Amidine dications: isolation and [Fe]-hydrogenase-related hydrogenation

Michael J Corr; Kirsty F Gibson; Alan R Kennedy; John A Murphy

doi:10.1021/ja9035847

Amidine dications: isolation and [Fe]-hydrogenase-related hydrogenation

J Am Chem Soc. 2009 Jul 8;131(26):9174-5. doi: 10.1021/ja9035847.

Authors

Michael J Corr¹, Kirsty F Gibson, Alan R Kennedy, John A Murphy

Affiliation

¹ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

Abstract

This communication demonstrates the preparation, isolation, and full characterization of superelectrophilic salts based on amidine dications in organic solvent, as their triflate salts. These dications are highly activated toward regiospecific reaction with hydrogen gas under mild conditions in the presence of a metal catalyst (Pd/C), mimicking the behavior of the natural substrate, N(5),N(10)-methenyltetrahydromethanopterin, in the iron-sulfur cluster-free [Fe]-hydrogenase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Amidines / chemical synthesis
Amidines / chemistry*
Bacteria / chemistry
Bacterial Proteins / chemistry
Biomimetics
Catalysis
Cations / chemical synthesis
Cations / chemistry*
Crystallography, X-Ray
Hydrogen / chemistry*
Hydrogenase / chemistry
Hydrogenation
Iron-Sulfur Proteins / chemistry
Molecular Structure

Substances

Amidines
Bacterial Proteins
Cations
Iron-Sulfur Proteins
Hydrogen
iron hydrogenase
Hydrogenase