Investigation of ligand steric effect on the hydrogen gas produced via a nickel-catalyzed dehydrogenation of ammonia-borane utilizing unsymmetrical triazolylidene ligands

Meghan O. Talbot; Theresa N. Pham; Marites A. Guino-O; Ilia A. Guzei; Anastasiya I. Vinokur; Victor G. Young

doi:10.1016/j.poly.2016.02.034

Investigation of ligand steric effect on the hydrogen gas produced via a nickel-catalyzed dehydrogenation of ammonia-borane utilizing unsymmetrical triazolylidene ligands

Meghan O. Talbot, Theresa N. Pham, Marites A. Guino-O, Ilia A. Guzei, Anastasiya I. Vinokur, Victor G. Young

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Seven new unsymmetrical triazolylidene ligands 4-(4-R-phenyl)-1-R′-1,2,4-triazoly-1-lidene (where R = H, CH₃, CF₃, F; and R′ = CH₃, iPr, Bzl, methylcyclohexane) were employed in a nickel-catalyzed dehydrogenation of ammonia borane to investigate the steric effects associated with the different N(1) substitutions in the triazole ring. The bulkier substituents benzyl and methylcyclohexane afforded the highest weight percent H₂ gas produced. To quantify the steric effect, both percent buried volume (%V_bur) and solid angle G parameter (%) were employed. The G-parameter is a more useful tool when only the crystal structures of the precursor ligands are available.

Original language	English (US)
Pages (from-to)	415-421
Number of pages	7
Journal	Polyhedron
Volume	114
DOIs	https://doi.org/10.1016/j.poly.2016.02.034
State	Published - Aug 16 2016

Bibliographical note

Funding Information:
For financial support, we are indebted to the MHz Nuclear Magnetic Resonance (NMR) Spectrometer’; Dr. Daron E. Janzen, University of St. Thomas start-up funds, Partnership in Learning and Research Grant funds for M.A.G.; work-study study funds, Young Scholars and Collaborative Inquiry grants for M.T. and T.P.; the NSF–MRI grant No. 095322 ‘MRI–R2: Acquisition of a 400 St. Catherine University and the NSF–MRI grant No. 1125975 ‘MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility’; Dr. Victor Young, Jr., University of Minnesota-Twin Cities, NSF–MRI grant for the Bruker-AXS VENTURE PHOTON-100 under Award Number 1229400, and the Materials Research Facilities Network (MFRN) Program of NSF under Award Number DMR-0819885 ; Dr. Alvaro Romero, Cabrillo College, for the use vapor pressure of liquid water table.

Publisher Copyright:
© 2016 Elsevier Ltd. All rights reserved.

Keywords

Ammonia-borane
Dehydrogenation
Nickel-catalyzed
Triazolium salts
Triazolylidene ligands

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10.1016/j.poly.2016.02.034

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@article{26f997aeacb84a68842e85744479d7ba,

title = "Investigation of ligand steric effect on the hydrogen gas produced via a nickel-catalyzed dehydrogenation of ammonia-borane utilizing unsymmetrical triazolylidene ligands",

abstract = "Seven new unsymmetrical triazolylidene ligands 4-(4-R-phenyl)-1-R′-1,2,4-triazoly-1-lidene (where R = H, CH3, CF3, F; and R′ = CH3, iPr, Bzl, methylcyclohexane) were employed in a nickel-catalyzed dehydrogenation of ammonia borane to investigate the steric effects associated with the different N(1) substitutions in the triazole ring. The bulkier substituents benzyl and methylcyclohexane afforded the highest weight percent H2 gas produced. To quantify the steric effect, both percent buried volume (%Vbur) and solid angle G parameter (%) were employed. The G-parameter is a more useful tool when only the crystal structures of the precursor ligands are available.",

keywords = "Ammonia-borane, Dehydrogenation, Nickel-catalyzed, Triazolium salts, Triazolylidene ligands",

author = "Talbot, {Meghan O.} and Pham, {Theresa N.} and Guino-O, {Marites A.} and Guzei, {Ilia A.} and Vinokur, {Anastasiya I.} and Young, {Victor G.}",

