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Acetophenone, 4'-amino-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid-182. ± 0.4kJ/molCcbLebedeva, Gutner, et al., 1971Hfusion=3.8±0.1, see Lebedeva, Rjadnenko, et al., 1969
Quantity Value Units Method Reference Comment
Deltacsolid-4252.2 ± 0.4kJ/molCcbLebedeva, Gutner, et al., 1971Hfusion=3.8±0.1, see Lebedeva, Rjadnenko, et al., 1969
Deltacsolid-4726.7 ± 0.8kJ/molCcbSullivan and Hunt, 1949 
Deltacsolid-4729.64 ± 0.84kJ/molCcbSullivan, Kibler, et al., 1948 

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

Quantity Value Units Method Reference Comment
Tboil567.2KN/AWeast and Grasselli, 1989BS
Tboil566. - 568.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus379.KN/ABuckingham and Donaghy, 1982BS
Tfus379.15KN/ACurran and Estok, 1950Uncertainty assigned by TRC = 1. K; TRC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
92.7326.AStephenson and Malanowski, 1987Based on data from 314. - 338. K. See also Aihara, 1960.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
19.6378.2DSCChen, Tang, et al., 2005AC
38.0379.2N/ALebedeva, Ryadnenko, et al., 1971AC

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

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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 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

C8H8NO- + Hydrogen cation = Acetophenone, 4'-amino-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Deltar1470. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1439. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale

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:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
Proton affinity (review)908.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity877.0kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
7.8 ± 0.1PEEgdell, Green, et al., 1975LLK
8.3 ± 0.1EIChin and Harrison, 1969RDSH
8.17 ± 0.02EIFoffani, Pignataro, et al., 1964RDSH
8.27PEGal, Geribaldi, et al., 1985Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H6NO+10.2 ± 0.2CH3EIChin and Harrison, 1969RDSH
C7H6NO+9.34CH3EIBuchs, Rossetti, et al., 1964RDSH

De-protonation reactions

C8H8NO- + Hydrogen cation = Acetophenone, 4'-amino-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Deltar1470. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1439. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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 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-1557
NIST MS number 228486

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.


UV/Visible spectrum

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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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Grammaticakis, 1953
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 966
Instrument n.i.g.
Melting point 106
Boiling point 294; 195(15)

Gas Chromatography

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryHP-11440.Rowland, Blackman, et al., 199525. m/0.25 mm/0.25 «mu»m; Program: 30 0C (4 min) 6 K/min -> 200 0C 15 K/min -> 250 0C (20 min)

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M2181.Vinogradov, 2004Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lebedeva, Gutner, et al., 1971
Lebedeva, N.D.; Gutner, N.M.; Ryadnenko, V.L., Heats of combustion and formation of certain aromatic amino-derivatives, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 561-562. [all data]

Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M., Heats of formation of some N-containing organic compounds, Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]

Sullivan and Hunt, 1949
Sullivan, M.V.; Hunt, H., Heats of combustion. IV. The heats of combustion of five aromatic amines, J. Phys. Chem., 1949, 53, 497-500. [all data]

Sullivan, Kibler, et al., 1948
Sullivan, M.V.; Kibler, G.M.; Hunt, H., Heats of combustion of nitrogen containing compounds, Rpt. Tech. Memo. PUR-3 for USN Project SQUID Contract N6ori-104, Task Order No. 1 Designation No. NR 22 042 by Purdue University, Lafayette, IN, 1948, 1-46. [all data]

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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Curran and Estok, 1950
Curran, B.C.; Estok, G.K., The Stabilization of Highly Polar Resonacne Structures by Hydrogen Bonding I. Electric Moments, J. Am. Chem. Soc., 1950, 72, 4575. [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]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides, Bull. Chem. Soc. Jpn., 1960, 33, 9, 1188-1194, https://doi.org/10.1246/bcsj.33.1188 . [all data]

Chen, Tang, et al., 2005
Chen, Yan-Ping; Tang, Muoi; Kuo, Ju-Chia, Solid--liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone, Fluid Phase Equilibria, 2005, 232, 1-2, 182-188, https://doi.org/10.1016/j.fluid.2005.03.023 . [all data]

Lebedeva, Ryadnenko, et al., 1971
Lebedeva, N.D.; Ryadnenko, V.L.; Kuznetsova, I.N., Heats of combustion and enthalpies of formation of certain aromatic nitro-derivatives, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 549. [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [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]

Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R., Photoelectron spectra of substituted benzenes, Chem. Phys. Lett., 1975, 33, 600. [all data]

Chin and Harrison, 1969
Chin, M.S.; Harrison, A.G., Substituent effects on ion abundances and energetics in substituted acetophenones, Org. Mass Spectrom., 1969, 2, 1073. [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Buchs, Rossetti, et al., 1964
Buchs, A.; Rossetti, G.P.; Susz, B.P., Etude, en fonction de la constante «sigma»p de Hammett, du spectre de masse d'acetophenones p-substituees, Helv. Chim. Acta, 1964, 47, 1563. [all data]

Grammaticakis, 1953
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'ultra-violet moyen et le visible des arylamines isomeres et leurs derives N substitues (3e memoire), Bull. Soc. Chim. Fr., 1953, 20, 93-99. [all data]

Rowland, Blackman, et al., 1995
Rowland, C.Y.; Blackman, A.J.; D'Arcy, B.R.; Rintoul, G.B., Comparison of organic extractives found in leatherwood (Eucryphia lucida) honey and leatherwood flowers and leaves, J. Agric. Food Chem., 1995, 43, 3, 753-763, https://doi.org/10.1021/jf00051a036 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]


Notes

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