Propanenitrile, 2,2-dimethyl-
- Formula: C5H9N
- Molecular weight: 83.1317
- IUPAC Standard InChIKey: JAMNHZBIQDNHMM-UHFFFAOYSA-N
- CAS Registry Number: 630-18-2
- 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: Pivalonitrile; tert-Butyl cyanide; tert-Butylnitrile; Trimethylacetonitrile; 2,2-Dimethylpropionitrile; 2,2-Dimethylpropanenitrile; (CH3)3C-CN; 2-Cyano-2-methylpropane; NSC 890
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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, 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 |
---|---|---|---|---|---|
ΔfH°gas | -0.79 | kcal/mol | Ccr | Hall 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 |
---|---|---|---|---|---|
ΔfH°liquid | -9.53 | kcal/mol | Ccr | Hall and Baldt, 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -768.15 ± 0.17 | kcal/mol | Ccr | Hall and Baldt, 1971 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 55.449 | cal/mol*K | N/A | Westrum and Ribner, 1967 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.64 | 297. | Hall and Baldt, 1971 | DH |
42.870 | 298.15 | Westrum and Ribner, 1967 | T = 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, Chris Muzny 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 |
---|---|---|---|---|---|
Tboil | 370. ± 30. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 288.65 | K | N/A | Butlerov, 1873 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 292.13 | K | N/A | Westrum and Ribner, 1967, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.96 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 8.76 | kcal/mol | V | Hall and Baldt, 1971 | ALS |
ΔvapH° | 8.75 | kcal/mol | N/A | Hall and Baldt, 1971 | DRB |
ΔvapH° | 8.927 ± 0.007 | kcal/mol | V | Howard and Wadso, 1970 | ALS |
ΔvapH° | 9.03 | kcal/mol | I | Westrum and Ribner, 1967 | Based on data from 313. to 371. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.74 | 379.2 | N/A | Majer and Svoboda, 1985 | |
8.72 | 328. | A,I | Stephenson and Malanowski, 1987 | Based on data from 313. to 371. K. See also Westrum and Ribner, 1967.; AC |
8.84 | 318. | BG | Baldt and Hall, 1971 | Based on data from 299. to 365. K.; 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 |
---|---|---|---|---|---|
313.37 to 378.5 | 3.93057 | 1238.154 | -63.416 | Ribner and Westrum, 1967 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.22 | 292.1 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.261 | 213. | Domalski and Hearing, 1996 | CAL |
1.86 | 232.7 | ||
7.60 | 292.1 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0550 | 213. | crystaline, III | crystaline, II | Westrum and Ribner, 1967 | DH |
0.4570 | 232.74 | crystaline, II | crystaline, I | Westrum and Ribner, 1967 | S not equal to H/T, see article.; DH |
2.220 | 292.13 | crystaline, I | liquid | Westrum and Ribner, 1967 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.258 | 213. | crystaline, III | crystaline, II | Westrum and Ribner, 1967 | DH |
1.86 | 232.74 | crystaline, II | crystaline, I | Westrum and Ribner, 1967 | S; DH |
7.598 | 292.13 | crystaline, I | liquid | Westrum and Ribner, 1967 | DH |
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
By formula: Cl- + C5H9N = (Cl- • C5H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.5 ± 1.0 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 11.05 ± 0.20 | kcal/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
By formula: C5H10N+ + C5H9N = (C5H10N+ • C5H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30.2 | kcal/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26.4 | cal/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas 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) | 193.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 186.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.012620 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4N+ | 12.20 | ? | EI | Heerma and deRidder, 1970 | RDSH |
C3H5+ | 13.50 | ? | EI | Heerma and deRidder, 1970 | RDSH |
C4H6N+ | 12.5 | ? | EI | Day, Gowenlock, et al., 1978 | LLK |
C4H6N+ | 12.60 | CH3 | EI | Heerma and deRidder, 1970 | RDSH |
C5H8N+ | 12.05 | H | EI | Heerma and deRidder, 1970 | RDSH |
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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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 |
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, 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
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
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction 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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