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Propanenitrile, 2,2-dimethyl-

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Gas 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
Deltafgas-3.3kJ/molCcrHall and Baldt, 1971 

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-39.9kJ/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3213.9 ± 0.71kJ/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
liquid232.00J/mol*KN/AWestrum and Ribner, 1967DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
153.3297.Hall and Baldt, 1971DH
179.37298.15Westrum and Ribner, 1967T = 5 to 350 K.; 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil370. ± 30.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus288.65KN/AButlerov, 1873Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Ttriple292.13KN/AWestrum and Ribner, 1967, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Deltavap37.5kJ/molN/AMajer and Svoboda, 1985 
Deltavap36.7kJ/molVHall and Baldt, 1971ALS
Deltavap36.6kJ/molN/AHall and Baldt, 1971DRB
Deltavap37.35 ± 0.03kJ/molVHoward and Wadso, 1970ALS
Deltavap37.8kJ/molIWestrum and Ribner, 1967Based on data from 313. - 371. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
32.4379.2N/AMajer and Svoboda, 1985 
36.5328.A,IStephenson and Malanowski, 1987Based on data from 313. - 371. K. See also Westrum and Ribner, 1967.; AC
37.0318.BGBaldt and Hall, 1971Based on data from 299. - 365. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
313.37 - 378.53.936281238.154-63.416Ribner and Westrum, 1967Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
9.29292.1Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
1.09213.Domalski and Hearing, 1996CAL
7.78232.7
31.8292.1

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.230213.crystaline, IIIcrystaline, IIWestrum and Ribner, 1967DH
1.912232.74crystaline, IIcrystaline, IWestrum and Ribner, 1967S not equal to H/T, see article.; DH
9.288292.13crystaline, IliquidWestrum and Ribner, 1967DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.08213.crystaline, IIIcrystaline, IIWestrum and Ribner, 1967DH
7.78232.74crystaline, IIcrystaline, IWestrum and Ribner, 1967S; DH
31.79292.13crystaline, IliquidWestrum and Ribner, 1967DH

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

Chlorine anion + Propanenitrile, 2,2-dimethyl- = (Chlorine anion bullet Propanenitrile, 2,2-dimethyl-)

By formula: Cl- + C5H9N = (Cl- bullet C5H9N)

Quantity Value Units Method Reference Comment
Deltar77.4 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar46.23 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B

C5H10N+ + Propanenitrile, 2,2-dimethyl- = (C5H10N+ bullet Propanenitrile, 2,2-dimethyl-)

By formula: C5H10N+ + C5H9N = (C5H10N+ bullet C5H9N)

Quantity Value Units Method Reference Comment
Deltar126.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M

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

View reactions leading to C5H9N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)810.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity780.2kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Reference Comment
0.012620 ± 0.000087Hammer, Diri, et al., 2003B

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4N+12.20?EIHeerma and deRidder, 1970RDSH
C3H5+13.50?EIHeerma and deRidder, 1970RDSH
C4H6N+12.5?EIDay, Gowenlock, et al., 1978LLK
C4H6N+12.60CH3EIHeerma and deRidder, 1970RDSH
C5H8N+12.05HEIHeerma and deRidder, 1970RDSH

Ion clustering 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C5H10N+ + Propanenitrile, 2,2-dimethyl- = (C5H10N+ bullet Propanenitrile, 2,2-dimethyl-)

By formula: C5H10N+ + C5H9N = (C5H10N+ bullet C5H9N)

Quantity Value Units Method Reference Comment
Deltar126.kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase; M

Chlorine anion + Propanenitrile, 2,2-dimethyl- = (Chlorine anion bullet Propanenitrile, 2,2-dimethyl-)

By formula: Cl- + C5H9N = (Cl- bullet C5H9N)

Quantity Value Units Method Reference Comment
Deltar77.4 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar46.23 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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, Ion clustering data, IR Spectrum, NIST Free Links, 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

View image of digitized spectrum (can be printed in landscape orientation).

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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-6396
NIST MS number 228259

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes

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

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Westrum and Ribner, 1967
Westrum, E.F., Jr.; Ribner, A., Trimethylacetonitrile. Low-temperature heat capacity, vapor pressure, and chemical thermodynamics of the crystalline, liquid, and gaseous phases, J. Phys. Chem., 1967, 71, 1216-1224. [all data]

Butlerov, 1873
Butlerov, A., Justus Liebigs Ann. Chem., 1873, 170, 151. [all data]

Westrum and Ribner, 1967, 2
Westrum, E.F.; Ribner, A., Trimethylacetonitrile low-temperature heat capacity, vapor pressure, and chemical thermodynamics of the crystalline, liquid and gaseous phases, J. Phys. Chem., 1967, 71, 1216. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Howard and Wadso, 1970
Howard, P.B.; Wadso, I., Enthalpies of vaporization of organic compounds IV. Alkyl Nitriles, Acta Chem. Scand., 1970, 24, 145. [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]

Baldt and Hall, 1971
Baldt, J.H.; Hall, H.K.K., Jr., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Ribner and Westrum, 1967
Ribner, A.; Westrum, E.F., Jr., Dimethylmalononitrile. Low-Temperature Heat Capacity, Vapor Pressure, Density, and Chemical Thermodynamics of the Crystalline, Liquid, and Gaseous Phases, J. Phys. Chem., 1967, 71, 5, 1208-1224, https://doi.org/10.1021/j100864a005 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Li, Ross, et al., 1996
Li, C.; Ross, P.; Szulejko, J.; McMahon, T.B., High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase Sn2 Reactions., J. Am. Chem. Soc., 1996, 118, 39, 9360, https://doi.org/10.1021/ja960565o . [all data]

Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites, J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020 . [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]

Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N., Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules, J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959 . [all data]

Heerma and deRidder, 1970
Heerma, W.; deRidder, J.J., The electron-impact induced fragmentation of some alkyl isocyanides and alpha-branched alkyl cyanides, Org. Mass Spectrom., 1970, 3, 1439. [all data]

Day, Gowenlock, et al., 1978
Day, J.S.; Gowenlock, B.G.; Johnson, C.A.F.; McInally, I.D.; Pfab, J., Appearance potential studies of some geminal substituted C-nitroso- compounds, J. Chem. Soc. Perkin Trans. 2, 1978, 10, 1110. [all data]


Notes

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