Anion control of tautomeric equilibria: Fe–H vs. N–H influenced by NH⋯F hydrogen bonding

Chambers, Geoffrey M.; Johnson, Samantha I.; Raugei, Simone; Bullock, R. Morris

doi:10.1039/C8SC04239J

Title: Anion control of tautomeric equilibria: Fe–H vs. N–H influenced by NH⋯F hydrogen bonding

Journal Article · 30 January 2019 · Chemical Science

DOI: https://doi.org/10.1039/C8SC04239J · OSTI ID:1483140

Chambers, Geoffrey M. ^[1];

^[1];

^[1]

Center for Molecular Electrocatalysis, Pacific Northwest National Laboratory, Richland, USA

Addition of excess BF ₄ ⁻ to the iron hydride [Fe(P ^Et N ^Me P ^Et )(CO) ₃ H] ⁺ [B(C ₆ F ₅ ) ₄ ] ⁻ leads to the NH tautomer, due to NH⋯F hydrogen bonding.

View Journal Article

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Molecular Electrocatalysis (CME); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1483140

Report Number(s):: PNNL-SA--135803

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 5 Vol. 10; ISSN 2041-6520; ISSN CSHCBM

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (71)

A Well-Defined Iron Catalyst for the Reduction of Bicarbonates and Carbon Dioxide to Formates, Alkyl Formates, and Formamides Federsel, Christopher; Boddien, Albert; Jackstell, Ralf Angewandte Chemie International Edition, Vol. 49, Issue 50 https://doi.org/10.1002/anie.201004263	journal	November 2010
Counteranion-Directed Catalysis in the Tsuji-Trost Reaction: Stereocontrolled Access to 2,5-Disubstituted 3-Hydroxy-Tetrahydrofurans Arthuis, Martin; Beaud, Rodolphe; Gandon, Vincent Angewandte Chemie International Edition, Vol. 51, Issue 42 https://doi.org/10.1002/anie.201205479	journal	September 2012
Heterolytic Cleavage of Hydrogen by an Iron Hydrogenase Model: An Fe-H⋅⋅⋅H-N Dihydrogen Bond Characterized by Neutron Diffraction Liu, Tianbiao; Wang, Xiaoping; Hoffmann, Christina Angewandte Chemie International Edition, Vol. 53, Issue 21 https://doi.org/10.1002/anie.201402090	journal	April 2014
Controlling Proton Delivery through Catalyst Structural Dynamics Cardenas, Allan Jay P.; Ginovska, Bojana; Kumar, Neeraj Angewandte Chemie International Edition, Vol. 55, Issue 43 https://doi.org/10.1002/anie.201607460	journal	September 2016
Experimental and Computational Studies of Hydrogen Bonding and Proton Transfer to [Cp*Fe(dppe)H] Belkova, Natalia V.; Collange, Edmond; Dub, Pavel Chemistry - A European Journal, Vol. 11, Issue 3 https://doi.org/10.1002/chem.200400700	journal	December 2004
Solvent-Dependent Dihydrogen/Dihydride Stability for [Mo(CO)(Cp*)H ₂ (PMe ₃ ) ₂ ] ⁺ [BF ₄ ] ^âˆ’ Determined by Multiple Solventâ‹…â‹…â‹…Anionâ‹…â‹…â‹…Cation Non-Covalent Interactions Dub, PavelâA.; Belkova, NataliaâV.; Filippov, OlegâA. Chemistry - A European Journal, Vol. 16, Issue 1 https://doi.org/10.1002/chem.200901613	journal	January 2010
Group 13 Complexes of 5-Methyl-1,3,5-dithiazinane Gálvez-Ruiz, Juan Carlos; Guadarrama-Pérez, Carlos; Nöth, Heinrich European Journal of Inorganic Chemistry, Vol. 2004, Issue 3 https://doi.org/10.1002/ejic.200300385	journal	February 2004
Dihydrogen Bonding, Proton Transfer and Beyond: What We Can Learn from Kinetics and Thermodynamics Belkova, Natalia V.; Epstein, Lina M.; Shubina, Elena S. European Journal of Inorganic Chemistry, Vol. 2010, Issue 23 https://doi.org/10.1002/ejic.201000546	journal	July 2010
