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A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine

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Abstract

The title compound, (E)-1-(2,6-diisopropylphenyl)-2-phenyldiazine (I), was synthesized and characterized using a combination of 1H, 13C, and 15N NMR spectroscopy, infrared and UV/Vis spectroscopy, X-ray crystallography, and GC mass spectrometry. The solid-state structure is also reported. The unsymmetric azobenzene crystallizes in the space group P21/c with unit cell parameters a = 8.001(7) Å, b = 17.827(16) Å, c = 11.129(10) Å, β = 101.960(10)°, V = 1553(2) Å3, Z = 4, D calc = 1.139 g/cm3.

Graphical Abstract

The synthesis of (E)-1-(2,6-diisopropylphenyl)-2-phenyldiazine (I) and its characterization using a combination of combination of 1H, 15N, and 13C NMR spectroscopy, infrared and UV/Vis spectroscopy, mass spectrometry, and X-ray crystallography is described in this report.

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Acknowledgements

For financial support of this work, we acknowledge the U.S. Department of Energy through the Los Alamos G. T. Seaborg Institute for Transactinium Science (Postdoctoral Fellowships to D.O.B. and K.A.E.) and the LANL LDRD Program. The authors gratefully acknowledge M. Teshima (LANL) for mass spectral data and analysis. Los Alamos National Laboratory is operated by Los Alamos National Security, LLC, for the National Nuclear Security Administration of U.S. Department of Energy (contract DE-AC52-06NA25396).

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  1. Los Alamos National Laboratory, Mail Stop J514, Los Alamos, NM, 87545, USA

    David O. Baumann, Karla A. Erickson, Brian L. Scott, Ryszard Michalczyk, L. A. Silks & Jaqueline L. Kiplinger

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  1. David O. Baumann
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  2. Karla A. Erickson
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  3. Brian L. Scott
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  6. Jaqueline L. Kiplinger
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Correspondence to L. A. Silks or Jaqueline L. Kiplinger.

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Baumann, D.O., Erickson, K.A., Scott, B.L. et al. A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine. J Chem Crystallogr 47, 245–248 (2017). https://doi.org/10.1007/s10870-017-0700-4

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  • DOI: https://doi.org/10.1007/s10870-017-0700-4

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