Online citations, reference lists, and bibliographies.
← Back to Search

The Redox Behaviour Of Ferrocenyl Alcohols And Ferrocenediyl-diols: Crystal And Molecular Structure Of Ferrocenyl(2-furyl) Phenylmethanol☆

G. Ferguson, C. Glidewell, G. Opromolla, C. M. Zakaria, P. Zanello
Published 1996 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Abstract Cyclic voltammetry and controlled-potential coulometry show that ferrocenyl alcohols of type (C5H5)Fe(C5H4)C(OH)RR′ and ferrocenediols of type Fe[(C5H4)CCR′(OH)]2 undergo quantitative and reversible one-electron oxidation at the metal centre, and that the redox potentials are controlled predominantly by the inductive effects of the substituents at the α-carbon. The crystal structure of the new alcohol ferrocenyl(2-furyl)phenylmethanol not only confirms its molecular constitution, but also demonstrates that in the solid state it forms centrosymmetric hydrogen-bonded dimers involving cyclic (OH)2 bridge without any participation of the furan oxygen atom in the hydrogen bonding.
This paper references
10.1016/0022-328X(88)80168-2
The electronic structure of di-η5-cyclopentadienyliron(II) derivatives
A. M. Al-Saeed (1988)
10.1016/0022-328X(68)80053-1
Beziehungen zwischen polarographischem und spektralem verhalten einiger substituierter ferrocene
H. Hennig (1968)
10.1016/0022-328X(94)87015-2
Hydrogen bonding in ferrocene derivatives: Crystal structure of racemic ferrocenyl(phenyl)methanol
G. Ferguson (1994)
10.1016/0022-328X(91)86433-Q
Redox potential and substituent effects at ferrocene derivatives. Estimates of Hammett σp and taft polar σ substituent constants
M. Emilia (1991)
Photochemical reactions of harmalol. II. Electronic spectra
M. C. Biondic (1993)
10.1016/0013-4686(89)80016-7
Cyclic voltammetry of some ferrocenephanes in non-aqueous solvents—II. Solvent effects☆
H. Scholl (1989)
10.1021/JA01507A011
Chronopotentiometric Studies on the Oxidation of Ferrocene, Ruthenocene, Osmocene and Some of their Derivatives1
T. Kuwana (1960)
10.1039/DT98900000S1
Supplement. Tables of bond lengths determined by X-ray and neutron diffraction. Part 2. Organometallic compounds and co-ordination complexes of the d- and f-block metals
A. Orpen (1989)
10.1107/S0108270193007164
O-H...π(arene) intermolecular hydrogen bonding in the structure of 1,1,2-triphenylethanol
G. Ferguson (1994)
10.1021/AR00172A005
Encoding and decoding hydrogen-bond patterns of organic compounds
M. C. Etter (1990)
10.1039/P298700000S1
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
F. Allen (1987)
10.1016/0022-328X(95)05720-A
Redox behaviour of ferrocene derivatives VIII. 1,1′-Bis(diphenylphosphino)ferrocenes
P. Zanello (1996)
10.1039/P19770000887
High-yield syntheses of dilithio-derivatives of furan, thiophen, N-methylpyrrole, 3-methylfuran, and 3-methylthiophen. Application of the method to 2-methylfuran, 2-methylthiophen, 2,5-dimethylfuran, 2,5-dimethylthiophen, benzo[b]furan, benzo[b]thiophen, pyrrole, and indole
D. J. Chadwick (1977)
10.1107/S0021889889003201
NRCVAX ― an interactive-program system for structure analysis
E. Gabe (1989)
10.1021/ja00451a019
Intervalence transfer in substituted biferrocene cations
Carole LeVanda (1977)
10.1107/S0108768194013984
Hydrogen bonding in diphenylmethanols, RCPh2OH: structures of monomeric (4-biphenyl)diphenylmethanol and diphenyl(2-pyridyl)methanol, dimeric 1,1,3-triphenylpropyn-1-ol, trimeric 2-methyl-1,1-diphenylpropan-1-ol, tetrameric diphenyl(2-thienyl)methanol, hexameric bis(pentafluorophenyl)methanol (at 29
G. Ferguson (1995)
10.1021/CR00002A004
A survey of Hammett substituent constants and resonance and field parameters
C. Hansch (1991)
10.1016/0022-328X(92)88016-C
The reaction between ferrocenyllithium and trimethylacetylchloride to form either trimethylacetylferrocene or 1,1′-bis(ferrocenyl)-2,2′-dimethylpro
H. Sharma (1992)
10.1021/IC50218A062
Determination of E20-E10 in multistep charge transfer by stationary-electrode pulse and cyclic voltammetry: application to binuclear ruthenium ammines
D. Richardson (1981)
10.1021/OM00151A020
Bridged ferrocenes. 13. Preparation and properties of derivatives with .beta.-oxatrimethylene bridges
M. Hillman (1987)
10.1021/JA00510A023
Binuclear complexes of macrocyclic ligands: electrochemical and spectral properties of homobinuclear Cu/sup II/Cu/sup II/, Cu/sup II/Cu/sup I/, and Cu/sup I/Cu/sup I/ species including an estimated intramolecular electron transfer rate
R. R. Gagne (1979)
10.1021/OM00016A027
1,1'-Disubstituted Ferrocenes as Donors for Charge-Transfer Complexes. Synthesis, Structure, Conductivity, and Magnetic Properties
A. Togni (1994)
10.1107/S0108270192011715
Structures of 1-ferrocenyl-1-phenylethanol, ferrocenyl(diphenyl)methanol and ferrocene-1,1'-diylbis(diphenylmethanol)
G. Ferguson (1993)
10.1107/S0108768189012929
Graph-set analysis of hydrogen-bond patterns in organic crystals.
M. C. Etter (1990)



