Propiolonitrile
- Formula: C3HN
- Molecular weight: 51.0467
- IUPAC Standard InChIKey: LNDJVIYUJOJFSO-UHFFFAOYSA-N
- CAS Registry Number: 1070-71-9
- 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: Cyanoacetylene; HC≡CCN; Cyanaethylene; Cyanoethyne; Propynenitrile; 2-Propynenitrile
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Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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 | 354. | kJ/mol | Ion | Harland, 1986 | Appearance potential |
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 by: Robert L. Brown and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 315.7 | K | N/A | Weast and Grasselli, 1989 |
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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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: CH6N+ + C3HN = (CH6N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | N/A | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
48.5 | 500. | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+; M |
C3N- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1467. ± 8.8 | kJ/mol | G+TS | Taft, Abboud, et al., 1988 | gas phase; B |
ΔrH° | 1439. ± 15. | kJ/mol | EIAE | Graupner, Merrigan, et al., 2006 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1435. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; B |
(CAS Reg. No. 36259-97-9 • 4294967295) +
= CAS Reg. No. 36259-97-9
By formula: (CAS Reg. No. 36259-97-9 • 4294967295C3HN) + C3HN = CAS Reg. No. 36259-97-9
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 319. ± 13. | kJ/mol | N/A | Bartmess, 1980 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: H4N+ + C3HN = (H4N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 95.8 | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
By formula: C3H2N+ + C3HN = (C3H2N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 108. | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; M |
+
= C23H17NO
By formula: C3HN + C20H14O = C23H17NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -117. | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Nonaquous; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
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
L - 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
View reactions leading to C3HN+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.62 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 751.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 720.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.040 ± 0.050 | LPES | Goebbert, Khuseynov, et al., 2010 | Stated electron affinity is the Vertical Detachment Energy; B |
2.56 ± 0.22 | R-A | Heni and Illenberger, 1986 | From CH2=CHCN. Isomer? G3MP2B3 calculations indicate an EA of ca. 0.05 eV; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.56 ± 0.04 | EI | Harland, 1986, 2 | LBLHLM |
11.64 ± 0.01 | PI | Okabe and Dibeler, 1973 | LLK |
11.6 | S | Narayan, 1972 | LLK |
11.60 ± 0.01 | PE | Baker and Turner, 1968 | RDSH |
11.6 ± 0.2 | EI | Dibeler, Reese, et al., 1961 | RDSH |
11.75 | PE | Asbrink, Von Niessen, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH+ | 21.9 ± 0.3 | ? | EI | Dibeler, Reese, et al., 1961 | RDSH |
CN+ | 19.96 ± 0.08 | C2H | EI | Harland, 1986, 2 | LBLHLM |
CN+ | 19.8 ± 0.2 | C2H | EI | Dibeler, Reese, et al., 1961 | RDSH |
C2+ | 18.6 ± 0.2 | ? | EI | Dibeler, Reese, et al., 1961 | RDSH |
C2H+ | 18.84 ± 0.08 | CN | EI | Harland, 1986, 2 | LBLHLM |
C2H+ | 18.19 ± 0.04 | CN | PI | Okabe and Dibeler, 1973 | LLK |
C2H+ | 19.0 ± 0.2 | CN | EI | Dibeler, Reese, et al., 1961 | RDSH |
C2N+ | 18.0 ± 0.5 | CH | EI | Dibeler, Reese, et al., 1961 | RDSH |
C3+ | 24.5 ± 0.5 | ? | EI | Dibeler, Reese, et al., 1961 | RDSH |
C3H+ | 17.76 ± 0.08 | N | EI | Harland, 1986, 2 | LBLHLM |
C3H+ | 18.0 ± 0.2 | N | EI | Dibeler, Reese, et al., 1961 | RDSH |
C3N+ | 17.78 ± 0.08 | H | EI | Harland, 1986, 2 | LBLHLM |
C3N+ | 18.2 ± 0.3 | H | EI | Dibeler, Reese, et al., 1961 | RDSH |
De-protonation reactions
C3N- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1467. ± 8.8 | kJ/mol | G+TS | Taft, Abboud, et al., 1988 | gas phase; B |
ΔrH° | 1439. ± 15. | kJ/mol | EIAE | Graupner, Merrigan, et al., 2006 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1435. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; B |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: CH6N+ + C3HN = (CH6N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+ |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | N/A | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+ |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
48.5 | 500. | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase; Entropy change calculated or estimated, CD3NH3+ |
By formula: C3H2N+ + C3HN = (C3H2N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 108. | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
By formula: H4N+ + C3HN = (H4N+ • C3HN)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 95.8 | kJ/mol | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.6 | J/mol*K | PHPMS | Speller and Meot-Ner (Mautner), 1985 | gas phase |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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
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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118857 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Harland, 1986
Harland, P.W.,
Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "Monochromatic" electron impact,
Int. J. Mass Spectrom. Ion Processes, 1986, 70, 231-236. [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]
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]
Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G.,
Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand,
J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023
. [all data]
Graupner, Merrigan, et al., 2006
Graupner, K.; Merrigan, T.L.; Field, T.A.; Youngs, T.G.A.; Marr, P.C.,
Dissociative Electron Attachment to HCCCN,
New J. Phys., 2006, , 117 (2006), 7, 117, https://doi.org/10.1088/1367-2630/8/7/117
. [all data]
Bartmess, 1980
Bartmess, J.E.,
Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition,
J. Am. Chem. Soc., 1980, 102, 2483. [all data]
Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I.,
Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles,
Zh. Org. Khim., 1983, 19, 1431-1435. [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]
Goebbert, Khuseynov, et al., 2010
Goebbert, D.J.; Khuseynov, D.; Sanov, A.,
Photoelectron Imiaging Spectrum of Cyanovinylidene and Cyanoacetylene anion,
J. Phys. Chem. A, 2010, 114, 6, 2259, https://doi.org/10.1021/jp9106102
. [all data]
Heni and Illenberger, 1986
Heni, M.; Illenberger, E.,
Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN),
Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]
Harland, 1986, 2
Harland, P.W.,
Appearance energies and enthalpies of formation from ionization of cyanoacetylene by "monochromatic" electron impact,
Int. J. Mass Spectrom. Ion Phys., 1986, 70, 231. [all data]
Okabe and Dibeler, 1973
Okabe, H.; Dibeler, V.H.,
Photon impact studies of C2HCN and CH3CN in the vacuum ultraviolet; heats of formation of C2H and CH3CN,
J. Chem. Phys., 1973, 59, 2430. [all data]
Narayan, 1972
Narayan, B.,
Spectra and ionization potential of cyanoacetylene,
Proc. Indian Acad. Sci. Sect. A, 1972, 75, 92. [all data]
Baker and Turner, 1968
Baker, C.; Turner, D.W.,
High resolution molecular photoelectron spectroscopy. III.Acetylenes and azaacetylenes,
Proc. Roy. Soc. (London), 1968, A308, 19. [all data]
Dibeler, Reese, et al., 1961
Dibeler, V.H.; Reese, R.M.; Franklin, J.L.,
Mass spectrometric study of cyanogen and cyanoacetylenes,
J. Am. Chem. Soc., 1961, 83, 1813. [all data]
Asbrink, Von Niessen, et al., 1980
Asbrink, L.; Von Niessen, W.; Bieri, G.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1980, 21, 93. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature Tboil Boiling point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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