Naphthalene, 1,2,3,4-tetrahydro-
- Formula: C10H12
- Molecular weight: 132.2023
- IUPAC Standard InChIKey: CXWXQJXEFPUFDZ-UHFFFAOYSA-N
- CAS Registry Number: 119-64-2
- 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. - Isotopologues:
- Other names: Tetralin; Benzocyclohexane; Tetrahydronaphthalene; Tetraline; Tetranap; 1,2,3,4-Tetrahydronaphthalene; Naphthalene-1,2,3,4-tetrahydride; δ(5,7,9)-Naphthantriene; Bacticin; Tetralina; NSC 77451; tetralene
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Condensed phase thermochemistry data
Go To: Top, 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 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 | -6.83 ± 0.25 | kcal/mol | Ccb | Good and Lee, 1976 | ALS |
ΔfH°liquid | -7.79 ± 0.52 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -7.91 ± 0.51 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1343.58 ± 0.21 | kcal/mol | Ccb | Good and Lee, 1976 | Corresponding ΔfHºliquid = -6.82 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1342.61 ± 0.51 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | Corresponding ΔfHºliquid = -7.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1338.1 | kcal/mol | Ccb | Karo, McLaughlin, et al., 1953 | Corrected from net heat of combustion; Corresponding ΔfHºliquid = -12.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1334.1 | kcal/mol | Ccb | Hock and Knauel, 1951 | Corresponding ΔfHºliquid = -16.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 60.100 | cal/mol*K | N/A | McCullough, Finke, et al., 1957 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.969 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 320 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 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 | 480. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 237.3 ± 0.9 | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 237.3400 | K | N/A | McCullough, Finke, et al., 1957, 2 | Uncertainty assigned by TRC = 0.07 K; TRC |
Ttriple | 237.3500 | K | N/A | McCullough, Finke, et al., 1957, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 720. ± 1. | K | N/A | Tsonopoulos and Ambrose, 1995 | |
Tc | 721.7 | K | N/A | Gude and Teja, 1994 | Uncertainty assigned by TRC = 0.5 K; by the flow method; TRC |
Tc | 719.9 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 721. | K | N/A | Steele, Chirico, et al., 1988 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 36.0 ± 1. | atm | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 35.83 | atm | N/A | Gude and Teja, 1994 | Uncertainty assigned by TRC = 0.25 atm; by the flow method; TRC |
Pc | 37.01 | atm | N/A | Steele, Chirico, et al., 1988 | Uncertainty assigned by TRC = 0.79 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.408 | l/mol | N/A | Tsonopoulos and Ambrose, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.5 ± 0.1 | mol/l | N/A | Tsonopoulos and Ambrose, 1995 | |
ρc | 2.45 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.05 mol/l; TRC |
ρc | 2.27 | mol/l | N/A | Steele, Chirico, et al., 1988 | Uncertainty assigned by TRC = 0.11 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.2 ± 0.3 | kcal/mol | V | Boyd, Sanwal, et al., 1971 | ALS |
ΔvapH° | 14.0 | kcal/mol | N/A | Boyd, Sanwal, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.5 | 480. | N/A | Lee, Dempsey, et al., 1992 | Based on data from 465. to 580. K.; AC |
12.2 | 326. | A | Stephenson and Malanowski, 1987 | Based on data from 311. to 481. K.; AC |
9.87 ± 0.02 | 498. | C | Natarajan and Viswanath, 1985 | AC |
8.99 ± 0.02 | 552. | C | Natarajan and Viswanath, 1985 | AC |
8.53 ± 0.02 | 567. | C | Natarajan and Viswanath, 1985 | AC |
8.10 ± 0.02 | 585. | C | Natarajan and Viswanath, 1985 | AC |
7.65 ± 0.02 | 604. | C | Natarajan and Viswanath, 1985 | AC |
12.5 | 346. | N/A | Katayama and Harada, 1984 | Based on data from 331. to 437. K.; AC |
11.6 | 382. | N/A | Stull, 1947 | Based on data from 367. to 479. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
367.0 to 479.4 | 4.12100 | 1690.912 | -70.229 | Herz and Schuftan, 1922 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.9749 | 237.36 | McCullough, Finke, et al., 1957 | DH |
2.976 | 237.4 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.53 | 237.36 | McCullough, Finke, et al., 1957 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - 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
View reactions leading to C10H12+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.46 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 193.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 186.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
191.4 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
185.0 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.44 | EI | Dass and Gross, 1985 | LBLHLM |
8.48 ± 0.05 | EQ | Mautner(Meot-Ner), 1980 | LLK |
8.47 | CTS | Pitt, 1970 | RDSH |
8.73 | EI | Loudon, Maccoll, et al., 1970 | RDSH |
9.14 ± 0.05 | EI | Meier, Heiss, et al., 1968 | RDSH |
