 1953, 74, 437. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
Potapov and Iskakov, 1971
Potapov, V.K.; Iskakov, L.I.,
Electronic structure and photoionization of aromatic amines,
High Energy Chem., 1971, 5, 237, In original 264. [all data]
Vilesov and Zaitsev, 1964
Vilesov, F.I.; Zaitsev, V.M.,
Photoionization of phenyl derivatives of group 5 elements,
Dokl. Akad. Nauk SSSR, 1964, 154, 886, In original 117. [all data]
Haink, Adams, et al., 1974
Haink, H.J.; Adams, J.E.; Huber, J.R.,
The electronic structure of aromatic amines: photoelectron spectroscopy of diphenylamine, iminobibenzyl, acridan and carbazole,
Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 436. [all data]
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Huber, Kenndler, et al., 1979
Huber, J.F.K.; Kenndler, E.; Reich, G.,
Quantitation of the Information Content of Multi-Dimensional Gas Chromatography and Low- Resolution Mass Spectrometry in the Identification of Doping Drugs,
J. Chromatogr., 1979, 172, 1, 15-30, https://doi.org/10.1016/S0021-9673(00)90941-5
. [all data]
Alley and Dykes, 1972
Alley, B.J.; Dykes, H.W.H.,
Gas-Liquid Chromatographic Determination of Nitrate Esters,Stabilizers and Plasticizers in Nitrocellulose-Base Propellants,
J. Chromatogr., 1972, 71, 1, 23-37, https://doi.org/10.1016/S0021-9673(01)85687-9
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Donike and Stratmann, 1976
Donike, M.; Stratmann, D.,
Gas-chromatographische identifizierung von stimulantien der phenyläthylaminreihe mit hilfe der retnetions-indices,
Z. Anal. Chem., 1976, 279, 2, 129-131, https://doi.org/10.1007/BF00440798
. [all data]
Mondello, Casilli, et al., 2007
Mondello, L.; Casilli, A.; Tranchida, P.Q.; Presti, M.L.; Dugo, P.; Dugo, G.,
Comprehensive gas chromatography coupled to mass spectrometry for the separation of pesticides in a very complex matrix,
Anal. Bioanal. Chem., 2007, 389, 6, 1755-1763, https://doi.org/10.1007/s00216-007-1412-y
. [all data]
Kim, Paik, et al., 1997
Kim, K.R.; Paik, M.J.; Kim, J.H.; Dong, S.W.; Jeong, D.H.,
Rapid gas chromatographic profiling and screening of biologically active amines,
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Moio L., Rillo L., et al., 1996
Moio L.; Rillo L.; Ledda A.; Addeo F.,
Odorous constituents of ovine milk in relationship to diet,
J. Dairy Sci., 1996, 79, 8, 1322-1331, https://doi.org/10.3168/jds.S0022-0302(96)76488-3
. [all data]
Oda, Ichikawa, et al., 1996
Oda, J.; Ichikawa, S.; Mori, T.,
Analysis of polycyclic aromatic hydrocarbons in airborne particulates by capillary GC/MS method with programmed temperature relative retention index,
Bunseki Kagaku, 1996, 45, 9, 825-835, https://doi.org/10.2116/bunsekikagaku.45.825
. [all data]
Boatright and Crum, 1997
Boatright, W.L.; Crum, A.D.,
Nonpolar-volatile lipids from soy protein isolates and hexane-defatted flakes,
J. Amer. Oil Chem. Soc., 1997, 74, 4, 461-467, https://doi.org/10.1007/s11746-997-0107-z
. [all data]
Moio, Dekimpe, et al., 1993
Moio, L.; Dekimpe, J.; Etievant, P.; Addeo, F.,
Neutral volatile compounds in the raw milks from different species,
J. Dairy Res., 1993, 60, 2, 199-213, https://doi.org/10.1017/S0022029900027515
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E.,
The Kovats indexes of some organic micropollutants on an SE54 capillary column,
EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]
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Department of Food Safety, Ministry of Health; Welfare,
Analytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods, 2006, retrieved from http://www.mhlw.go.jp/english/topics/foodsafety/positivelist060228/de/060526-1a.pdf. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
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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,
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. [all data]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Hasegawa, Usami, et al., 1990
Hasegawa, K.; Usami, S.; Higashide, A.,
Analysis of amino polycyclic aromatic hydrocarbons and polycyclic aromatic nitrogen heterocycles,
Nippon Kagaku Kaishi, 1990, 7, 777-788, https://doi.org/10.1246/nikkashi.1990.777
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Blanco, Blanco, et al., 1989
Blanco, C.G.; Blanco, J.; Bermejo, J.; Guillen, M.D.,
Capillary gas chromatography of some polycyclic aromatic compounds on several stationary phases,
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Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation 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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