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Title: Hydride oxidation from a titanium–aluminum bimetallic complex: insertion, thermal and electrochemical reactivity

Abstract

We report the synthesis and reactivity of paramagnetic heterometallic complexes containing a Ti(III)-μ-H-Al(III) moiety. Combining different stoichiometries amounts of Cp 2TiCl and KH 3AlC(TMS) 3 (Cp = cyclopentadienyl, TMS = trimethylsilyl) resulted in the formation of either bimetallic Cp 2Ti(μ-H) 2(H)AlC(TMS) 3 (2) or trimetallic (Cp 2Ti) 2(μ-H) 3(H)AlC(TMS) 3 (3) via salt metathesis pathways. While these complexes were indefinitely stable at room temperature, the bridging hydrides were readily activated upon exposure to heteroallenes, heating, or electrochemical oxidation. In each case, formal hydride oxidation occurred, but the isolated product maintained the +3 oxidation state at both metal centers. The nature of this reactivity was explored using deuterium labelling experiments and Density Functional Theory (DFT) calculations. It was found that while C–H activation from the Ti(III) bimetallic may occur through a σ-bond metathesis pathway, chemical oxidation to Ti(IV) promotes bimolecular reductive elimination of dihydrogen to form a Ti(III) product.

Authors:
 [1];  [2]; ORCiD logo [2]; ORCiD logo [2]; ORCiD logo [2]
  1. Univ. of California, Berkeley, CA (United States)
  2. Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1399463
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 8; Journal Issue: 7; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Brown, Alexandra C., Altman, Alison B., Lohrey, Trevor D., Hohloch, Stephan, and Arnold, John. Hydride oxidation from a titanium–aluminum bimetallic complex: insertion, thermal and electrochemical reactivity. United States: N. p., 2017. Web. doi:10.1039/c7sc01835e.
Brown, Alexandra C., Altman, Alison B., Lohrey, Trevor D., Hohloch, Stephan, & Arnold, John. Hydride oxidation from a titanium–aluminum bimetallic complex: insertion, thermal and electrochemical reactivity. United States. doi:10.1039/c7sc01835e.
Brown, Alexandra C., Altman, Alison B., Lohrey, Trevor D., Hohloch, Stephan, and Arnold, John. Wed . "Hydride oxidation from a titanium–aluminum bimetallic complex: insertion, thermal and electrochemical reactivity". United States. doi:10.1039/c7sc01835e. https://www.osti.gov/servlets/purl/1399463.
@article{osti_1399463,
title = {Hydride oxidation from a titanium–aluminum bimetallic complex: insertion, thermal and electrochemical reactivity},
author = {Brown, Alexandra C. and Altman, Alison B. and Lohrey, Trevor D. and Hohloch, Stephan and Arnold, John},
abstractNote = {We report the synthesis and reactivity of paramagnetic heterometallic complexes containing a Ti(III)-μ-H-Al(III) moiety. Combining different stoichiometries amounts of Cp2TiCl and KH3AlC(TMS)3 (Cp = cyclopentadienyl, TMS = trimethylsilyl) resulted in the formation of either bimetallic Cp2Ti(μ-H)2(H)AlC(TMS)3 (2) or trimetallic (Cp2Ti)2(μ-H)3(H)AlC(TMS)3 (3) via salt metathesis pathways. While these complexes were indefinitely stable at room temperature, the bridging hydrides were readily activated upon exposure to heteroallenes, heating, or electrochemical oxidation. In each case, formal hydride oxidation occurred, but the isolated product maintained the +3 oxidation state at both metal centers. The nature of this reactivity was explored using deuterium labelling experiments and Density Functional Theory (DFT) calculations. It was found that while C–H activation from the Ti(III) bimetallic may occur through a σ-bond metathesis pathway, chemical oxidation to Ti(IV) promotes bimolecular reductive elimination of dihydrogen to form a Ti(III) product.},
doi = {10.1039/c7sc01835e},
journal = {Chemical Science},
number = 7,
volume = 8,
place = {United States},
year = {2017},
month = {5}
}

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Cited by: 3 works
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Figures / Tables:

Figure 1 Figure 1: Previously synthesized transition metal aluminum hydride heterometallics I,39 II,31 III,29 IV22 and V41 showing the variousmotifs that have been isolated.

