Diisopropylamine
- Formula: C6H15N
- Molecular weight: 101.1900
- IUPAC Standard InChIKey: UAOMVDZJSHZZME-UHFFFAOYSA-N
- CAS Registry Number: 108-18-9
- 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: 2-Propanamine, N-(1-methylethyl)-; (iso-C3H7)2NH; N-Isopropyl-1-amino-2-methylethane; N-(1-Methylethyl)-2-propanamine; UN 1158; N,N-Diisopropylamine; N-isopropyl-isopropylamine; N-(1-Methylethyl)-2-propamine; Bis(isopropyl)amine; NSC 6758
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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 |
---|---|---|---|---|---|
ΔfH°gas | -32.58 ± 0.62 | kcal/mol | Ccb | Ribeiro da Silva, Ribeiro da Silva, et al., 1997 | ALS |
ΔfH°gas | -34.35 | kcal/mol | N/A | Lebedeva, Katin, et al., 1971 | Value computed using ΔfHliquid° value of -178.4±0.0 kj/mol from Lebedeva, Katin, et al., 1971 and ΔvapH° value of 34.7 kj/mol from Ribeiro da Silva, Ribeiro da Silva, et al., 1997.; 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -40.87 ± 0.62 | kcal/mol | Ccb | Ribeiro da Silva, Ribeiro da Silva, et al., 1997 | |
ΔfH°liquid | -42.64 ± 0.01 | kcal/mol | Ccb | Lebedeva, Katin, et al., 1971 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1035.8 ± 0.60 | kcal/mol | Ccb | Ribeiro da Silva, Ribeiro da Silva, et al., 1997 | |
ΔcH°liquid | -1034.01 ± 0.10 | kcal/mol | Ccb | Lebedeva, Katin, et al., 1971 |
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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 357. ± 1. | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 212.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 522.2 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 523.1 | K | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.52 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 29.81 | atm | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.2978 atm; Visual; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.2 ± 0.1 | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.27 | 357.1 | N/A | Majer and Svoboda, 1985 | |
8.46 | 275. | A | Stephenson and Malanowski, 1987 | Based on data from 260. to 412. K.; AC |
8.51 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 367. K.; AC |
8.05 ± 0.02 | 313. | C | Petros, Majer, et al., 1979 | AC |
7.79 ± 0.02 | 328. | C | Petros, Majer, et al., 1979 | AC |
7.53 ± 0.02 | 343. | C | Petros, Majer, et al., 1979 | AC |
7.22 ± 0.02 | 358. | C | Petros, Majer, et al., 1979 | AC |
8.22 | 315. | EB | Petros, Majer, et al., 1979 | Based on data from 300. to 356. K.; AC |
8.2 | 291. | V | Lebedeva, Katin, et al., 1971 | ALS |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 358. | 12.86 | 0.311 | 522.2 | Majer and Svoboda, 1985 |
Reaction 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: 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
C6H14N- + =
By formula: C6H14N- + H+ = C6H15N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 390.19 ± 0.50 | kcal/mol | G+TS | Grimm and Bartmess, 1992 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.80 ± 0.40 | kcal/mol | IMRE | Grimm and Bartmess, 1992 | gas phase |
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:
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 |
---|---|---|---|---|---|
Proton affinity (review) | 232.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 224.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.6 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
7.73 ± 0.03 | PI | Watanabe and Mottl, 1957 | RDSH |
De-protonation reactions
C6H14N- + =
By formula: C6H14N- + H+ = C6H15N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 390.19 ± 0.50 | kcal/mol | G+TS | Grimm and Bartmess, 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.80 ± 0.40 | kcal/mol | IMRE | Grimm and Bartmess, 1992 | gas phase; B |
IR 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291566 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 100. | 644. | Golovnya, Zhuravleva, et al., 1982 | Chromosorb G AW (80-100 mesh); Column length: 2.7 m |
Packed | Apiezon L | 100. | 641. | Zhuravleva, Kapustin, et al., 1976 | N2 or He, Chromosorb G, AW; Column length: 2.7 m |
Packed | PMS-100 | 130. | 629. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 150. | 622. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 619. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 120. | 762. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 150. | 756. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 760. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 752. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 752. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 740. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 655. | Bartelt, 1997 | 30. m/0.32 mm/5. μm, He, 35. C @ 1. min, 10. K/min; Tend: 270. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 641. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 641. | Zenkevich, 1999 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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.
Ribeiro da Silva, Ribeiro da Silva, et al., 1997
Ribeiro da Silva, M.A.V.; Ribeiro da Silva, M.D.M.C.; Luisa, M.; Gomes, A.C.N.; Johnson, M.; Pilcher, G.,
Enthalpies of combustion of di-n-propylamine, diisopropylamine, diisobutylamine, and di-sec-butylamine,
J. Chem. Thermodyn., 1997, 29, 1025-1030. [all data]
Lebedeva, Katin, et al., 1971
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y.,
Enthalpies of formation of dipropylamine, di-isopropylamine, dibutylamine, and di-isobutylamine,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 771-772. [all data]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [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]
Toczylkin. L.S. and Young, 1980
Toczylkin. L.S.; Young, C.L.,
Gas-liquid criticl temperatures of mixtures containing electron donors. II. Amine mixtures,
J. Chem. Thermodyn., 1980, 12, 365. [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]
Petros, Majer, et al., 1979
Petros, Libor; Majer, Vladimír; Koubek, Josef; Svoboda, Václav; Pick, Jirí,
Temperature dependence of heats of vaporization, saturated vapour pressures and cohesive energies of secondary amines,
Collect. Czech. Chem. Commun., 1979, 44, 12, 3533-3540, https://doi.org/10.1135/cccc19793533
. [all data]
Grimm and Bartmess, 1992
Grimm, D.T.; Bartmess, J.E.,
The Intrinsic (Gas Phase) Basicity of some Anions Commonly Used in Condensed-Phase Synthesis,
J. Am. Chem. Soc., 1992, 114, 4, 1227, https://doi.org/10.1021/ja00030a016
. [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]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [all data]
Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R.,
Ionization potentials of ammonia and some amines,
J. Chem. Phys., 1957, 26, 1773. [all data]
Golovnya, Zhuravleva, et al., 1982
Golovnya, R.V.; Zhuravleva, I.L.; Svetlova, I.; Terenina, M.B.; Gutnik, S.B.,
Calculation of gas chromatographic retention indices of secondary amines from structural increments,
Zh. Anal. Khim., 1982, 37, 294-300. [all data]
Zhuravleva, Kapustin, et al., 1976
Zhuravleva, I.L.; Kapustin, Yu.P.; Golovnya, P.B.,
Retention indices of some isoaliphatic and heterocyclic nitrogenous bases,
Zh. Anal. Khim., 1976, 31, 1378-1380. [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]
Bartelt, 1997
Bartelt, R.J.,
Calibration of a commercial solid-phase microextraction device for measuring headspace concentrations of organic volatiles,
Anal. Chem., 1997, 69, 3, 364-372, https://doi.org/10.1021/ac960820n
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Zenkevich, 1999
Zenkevich, I.G.,
Dependence of Gas Chromatographic Retention Indices on Dynamics Molecular Characteristics,
Zh. Fiz. Khim., 1999, 73, 5, 905-910. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction 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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