note = "Funding Information: For financial support, we are indebted to the MHz Nuclear Magnetic Resonance (NMR) Spectrometer{\textquoteright}; Dr. Daron E. Janzen, University of St. Thomas start-up funds, Partnership in Learning and Research Grant funds for M.A.G.; work-study study funds, Young Scholars and Collaborative Inquiry grants for M.T. and T.P.; the NSF–MRI grant No. 095322 {\textquoteleft}MRI–R2: Acquisition of a 400 St. Catherine University and the NSF–MRI grant No. 1125975 {\textquoteleft}MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility{\textquoteright}; Dr. Victor Young, Jr., University of Minnesota-Twin Cities, NSF–MRI grant for the Bruker-AXS VENTURE PHOTON-100 under Award Number 1229400, and the Materials Research Facilities Network (MFRN) Program of NSF under Award Number DMR-0819885 ; Dr. Alvaro Romero, Cabrillo College, for the use vapor pressure of liquid water table. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. All rights reserved.",

year = "2016",

month = aug,

day = "16",

doi = "10.1016/j.poly.2016.02.034",

language = "English (US)",

volume = "114",

pages = "415--421",

journal = "Polyhedron",

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T1 - Investigation of ligand steric effect on the hydrogen gas produced via a nickel-catalyzed dehydrogenation of ammonia-borane utilizing unsymmetrical triazolylidene ligands

AU - Talbot, Meghan O.

AU - Pham, Theresa N.

AU - Guino-O, Marites A.

AU - Guzei, Ilia A.

AU - Vinokur, Anastasiya I.

AU - Young, Victor G.

N1 - Funding Information: For financial support, we are indebted to the MHz Nuclear Magnetic Resonance (NMR) Spectrometer’; Dr. Daron E. Janzen, University of St. Thomas start-up funds, Partnership in Learning and Research Grant funds for M.A.G.; work-study study funds, Young Scholars and Collaborative Inquiry grants for M.T. and T.P.; the NSF–MRI grant No. 095322 ‘MRI–R2: Acquisition of a 400 St. Catherine University and the NSF–MRI grant No. 1125975 ‘MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility’; Dr. Victor Young, Jr., University of Minnesota-Twin Cities, NSF–MRI grant for the Bruker-AXS VENTURE PHOTON-100 under Award Number 1229400, and the Materials Research Facilities Network (MFRN) Program of NSF under Award Number DMR-0819885 ; Dr. Alvaro Romero, Cabrillo College, for the use vapor pressure of liquid water table. Publisher Copyright: © 2016 Elsevier Ltd. All rights reserved.

PY - 2016/8/16

Y1 - 2016/8/16

N2 - Seven new unsymmetrical triazolylidene ligands 4-(4-R-phenyl)-1-R′-1,2,4-triazoly-1-lidene (where R = H, CH3, CF3, F; and R′ = CH3, iPr, Bzl, methylcyclohexane) were employed in a nickel-catalyzed dehydrogenation of ammonia borane to investigate the steric effects associated with the different N(1) substitutions in the triazole ring. The bulkier substituents benzyl and methylcyclohexane afforded the highest weight percent H2 gas produced. To quantify the steric effect, both percent buried volume (%Vbur) and solid angle G parameter (%) were employed. The G-parameter is a more useful tool when only the crystal structures of the precursor ligands are available.

AB - Seven new unsymmetrical triazolylidene ligands 4-(4-R-phenyl)-1-R′-1,2,4-triazoly-1-lidene (where R = H, CH3, CF3, F; and R′ = CH3, iPr, Bzl, methylcyclohexane) were employed in a nickel-catalyzed dehydrogenation of ammonia borane to investigate the steric effects associated with the different N(1) substitutions in the triazole ring. The bulkier substituents benzyl and methylcyclohexane afforded the highest weight percent H2 gas produced. To quantify the steric effect, both percent buried volume (%Vbur) and solid angle G parameter (%) were employed. The G-parameter is a more useful tool when only the crystal structures of the precursor ligands are available.

KW - Ammonia-borane

KW - Dehydrogenation

KW - Nickel-catalyzed

KW - Triazolium salts

KW - Triazolylidene ligands

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U2 - 10.1016/j.poly.2016.02.034

DO - 10.1016/j.poly.2016.02.034

M3 - Article

AN - SCOPUS:84964331165

SN - 0277-5387

VL - 114

SP - 415

EP - 421

JO - Polyhedron

JF - Polyhedron

ER -

Investigation of ligand steric effect on the hydrogen gas produced via a nickel-catalyzed dehydrogenation of ammonia-borane utilizing unsymmetrical triazolylidene ligands

Abstract

Bibliographical note

Keywords

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