Theoretical studies of O2?:(H2O)n clusters Curtiss, Larry A.; Melendres, Carlos A.; Reed, Alan E. Journal of Computational Chemistry, Vol. 7, Issue 3 https://doi.org/10.1002/jcc.540070307	journal	June 1986
Interaction between [(η5-C5Me5)2 OsH]+PF6− and nitrogen or oxygen bases. Hydrogen bonds of the type [OsH]+ ⋯ B Epstein, L. M.; Shubina, E. S.; Krylov, A. N. Journal of Organometallic Chemistry, Vol. 447, Issue 2 https://doi.org/10.1016/0022-328X(93)80250-F	journal	April 1993
New types of hydrogen bonding in organometallic chemistry Epstein, Lina M.; Shubina, Elena S. Coordination Chemistry Reviews, Vol. 231, Issue 1-2 https://doi.org/10.1016/S0010-8545(02)00118-2	journal	September 2002
Recent advances in hydrogen bonding studies involving metal hydrides Crabtree, Robert H. Journal of Organometallic Chemistry, Vol. 557, Issue 1 https://doi.org/10.1016/S0022-328X(97)00738-9	journal	April 1998
Dihydrogen, dihydride and in between: NMR and structural properties of iron group complexes Morris, Robert H. Coordination Chemistry Reviews, Vol. 252, Issue 21-22 https://doi.org/10.1016/j.ccr.2008.01.010	journal	November 2008
Molecular Electrocatalysts for Oxidation of Hydrogen Using Earth-Abundant Metals: Shoving Protons Around with Proton Relays Bullock, R. Morris; Helm, Monte L. Accounts of Chemical Research, Vol. 48, Issue 7 https://doi.org/10.1021/acs.accounts.5b00069	journal	June 2015
Brønsted–Lowry Acid Strength of Metal Hydride and Dihydrogen Complexes Morris, Robert H. Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.5b00695	journal	March 2016
Hydrogen and Dihydrogen Bonds in the Reactions of Metal Hydrides Belkova, Natalia V.; Epstein, Lina M.; Filippov, Oleg A. Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00091	journal	June 2016
Experimental and Computational Mechanistic Studies Guiding the Rational Design of Molecular Electrocatalysts for Production and Oxidation of Hydrogen Raugei, Simone; Helm, Monte L.; Hammes-Schiffer, Sharon Inorganic Chemistry, Vol. 55, Issue 2 https://doi.org/10.1021/acs.inorgchem.5b02262	journal	November 2015
Redox Induced Configurational Isomerization of Bisphosphine–Tricarbonyliron(I) Complexes and the Difference a Ferrocene Makes Ringenberg, Mark R.; Wittkamp, Florian; Apfel, Ulf-Peter Inorganic Chemistry, Vol. 56, Issue 13 https://doi.org/10.1021/acs.inorgchem.7b00957	journal	June 2017
Explicitly Unraveling the Roles of Counterions, Solvent Molecules, and Electron Correlation in Solution Phase Reaction Pathways Groenenboom, Mitchell C.; Keith, John A. The Journal of Physical Chemistry B, Vol. 120, Issue 41 https://doi.org/10.1021/acs.jpcb.6b07606	journal	October 2016
Sterically crowded stable simple enols Rappoport, Zvi; Biali, Silvio E. Accounts of Chemical Research, Vol. 21, Issue 12 https://doi.org/10.1021/ar00156a002	journal	December 1988
Flash photolytic generation and study of reactive species: from enols to ynols Kresge, A. Jerry Accounts of Chemical Research, Vol. 23, Issue 2 https://doi.org/10.1021/ar00170a005	journal	February 1990
Diverse World of Unconventional Hydrogen Bonds Belkova, Natalia V.; Shubina, Elena S.; Epstein, Lina M. Accounts of Chemical Research, Vol. 38, Issue 8 https://doi.org/10.1021/ar040006j	journal	August 2005
Dihydrogen Bonding: Structures, Energetics, and Dynamics Custelcean, Radu; Jackson, James E. Chemical Reviews, Vol. 101, Issue 7 https://doi.org/10.1021/cr000021b	journal	July 2001
