1,5-Naphthalenediamine

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

  
• IUPAC Standard InChIKey: KQSABULTKYLFEV-UHFFFAOYSA-N Copy
• CAS Registry Number: 2243-62-1
• 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: 1,5-Diaminonaphthalene; 1,5-Naphthylenediamine; NCI-C03021
• 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
  • IR Spectrum
  • 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

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 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)

Ionization energy determinations

De-protonation reactions

 +  =

By formula: C₁₀H₉N₂^- + H⁺ = C₁₀H₁₀N₂

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: Coblentz Society, Inc.

Condensed Phase Spectrum

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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

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.

Pushin and Sladovic, 1928
Pushin, N.A.; Sladovic, L., Equilibrium in the binary systems cresols-amines, J. Chem. Soc., 1928, 1928, 2474. [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]

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]

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, IR Spectrum, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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