Hexanenitrile
- Formula: C6H11N
- Molecular weight: 97.1582
- IUPAC Standard InChIKey: AILKHAQXUAOOFU-UHFFFAOYSA-N
- CAS Registry Number: 628-73-9
- 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: Capronitrile; Hexanonitrile; Pentyl cyanide; Tricapronile; 1-Cyanopentane; n-Amyl cyanide; n-Caproic nitrile; n-Capronitrile; n-Pentyl cyanide; NSC 1076
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Phase change data
Go To: Top, 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 435. ± 5. | K | AVG | N/A | Average of 17 out of 18 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 184.15 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 192.84 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 193.75 | K | N/A | Simon, 1929 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 228.15 | K | N/A | Jaeger and Kahn, 1915 | TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 633.8 | K | N/A | Castillo-Lopez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.2 K; Visual, TE with digital voltmeter cal. by meas. on alkanes.; TRC |
Tc | 621.8 | K | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 2.5 K; TRC |
Tc | 622.05 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 621.75 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 32.2 ± 0.3 | atm | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.45 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 11.45 ± 0.024 | kcal/mol | V | Howard and Wadso, 1970 | ALS |
ΔvapH° | 11.4 ± 0.02 | kcal/mol | C | Howard, Wadsö, et al., 1970 | AC |
ΔvapH° | 11.7 | kcal/mol | EB | Dreisbach and Shrader, 1949 | Based on data from 365. to 437. K. See also Dreisbach and Martin, 1949, 2 and Emel'yanenko, Verevkin, et al., 2005.; AC |
ΔvapH° | 11.4 ± 0.02 | kcal/mol | MM | Heim, 1933 | Based on data from 293. to 452. K. See also Emel'yanenko, Verevkin, et al., 2005.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.3 | 386. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 371. to 442. K. See also Meyer and Hotz, 1973.; AC |
10.7 | 359. | EB | Meyer, Renner, et al., 1971 | Based on data from 344. to 441. 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 |
---|---|---|---|---|---|
371.23 to 441.66 | 4.1904 ± 0.0013 | 1553.81 ± 0.89 | -65.811 ± 0.097 | Meyer and Hotz, 1973 | |
365.13 to 436.80 | 4.10248 | 1502.715 | -70.588 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change 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 as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
192.3 | Cao and Holmes, 1999 | MM |
193. | Cao and Holmes, 1999 | MM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H10N+ | 12.62 | H | EI | Heerma, deRidder, et al., 1969 | RDSH |
IR Spectrum
Go To: Top, Phase change data, Gas phase ion energetics data, 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: Coblentz Society, Inc.
Condensed Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | WYANDOTTE CHEMICALS CORP., WYANDOTTE, MICHIGAN, USA |
Source reference | COBLENTZ NO. 3771 |
Date | Not specified, most likely prior to 1970 |
State | LIQUID |
Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
Path length | 0.005 CM |
Resolution | 4 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY |
Boiling point | 160-162.5 C |
References
Go To: Top, Phase change 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.
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [all data]
Simon, 1929
Simon, I.,
Freezing Temperature of Organic Compounds. XI. Compounds in C5 and C6.,
Bull. Soc. Chim. Belg., 1929, 38, 47-70. [all data]
Jaeger and Kahn, 1915
Jaeger, F.M.; Kahn, J.,
The temperature-coefficients of the free molecular surface energy of liquids between -80!31 and 1650!31: x measurements relating to a series of aliphatic compounds,
J. Chem. Soc., 1915, 108, 747-48. [all data]
Castillo-Lopez and Trejo Rodriguez, 1987
Castillo-Lopez, N.; Trejo Rodriguez, A.,
The critical temperatures and pressures of several n-alkanenitriles,
J. Chem. Thermodyn., 1987, 19, 671. [all data]
Guye and Mallet, 1902
Guye, P.A.; Mallet, E.,
Critical Constant and Molecular Complexity of Several Organic Compds.,
C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]
Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E.,
Measurement of Critical Constants,
Arch. Sci. Phys. Nat., 1902, 13, 274-296. [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]
Howard, Wadsö, et al., 1970
Howard, Peter B.; Wadsö, Ingemar; Nyborg, Jens; Ragnarsson, Ulf; Rasmussen, S.E.; Sunde, Erling; Sørensen, Nils Andreas,
Enthalpies of Vaporization of Organic Compounds. IV. Alkyl Nitriles.,
Acta Chem. Scand., 1970, 24, 145-149, https://doi.org/10.3891/acta.chem.scand.24-0145
. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Dreisbach and Martin, 1949, 2
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053
. [all data]
Emel'yanenko, Verevkin, et al., 2005
Emel'yanenko, Vladimir N.; Verevkin, Sergey P.; Koutek, Bohumir; Doubsky, Jan,
Vapour pressures and enthalpies of vapourization of a series of the linear aliphatic nitriles,
The Journal of Chemical Thermodynamics, 2005, 37, 1, 73-81, https://doi.org/10.1016/j.jct.2004.08.004
. [all data]
Heim, 1933
Heim, G.,
Bull. Soc. Chim. Belg., 1933, 42, 467. [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]
Meyer and Hotz, 1973
Meyer, Edwin F.; Hotz, Roger D.,
High-precision vapor-pressure data for eight organic compounds,
J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008
. [all data]
Meyer, Renner, et al., 1971
Meyer, Edwin F.; Renner, Terrence A.; Stec, Kenneth S.,
Cohesive energies in polar organic liquids. II. n-Alkane nitriles and the 1-chloro alkanes,
J. Phys. Chem., 1971, 75, 5, 642-648, https://doi.org/10.1021/j100675a008
. [all data]
Cao and Holmes, 1999
Cao, J.; Holmes, J.L.,
Determining the proton affinities of nitriles by the kinetic method,
European J. Mass Spectrometry, 1999, 5, 19-22. [all data]
Heerma, deRidder, et al., 1969
Heerma, W.; deRidder, J.J.; Dijkstra, G.,
The electron-impact-induced fragmentation of n-alkyl cyanides,
Org. Mass Spectrom., 1969, 2, 1103. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point 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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