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Reed, Alan E.; Curtiss, Larry A.; Weinhold, Frank Chemical Reviews, Vol. 88, Issue 6 https://doi.org/10.1021/cr00088a005	journal	September 1988
Ion Pairing in Transition-Metal Organometallic Chemistry Macchioni, Alceo Chemical Reviews, Vol. 105, Issue 6 https://doi.org/10.1021/cr0300439	journal	June 2005
Fundamentals of H ₂ Binding and Reactivity on Transition Metals Underlying Hydrogenase Function and H ₂ Production and Storage Kubas, Gregory J. Chemical Reviews, Vol. 107, Issue 10 https://doi.org/10.1021/cr050197j	journal	October 2007
Mechanistic Insights on Cooperative Catalysis through Computational Quantum Chemical Methods Jindal, Garima; Kisan, Hemanta K.; Sunoj, Raghavan B. ACS Catalysis, Vol. 5, Issue 2 https://doi.org/10.1021/cs501688y	journal	December 2014
Di-Iron Aza Diphosphido Complexes: Mimics for the Active Site of Fe-Only Hydrogenase, and Effects of Changing the Coordinating Atoms of the Bridging Ligand in [Fe₂{μ-(ECH₂)₂NR}(CO)₆] Das, Pankaj; Capon, Jean-François; Gloaguen, Frédéric Inorganic Chemistry, Vol. 43, Issue 26 https://doi.org/10.1021/ic048772+	journal	November 2004
Dihydrogen to Dihydride Isomerization Mechanism in [(C ₅ Me ₅ )FeH ₂ (Ph ₂ PCH ₂ CH ₂ PPh ₂ )] ⁺ through the Experimental and Theoretical Analysis of Kinetic Isotope Effects Baya, Miguel; Maresca, Olivier; Poli, Rinaldo Inorganic Chemistry, Vol. 45, Issue 25 https://doi.org/10.1021/ic061428n	journal	December 2006
Development of Molecular Electrocatalysts for Energy Storage DuBois, Daniel L. Inorganic Chemistry, Vol. 53, Issue 8 https://doi.org/10.1021/ic4026969	journal	February 2014
Investigation of the [Cp*Mo(PMe ₃ ) ₃ H] ^{n +} ( n = 0, 1) Redox Pair: Dynamic Processes on Very Different Time Scales Baya, Miguel; Dub, Pavel A.; Houghton, Jennifer Inorganic Chemistry, Vol. 48, Issue 1 https://doi.org/10.1021/ic801676n	journal	January 2009
.eta.2-Dihydrogen on the brink of homolytic cleavage: trans-[Os(H.cntdot..cntdot..cntdot.H)H(PEt2CH2CH2PEt2)2]+ has spectroscopic and chemical properties between those of the isoelectronic complexes trans-[OsH(PPh2CH2CH2PPh2)2(.eta.2-H2)]+ and ReH3(PPh2CH2CH2PPh2)2 Earl, Kelly A.; Jia, Guochen; Maltby, Patricia A. Journal of the American Chemical Society, Vol. 113, Issue 8 https://doi.org/10.1021/ja00008a035	journal	April 1991
Switching On and Off a New Intramolecular Hydrogen-Hydrogen Interaction and the Heterolytic Splitting of Dihydrogen. Crystal and Molecular Structure of [Ir{H(.eta.1-SC5H4NH)}2(PCy3)2]BF4.cntdot.2.7CH2Cl2 Lough, Alan J.; Park, Sunghan; Ramachandran, Ravindranath Journal of the American Chemical Society, Vol. 116, Issue 18 https://doi.org/10.1021/ja00097a049	journal	September 1994
An Unusual Type of H.cntdot..cntdot..cntdot.H Interaction: Ir-H.cntdot..cntdot..cntdot.H-O and Ir-H.cntdot..cntdot..cntdot.H-N Hydrogen Bonding and Its Involvement in .sigma.-Bond Metathesis Lee, Jesse C.; Peris, Eduardo; Rheingold, Arnold L. Journal of the American Chemical Society, Vol. 116, Issue 24 https://doi.org/10.1021/ja00103a017	journal	November 1994
Synthesis of the First Examples of Transition Metal .eta.2-SiH4 Complexes, cis-Mo(.eta.2-SiH4)(CO)(R2PC2H4PR2)2, and Evidence for an Unprecedented Tautomeric Equilibrium between an .eta.2-SiH4 Complex and a Hydridosilyl Species: A Model for Methane Coordination and Activation Luo, Xiao-Liang; Kubas, Gregory J.; Burns, Carol J. Journal of the American Chemical Society, Vol. 117, Issue 3 https://doi.org/10.1021/ja00108a045	journal	January 1995
