1,4-Benzenedicarboxylic acid, dimethyl ester
- Formula: C10H10O4
- Molecular weight: 194.1840
- IUPAC Standard InChIKey: WOZVHXUHUFLZGK-UHFFFAOYSA-N
- CAS Registry Number: 120-61-6
- 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: Terephthalic acid, dimethyl ester; Dimethyl p-phthalate; Dimethyl terephthalate; Dimethyl 1,4-benzenedicarboxylate; Methyl 4-(carbomethoxy)benzoate; Dimethyl p-benzenedicarboxylate; Dimethylester kyseliny isoftalove; DMT; NCI-C50055; Dimethylester kyseliny tereftalove; Dimethyl ester of 1,4-benzenedicarboxylic acid; Terephthalate, dimethyl; 1,4-Benzenedicarboxylic acid, 1,4-dimethyl ester; Methyl p-(methoxycarbonyl)benzoate; NSC 3503; Dimethyl terphthalate
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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:
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 |
---|---|---|---|---|---|
Tfus | 415.2 | K | N/A | Dozen, Fujishima, et al., 1978 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 413.80 | K | N/A | Elliott and Chris, 1968 | Uncertainty assigned by TRC = 0.01 K; TRC |
Tfus | 413.8 | K | N/A | Smith and Dole, 1956 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 413. | K | N/A | Shirley and Reedy, 1951 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 413. | K | N/A | Hennion and Kurtz, 1943 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 25.00 ± 0.07 | kcal/mol | C | Roux, Jimenez, et al., 1998 | ALS |
ΔsubH° | 25.00 ± 0.07 | kcal/mol | N/A | Victoria Roux, Jime´nez, et al., 1998 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15. | 428. | A | Stephenson and Malanowski, 1987 | Based on data from 413. to 523. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.81 ± 0.07 | 321. | ME | Victoria Roux, Jime´nez, et al., 1998 | Based on data from 311. to 330. K.; AC |
22.6 | 388. | N/A | Stephenson and Malanowski, 1987 | Based on data from 373. to 413. K.; AC |
21.1 | 393. | GS | Kraus, Beranek, et al., 1962 | Based on data from 373. to 413. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.6482 | 415.4 | Karyakin and Shvetsova, 1982 | DH |
7.5600 | 413.79 | Elliott and Chris, 1968, 2 | DH |
7.6721 | 413.8 | Smith and Dole, 1956, 2 | DH |
7.670 | 413.8 | Acree, 1993 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
18.4 | 415.4 | Karyakin and Shvetsova, 1982 | DH |
18.27 | 413.79 | Elliott and Chris, 1968, 2 | DH |
18.5 | 413.8 | Smith and Dole, 1956, 2 | DH |
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:
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) | 201.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 194.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.824 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K)=-20.2 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
0.824 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
0.640011 | ECD | Kuhn, Levins, et al., 1968 | Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.78 ± 0.03 | EI | Kuhn, Levins, et al., 1968 | RDSH |
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.
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
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
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]
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, 475-479. [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, 37-56. [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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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