Abstract:S SGold Substrate where R 1 , R 2 = H, methyl, phenyl, 1-naphthyl, or R 1 -R 2 = (un)substituted cyclohexylThe synthesis and stereochemistry of a series of new cyclic disulfides containing (poly)spirane 1,2-dithiolane units are reported. Also included is a study of the self-assembled monolayers (SAMs) of these compounds on a gold surface. The characteristics of the resultant SAMs were determined by IR spectroscopy using molecular mechanics calculations.
“… Synthesis of compound A : ( i ) toluene/acetone, H 3 PO 4 , reflux, 16 h15 ( ii ) EtOH, Na 2 S 2 , reflux, 4 h14 ( iii ) EtOH/H 2 O, HCl, room temperature, 24 h. The detailed procedure of step ( iii ) is presented in the Experimental Section. …”
Section: Resultsmentioning
confidence: 99%
“…Treatment of Fe 3 (CO) 12 with compound A [14] or B [15] in toluene at 100 °C for one hour followed by column chromatography afforded complexes 1 and 2 in 45 % and 41 % yields, respectively (Scheme 1). We synthesized compound A according to Scheme 2.…”
FeFe] hydrogenase model complexes [Fe(CO) 3 ] 2 [(μ-ECH 2 ) 2 C(CH 2 OH) 2 ] (E = S (1) or Se (2)) containing CH 2 OH bridgehead substituents were synthesized via reaction of equimolar amounts of 4,4-bis(hydroxymethyl)-1,2-dithiolane (A) or 4,4-bis(hydroxymethyl)-1,2-diselenolane (B) with Fe 3 (CO) 12 in toluene at 100°C.
“… Synthesis of compound A : ( i ) toluene/acetone, H 3 PO 4 , reflux, 16 h15 ( ii ) EtOH, Na 2 S 2 , reflux, 4 h14 ( iii ) EtOH/H 2 O, HCl, room temperature, 24 h. The detailed procedure of step ( iii ) is presented in the Experimental Section. …”
Section: Resultsmentioning
confidence: 99%
“…Treatment of Fe 3 (CO) 12 with compound A [14] or B [15] in toluene at 100 °C for one hour followed by column chromatography afforded complexes 1 and 2 in 45 % and 41 % yields, respectively (Scheme 1). We synthesized compound A according to Scheme 2.…”
FeFe] hydrogenase model complexes [Fe(CO) 3 ] 2 [(μ-ECH 2 ) 2 C(CH 2 OH) 2 ] (E = S (1) or Se (2)) containing CH 2 OH bridgehead substituents were synthesized via reaction of equimolar amounts of 4,4-bis(hydroxymethyl)-1,2-dithiolane (A) or 4,4-bis(hydroxymethyl)-1,2-diselenolane (B) with Fe 3 (CO) 12 in toluene at 100°C.
Four diiron hexacarbonyl-complexes containing dithiolato (5), diselenolato (6), selenolato-thiolato (7) and μ2,κ3-C,O,Se-ligands (8), respectively have been prepared as [FeFe]-hydrogenase mimics.
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