Berislav Perić

Berislav Perić
Ruđer Bošković Institute | RBI · Division of Materials Chemistry

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53
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Publications

Publications (53)
Article
Full-text available
Ferrocene derivatives with mono- (8a–c) and bis-1,2,3-triazolyl (9 and 10a–13c) chelating groups were synthesized by regioselective copper(I)-catalysed 1,3-dipolar cycloaddition of terminal alkynes with ferrocene azides. Metal complexes of the ligands were prepared with Cu(II) and Zn(II) salts. Crystal structures of ligands 9 and 11a were determine...
Article
Amides are common molecules which are most often prepared using benzotriazole oxide coupling reagents. Such amides can be derivatised with compounds that contain a triple carbon-carbon bond in order to...
Article
The crystal structure of tris[dimethyl 5-({1-[(pyridin-2-yl-κ N )carbamoyl-κ O ]ethyl}carbamoyl)benzene-1,3-dicarboxylate]zinc(II) dinitrate acetonitrile trisolvate, [Zn(C 19 H 19 N 3 O 6 ) 3 ](NO 3 ) 2 ·3CH 3 CN or [Zn( L ) 3 ](NO 3 ) 2 ·3CH 3 CN, ( 1 ), has been determined by single-crystal X-ray diffraction. The neutral ligand L coordinates to t...
Article
Full-text available
Heme and nonheme-type flavone synthase enzymes, FS I and FS II are responsible for the synthesis of flavones, which play an important role in various biological processes, and have a wide range of biomedicinal properties including antitumor, antimalarial, and antioxidant activities. To get more insight into the mechanism of this curious enzyme reac...
Article
We present a double-stranded ferrocene pseudopeptide 2b which exhibits stimuli responsive chirality inversion triggered by solvent exchange or acid addition. Compound 2b exists as a mixture of self-assembled fast exchanging oligomers which macroscopically behave as a chiroptical switch with two stable states. The ferrocene group inversion results i...
Article
p-Disubstituted phenyldiketopiperazines 1 (R = H), 2 (R = NO2) and 3 (R = -N(CH3)2) were synthesized and characterized by NMR in solution and IR spectroscopy. The identity of the compounds was confirmed and their fragmentation analyzed by ESI-MS and HRMS spectrometry. X-ray single crystal structures revealed that the three compounds crystallize in...
Article
Three novel structures of 9,10-anthracene amino acid conjugates have been determined by combination of single crystal and powder X-ray diffraction measurements, pseudopotential plane wave DFT optimizations and ¹³C solid state NMR spectroscopy, including GIPAW calculation of the NMR parameters. All three structures show anti-conformation of amino ac...
Article
Chelating 1,4-disubstituted mono- (8a−8d) and bis-1,2,3-triazole-based (9a−11a) ligands were prepared by regioselective copper(I)-catalysed 1,3-dipolar cycloaddition of terminal alkynes with aromatic azides, together with bioconjugate 13a synthesized by amide coupling of L-phenylalanine methyl ester to 11a. Cu(II) and Zn(II) complexes were prepared...
Preprint
Chelating 1,4-disubstituted mono- (8a−8d) and bis-1,2,3-triazole-based (9a−11a) ligands were prepared by regioselective copper(I)-catalysed 1,3-dipolar cycloaddition of terminal alkynes with aromatic azides, together with bioconjugate 13a synthesized by amide coupling of L-phenylalanine methyl ester to 11a. Cu(II) and Zn(II) complexes were prepared...
Preprint
Chelating 1,4-disubstituted mono- (8a−8d) and bis-1,2,3-triazole-based (9a−11a) ligands were prepared by regioselective copper(I)-catalysed 1,3-dipolar cycloaddition of terminal alkynes with aromatic azides, together with bioconjugate 13a synthesized by amide coupling of L-phenylalanine methyl ester to 11a. Cu(II) and Zn(II) complexes were prepared...
Article
A variety of structurally different complexes of the isopropyl-bis(2-picolyl)amine (iPr-bpa) ligand were prepared with ZnA2 and CuA2 salts (A = Br─, Br─/PF6─, BF4─/F─, ClO4─). The choice of different counterion affected the stoichiometry, coordination number, geometry and formation of geometrical isomers. Crystal structures of four Zn(II) complexes...