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    Works referencing / citing this record:

    Improved Hydrogen Storage Properties of Ti-Doped Sodium Alanate Using Titanium Nanoparticles as Doping Agents
    journal, June 2003

    • Bogdanović, B.; Felderhoff, M.; Kaskel, S.
    • Advanced Materials, Vol. 15, Issue 12
    • DOI: 10.1002/adma.200304711

    Zirconocene Dichloride Catalyzed Hydrodefluorination of C sp 2F bonds
    journal, November 2012

    • Yow, Shuhui; Gates, Sarah J.; White, Andrew J. P.
    • Angewandte Chemie International Edition, Vol. 51, Issue 50
    • DOI: 10.1002/anie.201207036

    A Frustrated and Confused Lewis Pair
    journal, October 2016

    • McQuilken, Alison C.; Dao, Quang Minh; Cardenas, Allan Jay P.
    • Angewandte Chemie International Edition, Vol. 55, Issue 46
    • DOI: 10.1002/anie.201608968

    Syntheses and Structures of Ruthenium Complexes Containing a Ru-H-Tl Three-Center-Two-Electron Bond
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    • Bai, Wei; Zhang, Jing-Xuan; Fan, Ting
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    Ti-doped NaAlH4 as a hydrogen-storage material – preparation by Ti-catalyzed hydrogenation of aluminum powder in conjunction with sodium hydride
    journal, February 2001

    • Bogdanović, B.; Schwickardi, M.
    • Applied Physics A Materials Science & Processing, Vol. 72, Issue 2
    • DOI: 10.1007/s003390100774

    The U.S. Department of Energy's National Hydrogen Storage Project: Progress towards meeting hydrogen-powered vehicle requirements
    journal, February 2007


    Metal hydride materials for solid hydrogen storage: A review☆
    journal, June 2007


    Rehydrogenation and cycling studies of dehydrogenated NaAlH4
    journal, June 2004


    Method for preparing Ti-doped NaAlH4 using Ti powder: observation of an unusual reversible dehydrogenation behavior
    journal, October 2004


    Aluminum hydride as a hydrogen and energy storage material: Past, present and future
    journal, September 2011


    Complex Hydrides for Hydrogen Storage
    journal, October 2007

    • Orimo, Shin-ichi; Nakamori, Yuko; Eliseo, Jennifer R.
    • Chemical Reviews, Vol. 107, Issue 10
    • DOI: 10.1021/cr0501846

    Utilizing the Evans method with a superconducting NMR spectrometer in the undergraduate laboratory
    journal, January 1992

    • Schubert, Ernest M.
    • Journal of Chemical Education, Vol. 69, Issue 1
    • DOI: 10.1021/ed069p62.1

    Paramagnetic Susceptibility by NMR: The "Solvent Correction" Removed for Large Paramagnetic Molecules
    journal, July 1997

    • Piguet, Claude
    • Journal of Chemical Education, Vol. 74, Issue 7
    • DOI: 10.1021/ed074p815

    Diamagnetic Corrections and Pascal's Constants
    journal, April 2008

    • Bain, Gordon A.; Berry, John F.
    • Journal of Chemical Education, Vol. 85, Issue 4
    • DOI: 10.1021/ed085p532

    An unprecedented, bridged dihydrogen complex of a cofacial metallodiporphyrin and its relevance to the bimolecular reductive elimination of hydrogen
    journal, October 1990

    • Collman, James P.; Hutchison, James E.; Wagenknecht, Paul S.
    • Journal of the American Chemical Society, Vol. 112, Issue 22
    • DOI: 10.1021/ja00178a077

    Aluminotitanium hydrides [(C5H5)Ti]2(H)(H2AlEt2)C10H8) and [(C5H4)TiHAlEt2]2(C10H8)
    journal, November 1973

    • Guggenberger, Lloyd J.; Tebbe, Fred N.
    • Journal of the American Chemical Society, Vol. 95, Issue 23
    • DOI: 10.1021/ja00804a055

    Di-.mu.-hydrido-bis(dicyclopentadienyltitanium(III)), a transition metal complex with a diborane-like double hydrogen bridge
    journal, December 1969

    • Bercaw, John E.; Brintzinger, Hans H.
    • Journal of the American Chemical Society, Vol. 91, Issue 26
    • DOI: 10.1021/ja01054a018

    Oxidative Addition of σ Bonds to an Al(I) Center
    journal, June 2014

    • Chu, Terry; Korobkov, Ilia; Nikonov, Georgii I.
    • Journal of the American Chemical Society, Vol. 136, Issue 25
    • DOI: 10.1021/ja5038337

