Morpholine

• Formula: C₄H₉NO
• Molecular weight: 87.1204
• IUPAC Standard InChI: InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2 Copy

  
• IUPAC Standard InChIKey: YNAVUWVOSKDBBP-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-91-8
• 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: p-Isoxazine, tetrahydro-; BASF 238; Diethylene Imidoxide; Diethylene oximide; Diethylenimide oxide; Tetrahydro-p-oxazine; Tetrahydro-1,4-oxazine; Tetrahydro-2H-1,4-oxazine; 1-Oxa-4-azacyclohexane; 2H-1,4-Oxazine, tetrahydro-; 4H-1,4-Oxazine, tetrahydro-; Diethyleneimide oxide; Tetrahydro-1,4-isoxazine; Drewamine; NA 2054; UN 2054; NSC 9376
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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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

Constant pressure heat capacity of liquid

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:
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

Enthalpy of vaporization

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

Go To: Top, Condensed phase thermochemistry data, 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.

Gutner, Masalitinova, et al., 1982
Gutner, N.M.; Masalitinova, T.N.; Mon'yakova, O.N.; Lebedeva, N.D., Heats of combustion and formation of some cyclic compounds, Termodin. Organ. Soedin., 1982, 46-49. [all data]

Lyashkov, 1980
Lyashkov, V.I., Thermal characteristics of morpholine, Izv. Vyssh. Uchebn., Khim. Khim. Tekhnol., 1980, 23, 1085-1086. [all data]

Trimble, Engle, et al., 1942
Trimble, H.M.; Engle, C.J.; Brown, R.A.; Schmuck, R.F., The specific heats of morpholine and its aqueous solutions, J. Am. Chem. Soc., 1942, 64, 679-681. [all data]

Vedal, Ellestad, et al., 1976
Vedal, D.; Ellestad, O.H.; Klaeboe, P.; Hagen, G., The vibrational spectra of piperidine and morpholine and their N-deuterated analogs, spectrochim. Acta, Part A, 1976, 32, 877. [all data]

Anonymous, 1955
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Dermer and Dermer, 1937
Dermer, V.H.; Dermer, O.C., Physical constants of morpholine., J. Am. Chem. Soc., 1937, 59, 1148. [all data]

Rojas-Aguilar, Ginez-Carbajal, et al., 2005
Rojas-Aguilar, A.; Ginez-Carbajal, F.; Orozco-Guareno, E.; Flores-Segura, H., Measurement of enthalpies of vaporization of volatile heterocyclic compounds by DSC, J Therm Anal Calorim, 2005, 79, 1, 95-100, https://doi.org/10.1007/s10973-004-0568-3 . [all data]

Verevkin, 1998
Verevkin, Sergey P., Thermochemistry of amines: strain in six-membered rings from experimental standard molar enthalpies of formation of morpholines and piperazines, The Journal of Chemical Thermodynamics, 1998, 30, 9, 1069-1079, https://doi.org/10.1006/jcht.1998.0371 . [all data]

Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib, Thermogravimetric determination of the heat of vaporization of some highly polar solvents, J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302 . [all data]

Wu, Locke, et al., 1991
Wu, Huey S.; Locke, William E.; Sandler, Stanley I., Isothermal vapor-liquid equilibrium of binary mixtures containing morpholine, J. Chem. Eng. Data, 1991, 36, 1, 127-130, https://doi.org/10.1021/je00001a037 . [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]

Cabani, Conti, et al., 1975
Cabani, Sergio; Conti, G.; Giannessi, D.; Lepori, L., Thermodynamic study of aqueous dilute solutions of organic compounds. Part 3.---Morpholines and piperazines, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 1154, https://doi.org/10.1039/f19757101154 . [all data]

Palczewska-Tulinska, Cholinski, et al., 1983
Palczewska-Tulinska, Marcela; Cholinski, Jacek; Szafranski, Andrzej; Wyrzykowska-Stankiewicz, Danuta, Maximum-likelihood evaluation of antoine equation constants for vapor pressures of morpholine, n-heptane, cyclohexane and methylcyclohexane, Fluid Phase Equilibria, 1983, 11, 3, 233-243, https://doi.org/10.1016/0378-3812(83)85026-2 . [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]

Domelsmith and Houk, 1977
Domelsmith, L.N.; Houk, K.N., Photoelectron spectra of cyclopentanone and cyclohexanone enamines, Tetrahedron Lett., 1977, 23, 1981. [all data]

Colonna, Distefano, et al., 1975
Colonna, F.P.; Distefano, G.; Pignataro, S.; Pitacco, G.; Valentin, E., Ionization energies of some amines and enamines and an estimation of their relative basicity in gaseous phase, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1572. [all data]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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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