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1,4-Benzenedicarboxylic acid, dimethyl ester

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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
Deltafsolid-710.0kJ/molCcbKaryakin, Rabinovich, et al., 1978ALS
Deltafsolid-732.6 ± 1.0kJ/molCcbColomina, Laynez, et al., 1972ALS
Quantity Value Units Method Reference Comment
Deltacsolid-4631.66 ± 0.88kJ/molCcbColomina, Laynez, et al., 1972Corresponding «DELTA»fsolid = -732.59 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
261.1298.15Elliott and Chris, 1968T = 30 to 200°C.; DH
276.1353.Smith and Dole, 1956T = 80 to 190°C. Equation only.; 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus415.2KN/ADozen, Fujishima, et al., 1978Uncertainty assigned by TRC = 0.2 K; TRC
Tfus413.80KN/AElliott and Chris, 1968, 2Uncertainty assigned by TRC = 0.01 K; TRC
Tfus413.8KN/ASmith and Dole, 1956, 2Uncertainty assigned by TRC = 0.2 K; TRC
Tfus413.KN/AShirley and Reedy, 1951Uncertainty assigned by TRC = 4. K; TRC
Tfus413.KN/AHennion and Kurtz, 1943Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Deltasub104.6 ± 0.3kJ/molCRoux, Jimenez, et al., 1998ALS
Deltasub104.6 ± 0.3kJ/molN/AVictoria Roux, Jime´nez, et al., 1998AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
62.428.AStephenson and Malanowski, 1987Based on data from 413. - 523. K.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
103.8 ± 0.3321.MEVictoria Roux, Jime´nez, et al., 1998Based on data from 311. - 330. K.; AC
94.4388.N/AStephenson and Malanowski, 1987Based on data from 373. - 413. K.; AC
88.3393.GSKraus, Beranek, et al., 1962Based on data from 373. - 413. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
32.000415.4Karyakin and Shvetsova, 1982DH
31.631413.79Elliott and Chris, 1968DH
32.100413.8Smith and Dole, 1956DH
32.09413.8Acree, 1993AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
77.0415.4Karyakin and Shvetsova, 1982DH
76.44413.79Elliott and Chris, 1968DH
77.6413.8Smith and Dole, 1956DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Quantity Value Units Method Reference Comment
Proton affinity (review)843.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity812.3kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.824 ± 0.087IMREMishima, Huh, et al., 1995«DELTA»Gea(343 K)=-20.2 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B
0.824 ± 0.087IMREHuh, Kang, et al., 1999«DELTA»G(EA) 343K; anchored to «DELTA»G value. Including anchor «DELTA»S, EA is ca. 0.4 kcal/mol more bound.; B
0.640011ECDKuhn, Levins, et al., 1968Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.78 ± 0.03EIKuhn, Levins, et al., 1968RDSH

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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


Mass spectrum (electron ionization)

Go To: Top, Condensed 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

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 Japan AIST/NIMC Database- Spectrum MS-NW-6813
NIST MS number 228185

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.

Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Sokolov, L.B., Thermodynamics of the synthesis of isomeric poly(phenylenephthalamides), Vysokomol. Soedin. Ser. B, 1978, 20, 662-666. [all data]

Colomina, Laynez, et al., 1972
Colomina, M.; Laynez, J.L.; Perez-Ossorio, R.; Turrion, C., Enthalpies of combustion and formation of six methyl esters of benzene carboxylic acids, J. Chem. Thermodyn., 1972, 4, 499-506. [all data]

Elliott and Chris, 1968
Elliott, J.H.; Chris, M.D., Some thermodynamic properties of high purity dimethyl terephthalate, J. Chem. Eng. Data, 1968, 13, 475-479. [all data]

Smith and Dole, 1956
Smith, C.W.; Dole, M., Specific heat of synthetic high polymers. VII. Polyethylene terephthalate, J. Polym. Sci., 1956, 20, 37-56. [all data]

Dozen, Fujishima, et al., 1978
Dozen, Y.; Fujishima, S.; Shingu, H., Structures and fusion parameters of methoxycarbonyl-benzenes and -naphthalenes, Thermochim. Acta, 1978, 25, 2, 209, https://doi.org/10.1016/0040-6031(78)85008-4 . [all data]

Elliott and Chris, 1968, 2
Elliott, J.H.; Chris, M.D., Some thermodynamic properties of high purity dimethyl terephthalate, J. Chem. Eng. Data, 1968, 13, 475. [all data]

Smith and Dole, 1956, 2
Smith, C.W.; Dole, M., Specific heat of synthetic high polymers VII. Polyethylene terephthalate, J. Polym. Sci., 1956, 20, 37. [all data]

Shirley and Reedy, 1951
Shirley, D.A.; Reedy, Alkylation with Long Chain p-Toluenesulfonates. III. Reaction of n-Octadecyl p-Toluenesulfonate with p-Tolylmagensium Bromide, J. Am. Chem. Soc., 1951, 73, 4886. [all data]

Hennion and Kurtz, 1943
Hennion, G.F.; Kurtz, R.A., Some Friedel-Crafts Type ALkylations with Boron Trifluoride, J. Am. Chem. Soc., 1943, 65, 1001. [all data]

Roux, Jimenez, et al., 1998
Roux, M.A.; Jimenez, P.; Davalos, J.Z.; Turrion, C.; Afeefy, H.Y.; Liebman, J.F., Enthalpies of formation of methyl benzenecarboxylates, J. Chem. Soc. Faraday Trans., 1998, 94, 887-890. [all data]

Victoria Roux, Jime´nez, et al., 1998
Victoria Roux, María; Jime´nez, Pilar; Dávalos, Juan Z.; Turrión, Concepción; Afeefy, Hussein Y.; Liebman, Joel F., Enthalpies of formation of methyl benzenecarboxylates, Faraday Trans., 1998, 94, 7, 887-890, https://doi.org/10.1039/a800401c . [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]

Kraus, Beranek, et al., 1962
Kraus, M.; Beranek, L.; Kochloeff, K.; Bazant, V., Chem. Prum., 1962, 12, 649. [all data]

Karyakin and Shvetsova, 1982
Karyakin, N.V.; Shvetsova, K.G., Thermodynamics of reactions of 1,4-butanediol with terephthalic acid and its derivatives, Deposited Doc. SPSTL 861 Khp-D82, 1982, 14pp. [all data]

Acree, 1993
Acree, William E., Thermodynamic properties of organic compounds, Thermochimica Acta, 1993, 219, 97-104, https://doi.org/10.1016/0040-6031(93)80486-T . [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]

Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions, Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G . [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Kuhn, Levins, et al., 1968
Kuhn, W.F.; Levins, R.J.; Lilly, A.C., Jr., Electron affinities and ionization potentials of phthalate compounds, J. Chem. Phys., 1968, 49, 5550. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References