Steven R. Alley

Dublin City University, Dublin, L, Ireland

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Publications (14)6.33 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: The neutral diethyl 4,4'-(ferrocene-1,1'-diyl)dibenzoate, Fe[eta(5)-(C(5)H(4))(4-C(6)H(4)CO(2)Et)](2) (I), yields (II) (following base hydrolysis) as the unusual complex salt poly[disodium bis[diethyl 4,4'-(ferrocene-1,1'-diyl)dibenzoate] 0.6-hydrate] or [Na(+)](2)[Fe{eta(5)-(C(5)H(4))-4-C(6)H(4)CO(2)(-)}(2)].0.6H(2)O with Z' = 5. Compound (I) crystallizes in the triclinic system, space group P1, with two molecules having similar geometry in the asymmetric unit (Z' = 2). The salt complex (II) crystallizes in the orthorhombic system, space group Pbca, with the asymmetric unit comprising poly[decasodium pentakis[diethyl 4,4'-(ferrocene-1,1'-diyl)dibenzoate] trihydrate] or [Na(+)](10)[Fe{eta(5)-(C(5)H(4))-4-C(6)H(4)CO(2)(-)}(2)](5).3H(2)O. The five independent 1,1'-Fc[(4-C(6)H(4)CO(2))(-)](2) dianions stack in an offset ladder (stepped) arrangement with the ten benzoates mutually oriented cisoid towards and bonded to a central layer comprising the ten Na(+) ions and three water molecules [1,1'-Fc = eta(5)-(C(5)H(4))(2)Fe]. The five dianions differ in the cisoid orientations of their pendant benzoate groups, with four having their -C(6)H(4)- groups mutually oriented at interplanar angles from 0.6 (3) to 3.2 (3) degrees (as pi...pi stacked C(6) rings) and interacting principally with Na(+) ions. The fifth dianion is distorted and opens up to an unprecedented -C(6)H(4)- interplanar angle of 18.6 (3) degrees through bending of the two 4-C(6)H(4)CO(2) groups and with several ionic interactions involving the three water molecules (arranged as one-dimensional zigzag chains in the lattice). Overall packing comprises two-dimensional layers of Na(+) cations coordinated mainly by the carboxylate O atoms, and one-dimensional water chains. The non-polar Fc(C(6)H(4))(2) groups are arranged perpendicular to the layers and mutually interlock through a series of efficient C-H...pi stacking contacts in a herringbone fashion to produce an overall segregation of polar and non-polar entities.
    Acta crystallographica. Section B, Structural science 04/2010; 66(Pt 2):196-205. · 1.80 Impact Factor
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    ABSTRACT: The title compound, [Fe(C5H5)(C18H15N2O)], a product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-6-methylpyridine, crystallizes with two dissimilar molecules in the asymmetric unit. In one molecule, the picoline amide group is directed away from the 2-ferrocenylbenzene moiety (anti) whereas in the other, these are proximate (syn). In the crystal structure, molecules aggregate into dimers via cyclic, asymmetric N-H...N interactions with graph set R22(8), and are further augmented via intramolecular C-H...O=C and interdimer C-H...[pi](arene) interactions. Dimers are linked into chains along the [102] direction via weak C-H...O hydrogen bonds.
    Acta Crystallographica Section E Structure Reports Online 01/2010; · 0.35 Impact Factor
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    ABSTRACT: The title compound, [Fe(C(5)H(5))(C(18)H(15)N(2)O)], a product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-6-methyl-pyridine, crystallizes with two dissimilar mol-ecules in the asymmetric unit. In one mol-ecule, the picoline amide group is directed away from the 2-ferrocenylbenzene moiety (anti) whereas in the other, these are proximate (syn). In the crystal structure, mol-ecules aggregate into dimers via cyclic, asymmetric N-H⋯N inter-actions with graph set R(2) (2)(8), and are further augmented via intra-molecular C-H⋯O=C and inter-dimer C-H⋯π(arene) inter-actions. Dimers are linked into chains along the [102] direction via weak C-H⋯O hydrogen bonds.
