Amidine Dications: Isolation and [Fe]-Hydrogenase-Related Hydrogenation
Open Access
- 17 June 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (26) , 9174-9175
- https://doi.org/10.1021/ja9035847
Abstract
This commmunication 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, N5,N10-methenyltetrahydromethanopterin, in the iron−sulfur cluster-free [Fe]-hydrogenase.Keywords
This publication has 24 references indexed in Scilit:
- The crystal structure of C176A mutated [Fe]‐hydrogenase suggests an acyl‐iron ligation in the active site iron complexFEBS Letters, 2009
- The exchange activities of [Fe] hydrogenase (iron–sulfur-cluster-free hydrogenase) from methanogenic archaea in comparison with the exchange activities of [FeFe] and [NiFe] hydrogenasesJBIC Journal of Biological Inorganic Chemistry, 2007
- Readily Available Onio‐Substituted Methyleneiminium Salts: Single Precursors for a Variety of AminocarbenesAngewandte Chemie International Edition in English, 2004
- Superelectrophilic SolvationAccounts of Chemical Research, 2004
- DFT Investigation of the Tri(amino)amine N(NH2)32+ and the Tri(azido)amine N(N3)32+ Dications and Related Mixed Amino(azido)ammonium Ions (N3)xN(NH2)4-x+ (x = 0−4)1Inorganic Chemistry, 2002
- Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridineCanadian Journal of Chemistry, 2001
- Hydrogenation without a Metal Catalyst: An ab Initio Study on the Mechanism of the Metal-Free Hydrogenase from Methanobacterium thermoautotrophicumJournal of the American Chemical Society, 1998
- Geometry‐Tunable Lewis Acidity of Amidinium Cations and Its Relevance to Redox Reactions of the Thauer Metal‐Free Hydrogenase: A Theoretical StudyAngewandte Chemie International Edition in English, 1997
- On the Mechanism of Catalysis by a Metal‐Free Hydrogenase from Methanogenic Archaea: Enzymatic Transformation of H2 without a Metal and Its Analogy to the Chemistry of Alkanes in Superacidic SolutionAngewandte Chemie International Edition in English, 1995
- N5,N10‐Methylenetetrahydromethanopterin dehydrogenase from Methanobacterium thermoautotrophicum has hydrogenase activityFEBS Letters, 1990