8.45 ± 0.02 | PE | Maier and Turner, 1973 | Vertical value; LLK |
8.44 | PE | Brogli, Giovannini, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C8H8+ | 11.31 | ? | EI | Loudon, Maccoll, et al., 1970 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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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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 | CONTINENTAL OIL CO., PONCA CITY, OKLA, USA |
NIST MS number | 34859 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Good and Lee, 1976
Good, W.D.; Lee, S.H.,
The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons,
J. Chem. Thermodyn., 1976, 8, 643-650. [all data]
Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D.,
The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons,
J. Phys. Chem., 1971, 75, 1264-1271. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Karo, McLaughlin, et al., 1953
Karo, W.; McLaughlin, R.L.; Hipsher, H.F.,
Dicyclic hydrocarbons. VI. 1,2,3,4-Tetrahydronaphthalene and 1-alkyl-1,2,3,4-tetrahydronaphthalenes,
J. Am. Chem. Soc., 1953, 75, 3233-3235. [all data]
Hock and Knauel, 1951
Hock, I.H.; Knauel, G.,
Autoxydation von kohlenwasserstoffen, XIV. Mitteil. Uber die energetische stellung organischer hydroperoxyde,
Chem. Ber., 1951, 84, 1-5. [all data]
McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Kincheloe, T.C.; Waddington, G.,
The low temperature thermodynamic properties of naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1,2,3,4-tetrahydronaphthalene, trans-decahydronaphthalene and cis-decahydronaphthalene,
J. Phys. Chem., 1957, 61, 1105-1116. [all data]
McCullough, Finke, et al., 1957, 2
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Todd, S.S.; Kincheloe, T.C.; Waddington, G.,
The Low-Temperature Thermodynamic Properties of Naphthalene, 1-Methylnaphthalene, 2-Methylnaphthalene, 1,2,3,4-tetrahydro- naphthalene, trans-decahydronaphthalene and cis-Decahydronaphthalene,
J. Phys. Chem., 1957, 61, 1105. [all data]
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
J. Chem. Eng. Data, 1995, 40, 547-558. [all data]
Gude and Teja, 1994
Gude, M.T.; Teja, A.S.,
The Critical Properties of Several n-Alkanals, Tetralin and NMP,
Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Series No. 2, p.174-83. [all data]
Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J.,
The critical properties of thermally stable and unstable fluids. II. 1986 results,
AIChE Symp. Ser., 1990, 86, 279, 122-7. [all data]
Steele, Chirico, et al., 1988
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Smith, N.K.,
, Report, NIPPR-395, 1988. [all data]
Lee, Dempsey, et al., 1992
Lee, Chang Ha; Dempsey, Dennis M.; Mohamed, Rahoma S.; Holder, Gerald D.,
Vapor-liquid equilibria in the systems of n-decane/tetralin, n-hexadecane/tetralin, n-decane/1-methylnaphthalene, and 1-methylnaphthalene/tetralin,
J. Chem. Eng. Data, 1992, 37, 2, 183-186, https://doi.org/10.1021/je00006a012
. [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]
Natarajan and Viswanath, 1985
Natarajan, Govindarajan; Viswanath, Dabir S.,
Enthalpy of vaporization and vapor pressure of benzene, toluene, p-xylene, and tetralin between 1 and 16 bar,
J. Chem. Eng. Data, 1985, 30, 2, 137-140, https://doi.org/10.1021/je00040a001
. [all data]
Katayama and Harada, 1984
Katayama, Hirotake; Harada, Yasuhiro,
Vapor pressure measurement of Tetralin at reduced pressures,
J. Chem. Eng. Data, 1984, 29, 4, 373-375, https://doi.org/10.1021/je00038a002
. [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]
Herz and Schuftan, 1922
Herz, W.; Schuftan, P.,
Physikalisch-chemische Untersuchungen an Tetralin und Dekalin,
Z. Phys. Chem. (Frankfurt/Main), 1922, 101, 269-285. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D.,
Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons,
Int. J. Mass Spectrom., 2000, 201, 283. [all data]
Dass and Gross, 1985
Dass, C.; Gross, M.L.,
The question of cyclic versus acyclic ions: The structure of [C6H10]+ gas phase ions,
Org. Mass Spectrom., 1985, 20, 34. [all data]
Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M.,
Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite,
J. Phys. Chem., 1980, 84, 2716. [all data]
Pitt, 1970
Pitt, C.G.,
Hyperconjugation: An alternative to the concept of the pπ-dπ bond in Group IV chemistry,
J. Organomet. Chem., 1970, 23, 35. [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]
Meier, Heiss, et al., 1968
Meier, H.; Heiss, J.; Suhr, H.; Muller, E.,
Energetische Untersuchungen zum Mills-Nixon-Effekt. Ionisierungsenergien von Benzolmolekulen mit ankondensierten gesattigten Ringen,
Tetrahedron, 1968, 24, 2307. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]
Brogli, Giovannini, et al., 1973
Brogli, F.; Giovannini, E.; Heilbronner, E.; Schurter, R.,
Die photoelektronen spektren der benzocycloalkene,
Chem. Ber., 1973, 106, 961. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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