    Acta Crystallographica Section E Structure Reports Online 01/2010; 66(Pt 4):m396. · 0.35 Impact Factor
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    ABSTRACT: The title compound, [Fe(2)(C(5)H(5))(2)(C(30)H(22)N(2)O(2))], a 2:1 product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-4-methyl-pyridine, forms a twisted mol-ecular structure in the solid state due to steric effects from the two benzene rings ortho-substituted with ferrocenyl and carbonyl-derived groups. A short intra-molecular C-H⋯π interaction is observed involving a substituted η(5)-C(5)H(4) ring and an ortho H atom of the benzene ring on the opposite side of the mol-ecule. In the crystal structure, there are no classical hydrogen bonds: inter-actions comprise a short C(6)-H⋯π(C(6)) inter-action involving substituted benzene rings and two C-H⋯O=C inter-actions per mol-ecule.
    Acta Crystallographica Section E Structure Reports Online 01/2009; 65(Pt 3):m332-3. · 0.35 Impact Factor
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    ABSTRACT: The title compound, [Fe2(C5H5)2(C30H22N2O2)], a 2:1 product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-4-methylpyridine, forms a twisted molecular structure in the solid state due to steric effects from the two benzene rings ortho-substituted with ferrocenyl and carbonyl-derived groups. A short intramolecular C-H...[pi] interaction is observed involving a substituted [eta]5-C5H4 ring and an ortho H atom of the benzene ring on the opposite side of the molecule. In the crystal structure, there are no classical hydrogen bonds: interactions comprise a short C6-H...[pi](C6) interaction involving substituted benzene rings and two C-H...O=C interactions per molecule.
    Acta Crystallographica Section E Structure Reports Online 01/2009; · 0.35 Impact Factor
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    ABSTRACT: N-ortho-ferrocenyl benzoyl dipeptide esters 2–6 were prepared by coupling ortho-ferrocenyl benzoic acid 1 to the dipeptide ethyl esters GlyGly(OEt) (2), GlyAla(OEt) (3), GlyPhe(OEt) (4), AlaGly(OEt) (5) and AlaPhe(OEt) (6). The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry and cyclic voltammetry. The cytotoxicity of 3 and 5 towards lung cancer cells has been determined.
    Journal of Organometallic Chemistry - J ORGANOMET CHEM. 01/2007; 692(6):1405-1410.
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    ABSTRACT: A series of N-meta-ferrocenyl benzoyl dipeptide esters 2–5 have been prepared by coupling meta-ferrocenyl benzoic acid 1b to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed in the synthesis were AlaGly(OEt) (2), AlaAla(OEt) (3), AlaLeu(OEt) (4) and AlaPhe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry (MALDI-MS, ESI-MS), and cyclic voltammetry (CV). In addition, the X-ray crystal structure and cytotoxicity of N-{meta-(ferrocenyl)-benzoyl}-l-alanine-glycine ethyl ester (2) towards lung cancer cells has been determined.
    Journal of Organometallic Chemistry - J ORGANOMET CHEM. 01/2007; 692(6):1292-1299.
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    ABSTRACT: A series of novel N-meta-ferrocenyl benzoyl dipeptide esters (2–5) have been prepared by coupling meta-ferrocenyl benzoic acid (1) to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed were GlyGly(OEt) (2), GlyAla(OEt) (3), GlyLeu(OEt) (4) and GlyPhe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques and by mass spectrometry (MALDI-MS, ESI-MS).
    Inorganic Chemistry Communications - INORG CHEM COMMUN. 01/2006; 9(2):152-155.
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    ABSTRACT: A series of N-ortho-ferrocenyl benzoyl amino acid ethyl esters 3–9 have been prepared by coupling ortho-ferrocenyl benzoic acid 2 to the amino acid ethyl esters of glycine, l-alanine, l-leucine, l-phenylalanine, β-alanine, 4-aminobutyric acid and (±)-2-aminobutyric acid using the conventional 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole protocol. The compounds were fully characterized by a range of NMR spectroscopic techniques and by mass spectrometry (MALDI-MS, ESI-MS). The X-ray crystal structure of the l-phenylalanine derivative 6 has been determined.
    Journal of Organometallic Chemistry - J ORGANOMET CHEM. 01/2006; 691(3):463-469.
