Naphthalene, 1-bromo-
- Formula: C10H7Br
- Molecular weight: 207.067
- IUPAC Standard InChIKey: DLKQHBOKULLWDQ-UHFFFAOYSA-N
- CAS Registry Number: 90-11-9
- 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: α-Bromonaphthalene; α-Naphthyl bromide; 1-Bromonaphthalene; 1-Naphthyl bromide
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Phase change data
Go To: Top, 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 554.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 554.25 | K | N/A | Cooper, Crowne, et al., 1967 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 275. | K | N/A | Khanna, Khetarpal, et al., 1981 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 279.25 | K | N/A | Deffet, 1940 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 279.25 | K | N/A | Timmermans and Hennaut-Roland, 1937 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 63.9 ± 0.4 | kJ/mol | GS | Verevkin, 2003 | Based on data from 303. to 336. K.; AC |
ΔvapH° | 62.7 ± 5.0 | kJ/mol | E | Ribeiro da Silva, Ferrao, et al., 1993 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
58.5 | 372. | N/A | Stephenson and Malanowski, 1987 | Based on data from 357. to 555. K.; AC |
45.8 | 484. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 469. to 559. K. See also Hon, Singh, et al., 1976 and Dykyj, Svoboda, et al., 1999.; AC |
56. ± 6. | 329. | ME | Urbani, Gigli, et al., 1980 | Based on data from 295. to 359. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.16 | 271.4 | Acree, 1991 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, 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
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.08 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.08 ± 0.03 | TRPI | Gotkis, Naor, et al., 1993 | LL |
8.09 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C10H7+ | 11.3 ± 0.1 | Br | DER | Gotkis, Naor, et al., 1993 | LL |
C10H7+ | 12.1 ± 0.1 | Br | TRPI | Gotkis, Naor, et al., 1993 | LL |
De-protonation reactions
By formula: C10H6Br- + H+ = C10H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1619. ± 15. | kJ/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 15. | kJ/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
C10H6Br- + =
By formula: C10H6Br- + H+ = C10H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1621. ± 15. | kJ/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1588. ± 15. | kJ/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Cooper, Crowne, et al., 1967
Cooper, A.R.; Crowne, C.W.P.; Farrell, P.G.,
Gas-Liquid Chromatographic Studies of Electron-Donor-Acceptor Systems,
Trans. Faraday Soc., 1967, 63, 447. [all data]
Khanna, Khetarpal, et al., 1981
Khanna, M.S.; Khetarpal, S.C.; Lal, K.; Bhatnagar, H.L.,
Thermodynamic studies on melting of some alpha- and beta-halogen derivatives of napthalene,
Indian J. Chem> Sect. A, 1981, 20, 544. [all data]
Deffet, 1940
Deffet, L.,
Piezometric Research. Temperatures of Fusion and Transformation,
Bull. Soc. Chim. Belg., 1940, 49, 223. [all data]
Timmermans and Hennaut-Roland, 1937
Timmermans, J.; Hennaut-Roland, M.,
Works from International Bureau at Physical-Chemical Standards. VIII. Physical constants of 20 organic compounds,
J. Chim. Phys. Phys.-Chim. Biol., 1937, 34, 693. [all data]
Verevkin, 2003
Verevkin, Sergey P.,
Vapor pressures and enthalpies of vaporization of a series of 1- and 2-halogenated naphthalenes,
The Journal of Chemical Thermodynamics, 2003, 35, 8, 1237-1251, https://doi.org/10.1016/S0021-9614(03)00051-X
. [all data]
Ribeiro da Silva, Ferrao, et al., 1993
Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Lopes, A.J.M.,
Enthalpies of combustion of each of the two bromonaphthalenes,
J. Chem. Thermodyn., 1993, 25, 229-235. [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]
Hon, Singh, et al., 1976
Hon, Huynh C.; Singh, Rakesh P.; Kudchadker, Arvind P.,
Vapor pressure-boiling point measurements of five organic substances by twin ebulliometry,
J. Chem. Eng. Data, 1976, 21, 4, 430-431, https://doi.org/10.1021/je60071a011
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Urbani, Gigli, et al., 1980
Urbani, Maria; Gigli, Rosario; Piacente, Vincenzo,
Vaporization study of .alpha.-bromonaphthalene,
J. Chem. Eng. Data, 1980, 25, 2, 97-100, https://doi.org/10.1021/je60085a002
. [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]
Gotkis, Naor, et al., 1993
Gotkis, Y.; Naor, M.; Laskin, J.; Lifshitz, C.; Faulk, J.D.; Dunbar, R.C.,
Time-resolved dissociation of bromonaphthalene ion studied by TPIMS and TRPD. Heat of formation of naphthyl ion,
J. Am. Chem. Soc., 1993, 115, 7402. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R.,
Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method,
J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion 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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