Article
Metal complexes of iminodiacetamide (imda) ligands and metal ions Zn(II), Cu(II), Ni(II), and Co(II) were prepared using eight imda ligands (L1-L8) substituted with groups of different steric and electronic properties on the central amine N atom (H atom, methyl, isopropyl, and benzyl) and the para position of the phenyl rings (nitro and dimethylami...
Article
Full-text available
The Cover Feature shows a supramolecular catalytic system, envisioned as a factory machine. The worker uses a chiral cyclohexane to control the chirality in the remote rhodium machine head which does the selective hydrogenation reaction. The transfer of chirality is achieved by stacked phenyl‐phosphine gears shown in the insides of the machine. The...
Article
Full-text available
This work aims at studying the influence of structural parameters on computations of the ⁹³Nb quadrupolar interaction and chemical shift parameters in various niobates using first-principles approaches. We demonstrate that some of the computed NMR parameters, especially the isotropic chemical shift and the quadrupolar coupling constant, may differ...
Article
This work aims at studying the influence of structural parameters on computations of the 93Nb quadrupolar interaction and chemical shift parameters in various niobates using first-principles approaches. We demonstrate that some of the computed NMR parameters, especially the isotropic chemical shift and the quadrupolar coupling constant, may differ...
Article
This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine‐tuning the steric and/or electronic properties. Cis square‐planar metal complexes of Rh(I) and Pt(II)...
Article
Full-text available
Triphenyphosphine amino acid bioconjugates Ph2P-pC6H4-Aaa-OR, Aa = glycine (1G), alanine (2A), valine (3V), isoleucine (4I), proline (5P) or phenylalanine (6F), have been synthesized and used as monodentate ligands for the preparation of twelve metal complexes, [MCl2(Lig)2], M = Pd(II) or Pt(II). All prepared compounds were characterized by spectro...
Article
Non-covalent self-assembled chiral alanyl aminopyridine ligand exhibits supramolecular chirality in solution, independent of the organic solvent used. The supramolecular chirality of the assemblies is completely inverted by complexation to zinc ions. Up to now, such supramolecular metal-ligand system has not been reported in the literature.
Article
Full-text available
This paper describes the synthesis of an amide based conjugate of ferrocene (Fc), ethylenediamine (eda) and iminodiacetamide (imda), Fc-eda-imda (2). The compound (2) is characterized by various spectroscopic, crystallographic and thermoanalytical techniques in solid state and in solution. By crystallization of the title compound 2 from methanol or...
Article
Two hexanuclear niobium halide cluster compounds with a [Nb6×12]2+ (X=Cl, Br) diamagnetic cluster core, have been studied by a combination of experimental solid-state NMR/NQR techniques and PAW/GIPAW calculations. For niobium sites the NMR parameters were determined by using variable Bo field static broadband NMR measurements and additional NQR mea...
Article
Full-text available
Pseudo-peptide Me2N-pC6H4C(O)-Phe-OEt (1) exhibits two polymorphic forms which crystallizes in non-centrosymmetric space groups, monoclinic 1m (P21) and orthorhombic 1o (P212121). Both forms occur concomitantly or as a pure phase depending on the solvent of crystallization. Single crystal X-ray diffraction revealed equivalent two-dimensional layers...
Article
Full-text available
The influences of an oxygen ligand on the structural, magnetic and electronic properties of octahedral niobium cluster-based oxides and oxychlorides are reported. The Nb6 metal cluster is edge-bridged by twelve inner ligands and additionally bonded to six apical ligands to form Nb6Li 2La6 units (L = Cl, O) wherein oxygen and chlorine are perfectly...
Article
Magnetic interactions in solid-state tantalum cluster compounds have been evidenced by using magnetic susceptibility measurements and corroborated by broken-symmetry DFT calculations. The three selected compounds are based on [Ta(6)X(12)(H(2)O)(6)](3+) (X=Cl or/and Br) units with edge-bridged Ta(6) octahedral clusters. Although two of them crystall...
Article
The novel title compound, [(CH3)(4)N](2)[Ta6Br12(H2O)(6)]Br-4.-2H(2)O, with a [Ta6Br12](2+) cluster unit, has been prepared and structurally characterized. The compound crystallizes in space group C2/c, with a twofold axis passing through the cluster and the centre of symmetry located between the clusters. The nearest neighbouring cluster units are...
