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

Abstract

We synthesized and characterized the title compound, (E)-1-(2,6-diisopropylphenyl)-2-phenyldiazine (I) 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 P2 1/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) Å 3, Z = 4, D calc = 1.139 g/cm 3.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA)
OSTI Identifier:
1406230
Report Number(s):
LA-UR-17-25868
Journal ID: ISSN 1074-1542
Grant/Contract Number:  
AC52-06NA25396
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Chemical Crystallography
Additional Journal Information:
Journal Volume: 47; Journal Issue: 6; Journal ID: ISSN 1074-1542
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; signle crystal x-ray crystallography; 15N NMR; azobenzene; aniline; nitrosobenzene; mills reaction

Citation Formats

Baumann, David O., Erickson, Karla A., Scott, Brian L., Michalczyk, Ryszard, Silks, III, Louis A., and Kiplinger, Jaqueline L. A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine. United States: N. p., 2017. Web. doi:10.1007/s10870-017-0700-4.
Baumann, David O., Erickson, Karla A., Scott, Brian L., Michalczyk, Ryszard, Silks, III, Louis A., & Kiplinger, Jaqueline L. A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine. United States. doi:10.1007/s10870-017-0700-4.
Baumann, David O., Erickson, Karla A., Scott, Brian L., Michalczyk, Ryszard, Silks, III, Louis A., and Kiplinger, Jaqueline L. Tue . "A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine". United States. doi:10.1007/s10870-017-0700-4. https://www.osti.gov/servlets/purl/1406230.
@article{osti_1406230,
title = {A Sterically Biased Unsymmetrical Azobenzene Derivative: Synthesis, Molecular Structure, and 15N NMR Spectroscopic Analysis of (E)-1-(2,6-Diisopropylphenyl)-2-phenyldiazine},
author = {Baumann, David O. and Erickson, Karla A. and Scott, Brian L. and Michalczyk, Ryszard and Silks, III, Louis A. and Kiplinger, Jaqueline L.},
abstractNote = {We synthesized and characterized the title compound, (E)-1-(2,6-diisopropylphenyl)-2-phenyldiazine (I) 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, Dcalc = 1.139 g/cm3.},
doi = {10.1007/s10870-017-0700-4},
journal = {Journal of Chemical Crystallography},
number = 6,
volume = 47,
place = {United States},
year = {2017},
month = {10}
}

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    Works referencing / citing this record:

    On the 75th anniversary of Prontosil
    journal, March 2011


    Syntheses of new functionalized azobenzenes for potential molecular electronic devices
    journal, October 2006


    Azobenzenes—synthesis and carbohydrate applications
    journal, December 2009


    Elucidating the Mechanism of Uranium Mediated Diazene N═N Bond Cleavage
    journal, November 2016


    Small-Molecule Activation Mediated by a Uranium Bipyridyl Metallocene
    journal, March 2017


    The Photochemical Isomerization of Azobenzene 1
    journal, July 1958

    • Zimmerman, George; Chow, Lue-Yung; Paik, Un-Jin
    • Journal of the American Chemical Society, Vol. 80, Issue 14
    • DOI: 10.1021/ja01547a010

    Multi-Electron Reduction from Alkyl/Hydride Ligand Combinations in U 4+ Complexes
    journal, September 2008

    • Evans, William J.; Montalvo, Elizabeth; Kozimor, Stosh A.
    • Journal of the American Chemical Society, Vol. 130, Issue 37
    • DOI: 10.1021/ja805107v

    Influence of the 5f Orbitals on the Bonding and Reactivity in Organoactinides: Experimental and Computational Studies on a Uranium Metallacyclopropene
    journal, April 2016

    • Zhang, Lei; Hou, Guohua; Zi, Guofu
    • Journal of the American Chemical Society, Vol. 138, Issue 15
    • DOI: 10.1021/jacs.6b01391

    Examining the Effects of Ligand Variation on the Electronic Structure of Uranium Bis(imido) Species
    journal, October 2016

    • Kiernicki, John J.; Ferrier, Maryline G.; Lezama Pacheco, Juan S.
    • Journal of the American Chemical Society, Vol. 138, Issue 42
    • DOI: 10.1021/jacs.6b06989

    Photoisomerization Dynamics and Pathways of trans - and cis -Azobenzene in Solution from Broadband Femtosecond Spectroscopies and Calculations
    journal, July 2014

    • Quick, M.; Dobryakov, A. L.; Gerecke, M.
    • The Journal of Physical Chemistry B, Vol. 118, Issue 29
    • DOI: 10.1021/jp504999f

    Fast Synthesis of Hydrazine and Azo Derivatives by Oxidation of Rare-Earth-Metal−Nitrogen Bonds
    journal, February 2011

    • Zhang, Lijun; Xia, Jing; Li, Qinghai
    • Organometallics, Vol. 30, Issue 3
    • DOI: 10.1021/om1009928

    Reactivity of U 3+ Metallocene Allyl Complexes Leads to a Nanometer-Sized Uranium Carbonate, [(C 5 Me 5 ) 2 U] 6 (μ-κ 12 -CO 3 ) 6
    journal, August 2013

    • Webster, Christopher L.; Ziller, Joseph W.; Evans, William J.
    • Organometallics, Vol. 32, Issue 17
    • DOI: 10.1021/om400526h

    [(C5Me5)2U][(µ-Ph)2BPh2] as a four electron reductant
    journal, January 2005

    • Evans, William J.; Kozimor, Stosh A.; Ziller, Joseph W.
    • Chemical Communications, Issue 37
    • DOI: 10.1039/b508612d

    Synthesis of azobenzenes: the coloured pieces of molecular materials
    journal, January 2011


    Carbon-13 and nitrogen-15 NMR spectra of cis- and trans-azobenzene, 4-monosubstituted and 4,4'-disubstituted trans-azobenzenes
    journal, January 1982

    • Lyčka, Antonín
    • Collection of Czechoslovak Chemical Communications, Vol. 47, Issue 4
    • DOI: 10.1135/cccc19821112

    Azo dyes: past, present and the future
    journal, December 2011

    • Bafana, Amit; Devi, Sivanesan Saravana; Chakrabarti, Tapan
    • Environmental Reviews, Vol. 19, Issue NA
    • DOI: 10.1139/a11-018

    NMR nomenclature. Nuclear spin properties and conventions for chemical shifts(IUPAC Recommendations 2001)
    journal, January 2001

    • Harris, Robin K.; Becker, Edwin D.; Cabral de Menezes, Sonia M.
    • Pure and Applied Chemistry, Vol. 73, Issue 11
    • DOI: 10.1351/pac200173111795