This paper is referenced by
10.1016/J.JORGANCHEM.2003.10.010
Synthesis, structures and reactions of some metallocene alcohols
T. J. Brunker (2004)
10.1007/BF02256754
Furan derivatives of group VIII elements (review)
E. Lukevics (1997)
10.1016/S0022-328X(01)00915-9
An investigation of the chemistry of ferrocenoyl derivatives. The synthesis and reactions of ferrocenoyl imidazolide and its derivatives
C. Imrie (2001)
10.1016/S0022-328X(00)00075-9
Oxidation potential of benzylferrocenes and related compounds: effects of the ortho-methoxy substituent in the phenyl group
M. Asahara (2000)
10.3184/174751914X14099355662182
Efficient Synthesis of α-Ferrocenyl Tertiary Alcohols Via CeCl3-Promoted Addition of Grignard Reagents to Large Hindered Ketones
H. Zhao (2014)
10.1016/0022-328X(96)06199-2
The redox behaviour of some bis-ferrocenyl compounds: crystal and molecular structures of diferrocenylmethane and diferrocenylmethanol
G. Ferguson (1996)
10.1016/J.JORGANCHEM.2018.02.006
From ferrocenyl selenoesters to diferrocenyl methanols
Deeb Taher (2018)
10.1039/C5RA01545F
An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)methanethione
D. Kumar (2015)
10.1016/S0022-328X(97)00133-2
Functionalized pentamethylferrocenes: Synthesis, structure, and electrochemistry
B. Bildstein (1997)
10.1002/ZAAC.200700391
Cyclopentadienyl Tantalum(V) Complexes with Primary and Secondary Ferrocenylphosphine Ligands
René Kalio (2007)
10.1002/chem.201802364
Electrochemical, Spectroelectrochemical, Mößbauer, and EPR Spectroscopic Studies on Ferrocenyl-Substituted Tritylium Dyes.
S. Oßwald (2018)
Semantic Scholar Logo Some data provided by SemanticScholar