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Urethane

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-106.7kcal/molCmBernard, Boukari, et al., 1976hfusion=20.9±0.8 kJ/mol

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
Deltafliquid-118.9kcal/molCmBernard, Boukari, et al., 1976hfusion=20.9±0.8 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltafsolid-123.6kcal/molCcbSchmidt and Becker, 1933ALS
Quantity Value Units Method Reference Comment
Deltacsolid-397.65kcal/molCcbSchmidt and Becker, 1933ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
37.388300.DeWit, DeKruif, et al., 1983T = 90 to 330 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil456.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil458.40KN/ALecat, 1947Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Tfus322. ± 4.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple321.41KN/ADe Wit, De Kruif, et al., 1983Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Deltavap12. ± 0.60kcal/molVBernard, Boukari, et al., 1976hfusion=20.9±0.8 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltasub18.2kcal/molN/ADe Wit, Van Miltenburg, et al., 1983AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
13.5353.AStephenson and Malanowski, 1987Based on data from 338. - 457. K. See also Stull, 1947.; 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
339.0 - 457.5.483472278.15-41.707Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
18.6265.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 256. - 273. K.; AC
17.2322.N/ABernard, Boukari, et al., 1976AC
21.3 ± 0.2299.GSDavies and Jones, 1959Based on data from 292. - 307. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
4.0139321.41DeWit, DeKruif, et al., 1983DH
4.9952321.7Bernard, Boukari, et al., 1976DH
3.640321.9Acree, 1991AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.49321.41DeWit, DeKruif, et al., 1983DH
15.5321.7Bernard, Boukari, et al., 1976DH

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:


Reaction thermochemistry data

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C3H6NO2- + Hydrogen cation = Urethane

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Deltar361.9 ± 2.3kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar354.9 ± 2.2kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
10.2PEOverman, Taylor, et al., 1978LLK
10.62PEOverman, Taylor, et al., 1978Vertical value; LLK

De-protonation reactions

C3H6NO2- + Hydrogen cation = Urethane

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Deltar361.9 ± 2.3kcal/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar354.9 ± 2.2kcal/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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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Mass 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-1668
NIST MS number 227700

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Bernard, Boukari, et al., 1976
Bernard, M.A.; Boukari, Y.; Busnot, F., Thermodynamic study of methyl and ethyl carbamates and their eutectic, Thermochim. Acta, 1976, 16, 267-275. [all data]

Schmidt and Becker, 1933
Schmidt, V.A.; Becker, F., Die Bildungswarme von Nitrocellulofen, Nitroglycerin und anderen widuigen Beltandteilen von Treibmitteln, Z. Gesamte Schiess Sprengstoffwes., 1933, 33, 280-282. [all data]

DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodynam., 1983, 15, 891-902. [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]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

De Wit, De Kruif, et al., 1983
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem. Thermodyn., 1983, 15, 9, 891, https://doi.org/10.1016/0021-9614(83)90095-2 . [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [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]

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]

Davies and Jones, 1959
Davies, Mansel; Jones, A. Hamilton, Lattice energies of some n-methyl amides and of some carbamates, Trans. Faraday Soc., 1959, 55, 1329, https://doi.org/10.1039/tf9595501329 . [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Overman, Taylor, et al., 1978
Overman, L.E.; Taylor, G.F.; Houk, K.N.; Domelsmith, L.N., Diels-Alder reactions between trans-1-N-acylamino-1,3-dienes and methyl acrylate. A correlation between diene photoelectron ionization potentials and reactivity, stereoselectivity, and regioselectivity, J. Am. Chem. Soc., 1978, 100, 3182. [all data]


Notes

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