Dihydrogen complexes of ruthenium. 2. Kinetic and thermodynamic considerations affecting product distribution Chinn, Mitchell S.; Heinekey, D. Michael Journal of the American Chemical Society, Vol. 112, Issue 13 https://doi.org/10.1021/ja00169a026	journal	June 1990
Solution equilibrium between classical and nonclassical polyhydride tautomers [ReH4(CO)L3]+ and [ReH2(.eta.2-H2)(CO)L3]+ (L = PMe2Ph). Equilibrium isotope effects and an intermediate trihydrogen complex in intramolecular site exchange of dihydrogen and hydride ligands Luo, Xiao Liang; Crabtree, Robert H. Journal of the American Chemical Society, Vol. 112, Issue 19 https://doi.org/10.1021/ja00175a027	journal	September 1990
Kinetic and thermodynamic acidity of hydrido transition-metal complexes. 4. Kinetic acidities toward aniline and their use in identifying proton-transfer mechanisms Edidin, Robin T.; Sullivan, Jeffrey M.; Norton, Jack R. Journal of the American Chemical Society, Vol. 109, Issue 13 https://doi.org/10.1021/ja00247a019	journal	June 1987
Synthesis and properties of a series of ruthenium dihydrogen complexes Chinn, Mitchell S.; Heinekey, D. Michael Journal of the American Chemical Society, Vol. 109, Issue 19 https://doi.org/10.1021/ja00253a057	journal	September 1987
Molecular hydrogen complexes of the transition metals. 3. Evidence for a new complex, Mo(CO)(dppe)2(H2), and for solution equilibrium between dihydrogen and dihydride forms, M-.eta.2-H2 .dblarw. H-M-H, in M(CO)3(PR3)2(H2) Kubas, Gregory J.; Ryan, R. R.; Wrobleski, Debra A. Journal of the American Chemical Society, Vol. 108, Issue 6 https://doi.org/10.1021/ja00266a058	journal	March 1986
Kinetic and thermodynamic acidity of hydrido transition-metal complexes. 3. Thermodynamic acidity of common mononuclear carbonyl hydrides Moore, Eric J.; Sullivan, Jeffrey M.; Norton, Jack R. Journal of the American Chemical Society, Vol. 108, Issue 9 https://doi.org/10.1021/ja00269a022	journal	April 1986
Tricarbonylbis(phosphine)iron(I) cation radicals. A spectroscopic and theoretical study Therien, Michael J.; Trogler, William C. Journal of the American Chemical Society, Vol. 108, Issue 13 https://doi.org/10.1021/ja00273a025	journal	June 1986
Molecular hydrogen complexes of the transition metals. 4. Preparation and characterization of M(CO)3(PR3)2(.eta.2-H2) (M = molybdenum, tungsten) and evidence for equilibrium dissociation of the H-H bond to give MH2(CO)3(PR3)2 Kubas, Gregory J.; Unkefer, Clifford J.; Swanson, Basil I. Journal of the American Chemical Society, Vol. 108, Issue 22 https://doi.org/10.1021/ja00282a026	journal	October 1986
The pKa and keto-enol equilibrium constant of acetone in aqueous solution Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S. Journal of the American Chemical Society, Vol. 106, Issue 2 https://doi.org/10.1021/ja00314a055	journal	January 1984
H−H Distances in Elongated Transition Metal Dihydrogen Complexes: Effects of Temperature and Isotopic Substitution Law, James K.; Mellows, Heather; Heinekey, D. Michael Journal of the American Chemical Society, Vol. 123, Issue 9 https://doi.org/10.1021/ja005536z	journal	March 2001
