Quinoline, 1,2,3,4-tetrahydro-
- Formula: C9H11N
- Molecular weight: 133.1903
- IUPAC Standard InChIKey: LBUJPTNKIBCYBY-UHFFFAOYSA-N
- CAS Registry Number: 635-46-1
- 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: Kusol; 1,2,3,4-Tetrahydroquinoline; Tetrahydroquinoline; 1,2,3,4-Tetrahydrochinoline
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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 | 19.6 ± 0.2 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 |
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 | 4.0 ± 0.2 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1226.18 ± 0.16 | kcal/mol | Ccr | Steele, Chirico, et al., 1989 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 57.447 | cal/mol*K | N/A | Steele, Chirico, et al., 1989, 2 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.415 | 298.15 | Steele, Chirico, et al., 1989, 2 | T = 10 to 440 K.; 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 522.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 524. | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 289.910 | K | N/A | Steele, Chirico, et al., 1989, 3 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 15.61 | kcal/mol | V | Steele, Chirico, et al., 1989 | ALS |
ΔvapH° | 15.6 | kcal/mol | N/A | Steele, Chirico, et al., 1989 | DRB |
ΔvapH° | 15.6 ± 0.05 | kcal/mol | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.8 ± 0.02 | 340. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
14.1 ± 0.02 | 380. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
13.5 ± 0.02 | 420. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
12.8 ± 0.05 | 460. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
12.1 ± 0.07 | 500. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
11.4 ± 0.1 | 540. | IP,EB | Steele, Chirico, et al., 1989 | Based on data from 323. to 572. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.823 | 290. | Acree, 1991 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
61.7 | crystaline, IV | crystaline, III | Steele, Chirico, et al., 1989, 2 | DH |
114.75 | crystaline, III | crystaline, II | Steele, Chirico, et al., 1989, 2 | DH |
231.8 | crystaline, II | crystaline, I | Steele, Chirico, et al., 1989, 2 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.8234 | 289.913 | crystaline, I | liquid | Steele, Chirico, et al., 1989, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
9.739 | 289.913 | crystaline, I | liquid | Steele, Chirico, et al., 1989, 2 | DH |
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.00 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
7.61 | EI | Loudon, Maccoll, et al., 1970 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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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Additional Data
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Source | Minkin and Tumakova, 1963 |
---|---|
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. 3168 |
Instrument | Spectrophotometer SF-4 |
Melting point | 20 |
Boiling point | 251 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of 1,2,3,4- and 5,6,7,8-tetrahydroquinolines,
J. Chem. Thermodyn., 1989, 21, 1121-1149. [all data]
Steele, Chirico, et al., 1989, 2
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of the five benzoquinolines,
J. Chem. Thermodyn., 1989, 21, 81-107. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Perkin, 1896
Perkin, W.H.,
LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds,
J. Chem. Soc., 1896, 69, 1025-1257. [all data]
Steele, Chirico, et al., 1989, 3
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Nguyen, A.; Smith, N.K.; Gammon, B.E.,
The thermodynamic properties of 1,2,3,4- and 5,6,7,8-tetrahydroquinolines,
J. Chem. Thermodyn., 1989, 21, 1121. [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]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Loudon, Maccoll, et al., 1970
Loudon, A.G.; Maccoll, A.; Wong, S.K.,
Comparison between unimolecular gas phase pyrolysis and electron impact fragmentation. Part I. The mass spectra of tetralin and some related heterocycles,
J. Chem. Soc. B, 1970, 1727. [all data]
Minkin and Tumakova, 1963
Minkin, V.I.; Tumakova, A.,
The structure and reactivity of products of condensation of aromatic amines with aliphatic aldehydes. I. Isomerism and structure of dimers of ethylidene aniline,
Zh. Obshch. Khim., 1963, 33, 637-640. [all data]
Notes
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- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion 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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