    Theory and X-ray Absorption Spectroscopy for Aluminum Coordination Complexes – Al K-Edge Studies of Charge and Bonding in (BDI)Al, (BDI)AlR 2 , and (BDI)AlX 2 Complexes
    journal, August 2015

    • Altman, Alison B.; Pemmaraju, C. D.; Camp, Clément
    • Journal of the American Chemical Society, Vol. 137, Issue 32
    • DOI: 10.1021/jacs.5b05854

    Kinetic Study and Determination of the Enthalpies of Activation of the Dehydrogenation of Titanium- and Zirconium-Doped NaAlH 4 and Na 3 AlH 6
    journal, October 2003

    • Kiyobayashi, Tetsu; Srinivasan, Sesha S.; Sun, Dalin
    • The Journal of Physical Chemistry A, Vol. 107, Issue 39
    • DOI: 10.1021/jp034543h

    The Role of Ti in Alanates and Borohydrides: Catalysis and Metathesis
    journal, December 2013

    • Callini, Elsa; Borgschulte, Andreas; Hugelshofer, Cedric L.
    • The Journal of Physical Chemistry C, Vol. 118, Issue 1
    • DOI: 10.1021/jp407999r

    Preparation of New Lithium Organotrihydroaluminates: Crystal Structure of {(C4H8O)2Li(.mu.-H)2AlH[C(SiMe2Ph)3]}2
    journal, November 1994

    • Eaborn, Colin; Gorrell, Ian B.; Hitchcock, Peter B.
    • Organometallics, Vol. 13, Issue 11
    • DOI: 10.1021/om00023a007

    Hydroalumination of Alkenes and Alkynes by Primary Aluminum Hydrides under Mild Conditions
    journal, October 2014

    • Fettinger, James C.; Gray, Paul A.; Melton, Christopher E.
    • Organometallics, Vol. 33, Issue 21
    • DOI: 10.1021/om500911f

    Hydride-Bridged Heterobimetallic Complexes of Zirconium and Aluminum
    journal, July 1997

    • Khan, Karl; Raston, Colin L.; McGrady, John E.
    • Organometallics, Vol. 16, Issue 15
    • DOI: 10.1021/om970141i

    Synthesis, Structure, and Reducing Ability of a Stable Organotrihydroaluminate Bearing a Novel Bowl-Type Substituent
    journal, April 1999

    • Goto, Kei; Kobayashi, Junji; Okazaki, Renji
    • Organometallics, Vol. 18, Issue 8
    • DOI: 10.1021/om9805032

    Turning aluminium into a noble-metal-like catalyst for low-temperature activation of molecular hydrogen
    journal, September 2011

    • Chopra, Irinder S.; Chaudhuri, Santanu; Veyan, Jean François
    • Nature Materials, Vol. 10, Issue 11
    • DOI: 10.1038/nmat3123

    Covalent radii revisited
    journal, January 2008

    • Cordero, Beatriz; Gómez, Verónica; Platero-Prats, Ana E.
    • Dalton Transactions, Issue 21
    • DOI: 10.1039/b801115j

    Structure of the aluminotitanium hydride [(C5H5)(C5H4)TiHAl(C2H5)2]2
    journal, January 1973

    • Tebbe, Fred N.; Guggenberger, Lloyd J.
    • Journal of the Chemical Society, Chemical Communications, Issue 6
    • DOI: 10.1039/c39730000227

    Reductive elimination: a pathway to low-valent aluminium species
    journal, January 2013

    • Ganesamoorthy, Chelladurai; Loerke, Sinah; Gemel, Christian
    • Chemical Communications, Vol. 49, Issue 28
    • DOI: 10.1039/c3cc38584a

    Group 4 metallocene catalysed full dehydrogenation of hydrazine borane
    journal, January 2013

    • Thomas, Johannes; Klahn, Marcus; Spannenberg, Anke
    • Dalton Transactions, Vol. 42, Issue 41
    • DOI: 10.1039/c3dt51370j

    Tertiary phosphine aluminohydride complexes of chromium-, molybdenum-, and tungsten-(II)
    journal, January 1986

    • Barron, Andrew R.; Salt, Julian E.; Wilkinson, Geoffrey
    • Journal of the Chemical Society, Dalton Transactions, Issue 7
    • DOI: 10.1039/dt9860001329

    Small Ti clusters for catalysis of hydrogen exchange in NaAlH 4
    journal, May 2003