Synthesis and Spectroscopic Properties of Elongated Ruthenium Dihydrogen Complexes: Temperature and Isotope Dependence of H−H Distances Law, James K.; Mellows, Heather; Heinekey, D. Michael Journal of the American Chemical Society, Vol. 124, Issue 6 https://doi.org/10.1021/ja0118284	journal	February 2002
Kinetics and Mechanism of the Proton Transfer to Cp*Fe(dppe)H: Absence of a Direct Protonation at the Metal Site Belkova, Natalia V.; Revin, Pavel O.; Epstein, Lina M. Journal of the American Chemical Society, Vol. 125, Issue 36 https://doi.org/10.1021/ja0358450	journal	September 2003
Intermolecular Hydrogen Bonding between Neutral Transition Metal Hydrides (η ⁵ -C ₅ H ₅ )M(CO) ₃ H (M = Mo, W) and Bases Belkova, Natalia V.; Gutsul, Evgenii I.; Filippov, Oleg A. Journal of the American Chemical Society, Vol. 128, Issue 11 https://doi.org/10.1021/ja057867n	journal	March 2006
Crucial Role of Anions on the Deprotonation of the Cationic Dihydrogen Complex trans -[FeH(η ² -H ₂ )(dppe) ₂ ] ⁺ Basallote, Manuel G.; Besora, Maria; Castillo, C. Esther Journal of the American Chemical Society, Vol. 129, Issue 20 https://doi.org/10.1021/ja070939l	journal	May 2007
Role of the Azadithiolate Cofactor in Models for [FeFe]-Hydrogenase: Novel Structures and Catalytic Implications Olsen, Matthew T.; Rauchfuss, Thomas B.; Wilson, Scott R. Journal of the American Chemical Society, Vol. 132, Issue 50 https://doi.org/10.1021/ja103998v	journal	December 2010
Mild Redox Complementation Enables H ₂ Activation by [FeFe]-Hydrogenase Models Camara, James M.; Rauchfuss, Thomas B. Journal of the American Chemical Society, Vol. 133, Issue 21 https://doi.org/10.1021/ja201731q	journal	June 2011
Moving Protons with Pendant Amines: Proton Mobility in a Nickel Catalyst for Oxidation of Hydrogen O’Hagan, Molly; Shaw, Wendy J.; Raugei, Simone Journal of the American Chemical Society, Vol. 133, Issue 36, p. 14301-14312 https://doi.org/10.1021/ja201838x	journal	September 2011
A Nonclassical Dihydrogen Adduct of S = ¹ / ₂ Fe(I) Lee, Yunho; Kinney, R. Adam; Hoffman, Brian M. Journal of the American Chemical Society, Vol. 133, Issue 41 https://doi.org/10.1021/ja207003m	journal	October 2011
Proton Delivery and Removal in [Ni(P ^R ₂ N ^{R ^′} ₂ ) ₂ ] ²⁺ Hydrogen Production and Oxidation Catalysts O’Hagan, Molly; Ho, Ming-Hsun; Yang, Jenny Y. Journal of the American Chemical Society, Vol. 134, Issue 47 https://doi.org/10.1021/ja307413x	journal	November 2012
Synthetic Models for the Active Site of the [FeFe]-Hydrogenase: Catalytic Proton Reduction and the Structure of the Doubly Protonated Intermediate Carroll, Maria E.; Barton, Bryan E.; Rauchfuss, Thomas B. Journal of the American Chemical Society, Vol. 134, Issue 45 https://doi.org/10.1021/ja309216v	journal	November 2012
Hydrogen Activation by Biomimetic [NiFe]-Hydrogenase Model Containing Protected Cyanide Cofactors Manor, Brian C.; Rauchfuss, Thomas B. Journal of the American Chemical Society, Vol. 135, Issue 32 https://doi.org/10.1021/ja404580r	journal	July 2013
Spectroscopic Evidence for Intermolecular M−H···H−OR Hydrogen Bonding: Interaction of WH(CO) ₂ (NO)L ₂ Hydrides with Acidic Alcohols Shubina, Elena S.; Belkova, Natalia V.; Krylov, Aleksandr N. Journal of the American Chemical Society, Vol. 118, Issue 5 https://doi.org/10.1021/ja953094z	journal	January 1996
Electrostatic Control of Regioselectivity in Au(I)-Catalyzed Hydroarylation Lau, Vivian M.; Pfalzgraff, William C.; Markland, Thomas E. Journal of the American Chemical Society, Vol. 139, Issue 11 https://doi.org/10.1021/jacs.6b11971	journal	March 2017
