Catalysis of electrochemical reduction of weak acids to produce H 2: Role of O-H..S hydrogen bonding

Jinzhu Chen; Aaron K. Vannucci; Charles A. Mebi; Noriko Okumura; Susan C. Borowski; L. Tori Lockett; Matthew Swenson; Dennis L. Lichtenberger; Dennis H. Evans; Richard S. Glass

doi:10.1080/10426507.2010.523035

Catalysis of electrochemical reduction of weak acids to produce H ₂: Role of O-H..S hydrogen bonding

Jinzhu Chen, Aaron K. Vannucci, Charles A. Mebi, Noriko Okumura, Susan C. Borowski, L. Tori Lockett, Matthew Swenson, Dennis L. Lichtenberger, Dennis H. Evans, Richard S. Glass

Chemistry and Biochemistry

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

4 Scopus citations

Abstract

The role of intramolecular OH.. S hydrogen bonding in the electrochemical reduction of protons from acetic acid using biomimetically inspired catalysts has been studied. The catalysts, hydroquinone moieties annulated to an Fe ₂S₂(CO)₆ core, were synthesized by piperidine-mediated conjugate addition of the dithiol Fe₂(SH) ₂(CO)₆ to quinones in 26-76% yields. These complexes catalyze electrochemical H₂ production from acetic acid. Evidence for weak intramolecular OH.. Shydrogen bonding in the neutral complexes is presented. Such hydrogen bonding becomes stronger as the charge increases on the sulfur in the electrochemically produced dianions due to "charge assistance," and this has chemical consequences.

Original language	English (US)
Pages (from-to)	1288-1292
Number of pages	5
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	186
Issue number	5
DOIs	https://doi.org/10.1080/10426507.2010.523035
State	Published - 2011

Keywords

Hydrogen bonding
Hydrogen production
Hydroquinone

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1080/10426507.2010.523035

Cite this

Chen, J., Vannucci, A. K., Mebi, C. A., Okumura, N., Borowski, S. C., Tori Lockett, L., Swenson, M., Lichtenberger, D. L., Evans, D. H., & Glass, R. S. (2011). Catalysis of electrochemical reduction of weak acids to produce H ₂: Role of O-H..S hydrogen bonding. Phosphorus, Sulfur and Silicon and the Related Elements, 186(5), 1288-1292. https://doi.org/10.1080/10426507.2010.523035

Chen, J, Vannucci, AK, Mebi, CA, Okumura, N, Borowski, SC, Tori Lockett, L, Swenson, M, Lichtenberger, DL, Evans, DH & Glass, RS 2011, 'Catalysis of electrochemical reduction of weak acids to produce H ₂: Role of O-H..S hydrogen bonding', Phosphorus, Sulfur and Silicon and the Related Elements, vol. 186, no. 5, pp. 1288-1292. https://doi.org/10.1080/10426507.2010.523035

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title = "Catalysis of electrochemical reduction of weak acids to produce H 2: Role of O-H..S hydrogen bonding",

abstract = "The role of intramolecular OH.. S hydrogen bonding in the electrochemical reduction of protons from acetic acid using biomimetically inspired catalysts has been studied. The catalysts, hydroquinone moieties annulated to an Fe 2S2(CO)6 core, were synthesized by piperidine-mediated conjugate addition of the dithiol Fe2(SH) 2(CO)6 to quinones in 26-76% yields. These complexes catalyze electrochemical H2 production from acetic acid. Evidence for weak intramolecular OH.. Shydrogen bonding in the neutral complexes is presented. Such hydrogen bonding becomes stronger as the charge increases on the sulfur in the electrochemically produced dianions due to {"}charge assistance,{"} and this has chemical consequences.",

keywords = "Hydrogen bonding, Hydrogen production, Hydroquinone",

author = "Jinzhu Chen and Vannucci, {Aaron K.} and Mebi, {Charles A.} and Noriko Okumura and Borowski, {Susan C.} and {Tori Lockett}, L. and Matthew Swenson and Lichtenberger, {Dennis L.} and Evans, {Dennis H.} and Glass, {Richard S.}",

note = "Funding Information: Received 17 August 2010; accepted 9 September 2010. The support of this research by the U.S. National Science Foundation is gratefully acknowledged. Address correspondence to Richard S. Glass, Department of Chemistry and Biochemistry, The University of Arizona, 1306 East University Blvd., Tucson, AZ 85721, USA. E-mail: [email protected]",

year = "2011",

doi = "10.1080/10426507.2010.523035",

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T2 - Role of O-H..S hydrogen bonding

AU - Chen, Jinzhu

AU - Vannucci, Aaron K.

AU - Mebi, Charles A.

AU - Okumura, Noriko

AU - Borowski, Susan C.

AU - Tori Lockett, L.

AU - Swenson, Matthew

AU - Lichtenberger, Dennis L.

AU - Evans, Dennis H.

AU - Glass, Richard S.

N1 - Funding Information: Received 17 August 2010; accepted 9 September 2010. The support of this research by the U.S. National Science Foundation is gratefully acknowledged. Address correspondence to Richard S. Glass, Department of Chemistry and Biochemistry, The University of Arizona, 1306 East University Blvd., Tucson, AZ 85721, USA. E-mail: [email protected]

PY - 2011

Y1 - 2011

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AB - The role of intramolecular OH.. S hydrogen bonding in the electrochemical reduction of protons from acetic acid using biomimetically inspired catalysts has been studied. The catalysts, hydroquinone moieties annulated to an Fe 2S2(CO)6 core, were synthesized by piperidine-mediated conjugate addition of the dithiol Fe2(SH) 2(CO)6 to quinones in 26-76% yields. These complexes catalyze electrochemical H2 production from acetic acid. Evidence for weak intramolecular OH.. Shydrogen bonding in the neutral complexes is presented. Such hydrogen bonding becomes stronger as the charge increases on the sulfur in the electrochemically produced dianions due to "charge assistance," and this has chemical consequences.

KW - Hydrogen bonding

KW - Hydrogen production

KW - Hydroquinone

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