Dicyandiamide

• Formula: C₂H₄N₄
• Molecular weight: 84.0800
• IUPAC Standard InChI: InChI=1S/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6) Copy

  
• IUPAC Standard InChIKey: QGBSISYHAICWAH-UHFFFAOYSA-N Copy
• CAS Registry Number: 461-58-5
• 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: Guanidine, cyano-; Cyanoguanidine; Dicyanodiamide; N-Cyanoguanidine; Pyroset DO; 1-Cyanoguanidine; 2-Cyanoguanidine; Guanidine-1-carbonitrile; NCN=C(NH2)2; Dicyanediamide; Dicyandiamin; ACR-H 3636; Araldite HT 986; Araldite XB 2879B; Araldite XB 2979B; Bakelite VE 2560; Epicure DICY 15; Epicure DICY 7; Guanidine, N-cyano-; NSC 2031; XB 2879B
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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: William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

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 compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₂H₄N₄⁺ (ion structure unspecified)

Ionization energy determinations

References

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

Medard and Thomas, 1952
Medard, L.; Thomas, M., Determination des chaleurs de combustion de douze composes organiques utilises dans les poudres et enplosies, Mem. Poudres, 1952, 34, 421-442. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Salley and Gray, 1951
Salley, D.J.; Gray, J.B., Heats of combustion of some organic nitrogen compounds, J. Am. Chem. Soc., 1951, 73, 5925. [all data]

Salley and Gray, 1948
Salley, D.J.; Gray, J.B., Heats of combustion of some organic nitrogen compounds, J. Am. Chem. Soc., 1948, 70, 2650-2653. [all data]

Handrick, 1956
Handrick, G.R., Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]

Stephenson and Berets, 1952
Stephenson, C.C.; Berets, D.J., The heat capacities and entropies of melamine and dicyandiamide, J. Am. Chem. Soc., 1952, 74, 882-883. [all data]

David, 1964
David, D.J., Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters, Anal. Chem., 1964, 36, 2162-2166. [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Zhang, Tan, et al., 1997
Zhang, Ji-Biao; Tan, Zhi-Cheng; Meng, Shuang-He; Li, Shao-Hui; Zhang, Li-Ming, Heat capacity and thermal decomposition of dicyandiamide, Thermochimica Acta, 1997, 307, 1, 11-15, https://doi.org/10.1016/S0040-6031(97)00323-7 . [all data]

Klasinc, Butkovic, et al., 1980
Klasinc, L.; Butkovic, V.; Novak, I.; Mihalic, M.; Toso, R.; Sunjic, V., Application of photoelectron spectroscopy to biologically active molecules and their constituent parts. VII. N-cyanoazomethines, Gazz. Chim. Ital., 1980, 110, 287. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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