1,8-Naphthalenediamine

• Formula: C₁₀H₁₀N₂
• Molecular weight: 158.1998
• IUPAC Standard InChI: InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2 Copy

  
• IUPAC Standard InChIKey: YFOOEYJGMMJJLS-UHFFFAOYSA-N Copy
• CAS Registry Number: 479-27-6
• 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: Naphthalene-1,8-diamine; 1,8-Diaminonaphthalene; 1,8-Naphthylenediamine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
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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
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₁₀H₁₀N₂⁺ (ion structure unspecified)

Appearance energy determinations

De-protonation reactions

C₁₀H₉N₂^- +  =

By formula: C₁₀H₉N₂^- + H⁺ = C₁₀H₁₀N₂

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

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

Verevkin, Georgieva, et al., 2007
Verevkin, Sergey P.; Georgieva, Miglena; Melkhanova, Svetlana V., Vapor Pressures and Phase Transitions of a Series of the Aminonaphthalenes, J. Chem. Eng. Data, 2007, 52, 1, 286-290, https://doi.org/10.1021/je060394v . [all data]

Ribeiro da Silva, Lobo Ferreira, et al., 2010
Ribeiro da Silva, Manuel A.V.; Lobo Ferreira, Ana I.M.C.; Santos, Ana Filipa L.O.M.; Ferreira, Cristiana M.A.; Barros, Delfina C.B.; Reis, Joana A.C.; Costa, José C.S.; Calvinho, Maria Miguel G.; Rocha, Sónia I.A.; Pinto, Sónia P.; Freire, Sónia S.L.; Almeida, Suzete M.; Guimarães, Vanessa S.; Almeida, Vasco N.M., Enthalpies of combustion, vapour pressures, and enthalpies of sublimation of the 1,5- and 1,8-diaminonaphthalenes, The Journal of Chemical Thermodynamics, 2010, 42, 3, 371-379, https://doi.org/10.1016/j.jct.2009.09.009 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Maier, 1974
Maier, J.P., Photoelectron spectroscopy of peri- amino naphthalenes, Helv. Chim. Acta, 1974, 57, 994. [all data]

Arnett, Venkatasubaramanian, et al., 1982
Arnett, E.M.; Venkatasubaramanian, K.G.; McIver, R.T.; Fukuda, E.K.; Bordwell, F.G.; Press, F.D., Stabilization of the monoanion of 1,8-diaminonaphthalene by intramolecular hydrogen bonding. A novel case of anion homoconjugation in superbase solution, J. Am. Chem. Soc., 1982, 104, 325. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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