1,5-Naphthalenediamine

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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 by: John E. Bartmess

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Individual Reactions

1,5-diaminonaphthalenide anion + Hydrogen cation = 1,5-Naphthalenediamine

By formula: C10H9N2- + H+ = C10H10N2

Quantity Value Units Method Reference Comment
Δr356.9 ± 2.1kcal/molG+TSArnett, Venkatasubaramanian, et al., 1982gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr349.6 ± 2.0kcal/molIMREArnett, Venkatasubaramanian, et al., 1982gas phase; value altered from reference due to change in acidity scale

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

IE (eV) Method Reference Comment
6.74 ± 0.02PEMaier, 1974LLK

De-protonation reactions

1,5-diaminonaphthalenide anion + Hydrogen cation = 1,5-Naphthalenediamine

By formula: C10H9N2- + H+ = C10H10N2

Quantity Value Units Method Reference Comment
Δr356.9 ± 2.1kcal/molG+TSArnett, Venkatasubaramanian, et al., 1982gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr349.6 ± 2.0kcal/molIMREArnett, Venkatasubaramanian, et al., 1982gas phase; value altered from reference due to change in acidity scale; B

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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IR 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

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Owner COBLENTZ SOCIETY
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin TENNESSEE EASTMAN COMPANY, RESEARCH LABORATORIES
Source reference COBLENTZ NO. 309
Date Not specified, most likely prior to 1970
Name(s) 1,5-naphthalenediamine
State SOLID (KBr PELLET)
Instrument Not specified, most likely a prism, grating, or hybrid spectrometer.
Resolution 4
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY NIST FROM HARD COPY

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


Mass spectrum (electron ionization)

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

Spectrum

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Mass spectrum
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Additional Data

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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, 1998.
NIST MS number 291224

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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.

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]

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


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References