Iron Complexes Bearing Diphosphine Ligands with Positioned Pendant Amines as Electrocatalysts for the Oxidation of H ₂ Liu, Tianbiao; Liao, Qian; O’Hagan, Molly Organometallics, Vol. 34, Issue 12 https://doi.org/10.1021/om501289f	journal	May 2015
Synthesis, Structure, and Properties of the Stable and Highly Acidic Dihydrogen Complex trans -[Os(η ² -H ₂ )(CH ₃ CN)(dppe) ₂ ](BF ₄ ) ₂ . Perspectives on the Influence of the trans Ligand on the Chemistry of the Dihydrogen Ligand Schlaf, Marcel; Lough, Alan J.; Maltby, Patricia A. Organometallics, Vol. 15, Issue 9 https://doi.org/10.1021/om960113k	journal	January 1996
Intramolecular N−H···H−Ru Proton−Hydride Interaction in Ruthenium Complexes with (2-(Dimethylamino)ethyl)cyclopentadienyl and (3-(Dimethylamino)propyl)cyclopentadienyl Ligands. Hydrogenation of CO ₂ to Formic Acid via the N−H···H−Ru Hydrogen-Bonded Complexes Chu, Hei Shing; Lau, Chak Po; Wong, Kwok Yin Organometallics, Vol. 17, Issue 13 https://doi.org/10.1021/om980071v	journal	June 1998
An iron complex with pendent amines as a molecular electrocatalyst for oxidation of hydrogen Liu, Tianbiao; DuBois, Daniel L.; Bullock, R. Morris Nature Chemistry, Vol. 5, Issue 3 https://doi.org/10.1038/nchem.1571	journal	February 2013
Elongated dihydrogen complexes: what remains of the H–H Bond? Heinekey, D. Michael; Lledós, Agustí; Lluch, José M. Chem. Soc. Rev., Vol. 33, Issue 3 https://doi.org/10.1039/B304879A	journal	January 2004
Intramolecular N–H ⋯ X–Ir (X = H, F) hydrogen bonding in metal complexes Peris, Eduardo; Lee, Jesse C.; Crabtree, Robert H. J. Chem. Soc., Chem. Commun., Issue 22 https://doi.org/10.1039/C39940002573	journal	January 1994
Infrared detection of M–H ⋯ OPPh ₃ hydrogen bonds Peris, Eduardo; Crabtree, Robert H. J. Chem. Soc., Chem. Commun., Issue 21 https://doi.org/10.1039/C39950002179	journal	January 1995
Gold( iii ) tetraarylporphyrin amino acid derivatives: ligand or metal centred redox chemistry? Preiß, Sebastian; Melomedov, Jascha; Wünsche von Leupoldt, Anica Chemical Science, Vol. 7, Issue 1 https://doi.org/10.1039/C5SC03429A	journal	January 2016
The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts Dub, Pavel A.; Gordon, John C. Dalton Transactions, Vol. 45, Issue 16 https://doi.org/10.1039/C6DT00476H	journal	January 2016
Harnessing non-covalent interactions to exert control over regioselectivity and site-selectivity in catalytic reactions Davis, Holly J.; Phipps, Robert J. Chemical Science, Vol. 8, Issue 2 https://doi.org/10.1039/C6SC04157D	journal	January 2017
Synthesis of the acidic dihydrogen complexes trans-[M(H2)(CN)L2]+ and trans-[M(H2)(CNH)L2]2+ where M = Fe, Ru, Os and L = dppm, dppe, dppp, depe, and dihydrogen substitution by the trifluoromethanesulfonate anion to give trans-[Ru(OTf )(CN)L2] or trans-[Ru(OTf )(CNH)L2]OTf † Fong, Tina P.; Forde, Cameron E.; Lough, Alan J. Journal of the Chemical Society, Dalton Transactions, Issue 24 https://doi.org/10.1039/a906717e	journal	January 1999
Metals and hydrogen bonds Brammer, Lee Dalton Transactions, Issue 16 https://doi.org/10.1039/b303006g	journal	January 2003
Trimethylammonium tetrafluoroborate at 100 K Gotoh, Kazuma; Ishikawa, Rie; Ishida, Hiroyuki Acta Crystallographica Section E Structure Reports Online, Vol. 61, Issue 12 https://doi.org/10.1107/S1600536805035592	journal	November 2005