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

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

doi:10.1007/s10870-017-0700-4

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 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.

Authors:

^[1];

^[1]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Publication Date:: Tue Oct 24 00:00:00 EDT 2017

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.

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

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                    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.  https://doi.org/10.1007/s10870-017-0700-4.  https://www.osti.gov/servlets/purl/1406230.

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@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         = {Tue Oct 24 00:00:00 EDT 2017},

  month        = {Tue Oct 24 00:00:00 EDT 2017}

}

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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

Citation Formats

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

A Simple Preparative Route to Bis(imido)uranium(VI) Complexes by the Direct Reductions of Diazenes and Azides journal, April 1998

Multi-electron reduction facilitated by a trianionic pyridine(diimine) ligand journal, January 2013

On the 75th anniversary of Prontosil journal, March 2011

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

Tuning the Oxidation State, Nuclearity, and Chemistry of Uranium Hydrides with Phenylsilane and Temperature: The Case of the Classic Uranium(III) Hydride Complex [(C 5 Me 5 ) 2 U(μ-H)] 2 journal, February 2016

Azobenzenes—synthesis and carbohydrate applications journal, December 2009

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

XCIII.—Some new azo-compounds journal, January 1895

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

2,2',4,4',6,6'-Hexaisopropylazobenzene journal, April 1981

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

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

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

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

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Uranium(III) Redox Chemistry Assisted by a Hemilabile Bis(phenolate) Cyclam Ligand: Uranium–Nitrogen Multiple Bond Formation Comprising a trans -{RN═U(VI)═NR} 2+ Complex journal, September 2015

The Photochemical Isomerization of Azobenzene 1 journal, July 1958

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

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Structural studies of the system trans-azobenzene/trans-stilbene. I. A reinvestigation of the disorder in the crystal structure of trans-azobenzene, C12H10N2 journal, August 1983

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

An NMR study of hydrogen bonding in some azo dyestuffs journal, November 1999

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

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

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

2,2',4,4',6,6'-Hexa- tert -butylazobenzene journal, November 1980

2,2',4,4',6,6'-Hexamethylazobenzene journal, April 1981

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

A Simple Preparative Route to Bis(imido)uranium(VI) Complexes by the Direct Reductions of Diazenes and Azides
journal, April 1998

Multi-electron reduction facilitated by a trianionic pyridine(diimine) ligand
journal, January 2013

On the 75th anniversary of Prontosil
journal, March 2011

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

Tuning the Oxidation State, Nuclearity, and Chemistry of Uranium Hydrides with Phenylsilane and Temperature: The Case of the Classic Uranium(III) Hydride Complex [(C ₅ Me ₅ ) ₂ U(μ-H)] ₂
journal, February 2016

Azobenzenes—synthesis and carbohydrate applications
journal, December 2009

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

XCIII.—Some new azo-compounds
journal, January 1895

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

2,2',4,4',6,6'-Hexaisopropylazobenzene
journal, April 1981

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

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

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

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

Reactivity of U ³⁺ Metallocene Allyl Complexes Leads to a Nanometer-Sized Uranium Carbonate, [(C ₅ Me ₅ ) ₂ U] ₆ (μ-κ ¹ :κ ² -CO ₃ ) ₆
journal, August 2013

Uranium(III) Redox Chemistry Assisted by a Hemilabile Bis(phenolate) Cyclam Ligand: Uranium–Nitrogen Multiple Bond Formation Comprising a trans -{RN═U(VI)═NR} ²⁺ Complex
journal, September 2015

The Photochemical Isomerization of Azobenzene ¹
journal, July 1958

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

Actinide Hydride Complexes as Multielectron Reductants: Analogous Reduction Chemistry from [(C ₅ Me ₅ ) ₂ UH] ₂ , [(C ₅ Me ₅ ) ₂ UH ₂ ] ₂ , and [(C ₅ Me ₅ ) ₂ ThH ₂ ] ₂
journal, July 2007

Structural studies of the system trans-azobenzene/trans-stilbene. I. A reinvestigation of the disorder in the crystal structure of trans-azobenzene, C12H10N2
journal, August 1983

Fast Synthesis of Hydrazine and Azo Derivatives by Oxidation of Rare-Earth-Metal−Nitrogen Bonds
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An NMR study of hydrogen bonding in some azo dyestuffs
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Elucidating the Mechanism of Uranium Mediated Diazene N═N Bond Cleavage
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journal, November 1980

2,2',4,4',6,6'-Hexamethylazobenzene
journal, April 1981