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    ABSTRACT: N-para-ferrocenyl benzoyl dipeptide esters 2–5 were prepared by coupling para-ferrocenyl benzoic acid 1 to the dipeptide ethyl esters GlyGly(OEt) 2, GlyAla(OEt) 3, GlyLeu(OEt) 4 and GlyPhe(OEt) 5. The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry (ESI-MS, FABMS, MS/MS) and cyclic voltammetry (CV). The a1 and b1 ions appeared at one mass unit less than the expected mass in the tandem mass spectra. The CV curves of compounds 2–5 exhibited quasi-reversible redox behavior similar to the Fc/Fc+ redox couple and displayed oxidation potential values in the 50–55mV range, against the Fc/Fc+ redox couple.
    Inorganic Chemistry Communications 01/2006; 9(12):1267-1270. · 2.02 Impact Factor
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    ABSTRACT: A series ofN-para-ferrocenyl benzoyl dipeptide esters 2–5 were prepared by coupling para-ferrocenyl benzoic acid (1) to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed in the synthesis were Ala-Gly(OEt) (2), Ala-Ala(OEt) (3), Ala-Leu(OEt) (4) and Ala-Phe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques, electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). In addition the X-ray crystal structure of the l-alanine-glycine derivative 2 has been determined.
    Journal of Organometallic Chemistry - J ORGANOMET CHEM. 01/2006; 691(22):4686-4693.
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    ABSTRACT: The conformations and hydrogen bonding in the thiophene and thiazole title compounds, [Fe(C5H5)(C20H14NO3S)], (I), and [Fe(C5H5)(C19H17N2O3S)], (II), are discussed. The sequence (C5H4)-(C6H4)-(CONH)-(C4H2S)-(CO2Me) of rings and moieties in (I) is close to being planar; all consecutive interplanar angles are less than 10 degrees . An intramolecular N-H...O=C(ester) hydrogen bond [graph set S6, N...O = 2.768 (2) A and N-H...O = 134 (2) degrees ] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular C(ar)-H...O=C(ester/amide) interactions along [010], with C...O distances ranging from 3.401 (3) to 3.577 (2) A. The thiazole system in (II) crystallizes with two molecules in the asymmetric unit; these differ in the conformation along their long molecular axes; for example, the interplanar angle between the phenylene (C6H4) and thiazole (C3NS) rings is 8.1 (2) degrees in one molecule and 27.66 (14) degrees in the other. Intermolecular N-H...O=C(ester) hydrogen bonds [N...O = 2.972 (4) and 2.971 (3) A], each augmented by a C(phenylene)-H...O=C(ester) interaction [3.184 (5) and 3.395 (4) A], form motifs with graph set R2(1)(7) and generate chains along [100]. The amide C=O groups do not participate in hydrogen bonding. Compound (II) is the first reported ferrocenyl-containing thiazole structure.
    Acta Crystallographica Section C Crystal Structure Communications 08/2005; 61(Pt 7):m365-9. · 0.78 Impact Factor
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    ABSTRACT: The title compound, [Fe(C₅H₅)(C₁₂H₁₀NO₃S)], was synthesized from ferrocenecarboxylic acid and methyl 2-aminothiophene-3-carboxylate in modest yield. The substituted ring system is essentially planar through the amidothienylcarboxylate moiety, η⁵-(C₅H₄)CONH(C₄H₂S)CO₂Me, with the amido unit at an angle of 3.60 (7)° to the five-atom thienyl group, which is oriented at an angle of 3.17 (7)° to the ester moiety. The primary hydrogen bond is an intramolecular N-H...O=Ccarboxylate interaction [N...O 2.727 (2) Å], and the main intermolecular hydrogen bond involves a thienyl carboxylate and the carboxylate of a symmetry-related molecule [C...O 3.443 (3) Å].
    Acta Crystallographica Section E Structure Reports Online 02/2005; · 0.35 Impact Factor
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    ABSTRACT: A series of N-meta-ferrocenyl benzoyl amino acid esters 3–10 have been prepared by coupling meta-ferrocenyl benzoic acid 2 to the amino acid esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The amino acids employed in the synthesis were glycine, l-alanine, l-leucine, l-phenylalanine, β-alanine, 4-aminobutyric acid, 2-aminobutyric acid and 2-aminoisobutyric acid. The compounds were fully characterized by a range of NMR spectroscopic techniques and mass spectrometry (MALDI-MS, ESI-MS).
    Inorganic Chemistry Communications - INORG CHEM COMMUN. 01/2005; 8(5):429-432.