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
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Phase change data

Go To: Top, Gas phase ion energetics 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 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

Go To: Top, Phase change 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 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

Mass spectrum (electron ionization)

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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

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

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, Mass spectrum (electron ionization), 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.