Article
The compound [Ni(RPOEt)2(C2H5OH)2](ClO4)2 (1) [RPOEt = bis{(diphenylphosphinyl)methyl}ethyl phosphinate] has been prepared in the form of single crystals and characterized by elemental and thermal analyses, IR spectroscopy and by a single crystal X-ray diffraction study. The complex crystallizes in the triclinic $ P\bar{1} $ space group with a =...
Article
The compound [NH4][(CH3)2NH2]2[Ta(C2O4)4]·2H2O has been synthesized and characterized by elemental and TG/DTA analyses, IR spectroscopy and by the single-crystal X-ray diffraction study. The structure comprises the [Ta(C2O4)4]3− anion, NH4+ and [(CH3)2NH2]+ cations and crystallization water molecules. The Ta atom is octacoordinated by oxygen atoms...
Article
A new hexanuclear cluster compound, [Et4N][Ta6Br12(H2O)6]Br4·4H2O (Et=ethyl) (1), with the paramagnetic [Ta6Br12]3+ cluster entity, was synthesized and characterized by elemental and TG/DTA analyses, IR and UV/Vis spectroscopy and by a single-crystal X-ray diffraction study. The presence of the paramagnetic [Ta6Br12]3+ unit was confirmed also by th...
Article
Magnetic properties of single crystals of the heterometallic complex [Cu(bpy)3]2[Cr(C2O4)3]NO3·9H2O (bpy = 2,2′-bipyridine) have been investigated. From the recorded EPR spectra, the spin-Hamiltonian parameters have been determined. The magnetization measurements have shown magnetic anisotropy at low temperatures, which has been analysed as a resul...
Article
Solvatomorphism has been found between two series of complexes of the composition [M(bpy)3]2[NbO(C2O4)3]Cl.nH2O [M = Fe2+ (1, 2), Co2+ (3, 4), Ni2+ (5, 6), Cu2+ (7) and Zn2+ (8, 9); bpy = 2,2'-bipyridine)], crystallizing in the monoclinic space group P2 1/c [3, 5, 8 (n = 11)] or in the orthorhombic space group P21 21 21 [2, 4, 6, 7 (n = 12)]. All t...
Article
Two novel compounds of the formulae [{Cu(phen)2}2(μ-C2O4)][Cu(phen)2(μ-C2O4)NbO(C2O4)2]2 · 8H2O (1) and [{Cu(bpy)2}2(μ-C2O4)][Cu(bpy)2(μ-C2O4)NbO(C2O4)2]2 · 0.5bpy · 7H2O (2) (phen = 1,10-phenanthroline, bpy = 2,2′-bipyridine) have been prepared and characterized by single crystal X-ray diffraction, IR spectroscopy and magnetic susceptibility measu...
Article
The compound Rb3[NbO(C2O4)3]⋅2H2O (1) has been synthesized by two different methods and its exact chemical composition established. The niobium atom is heptacoordinated by oxygen atoms forming a distorted pentagonal bipyramid. Inspite of some similarities, the structure of 1 is not isotypic with the structure of (NH4)3[NbO(C2O4)3]⋅H2O.
Article
By partial oxidation of a solution of (Ta6Cl12)Cl2·6 EtOH in n-butyl cyanide (n-BuCN) reddish crystals of the title compound were formed. The compound crystallizes in the monoclinic C2/m space group. The double salt components [(Ta6Cl12)Cl3(n-BuCN)3] and [(Ta6Cl12)Cl4(n-BuCN)2] are of Cs and C2h symmetry, respectively. The structure consists of lay...
Article
The synthesis and crystal structure of the mononuclear title compound, [Co(C(2)O(4))(C(10)H(8)N(2))(2)].5H(2)O, is reported. The Co atom is six-coordinated by two O atoms of a bidentate oxalate group and by four N atoms of two bipyridine ligands. The neutral [Co(C(2)O(4))(C(10)H(8)N(2))(2)] entities are connected by pi-pi stacking interactions of t...
Article
To compare the structural properties of oxalamide and thiooxalamide groups in the formation of hydrogen bonds suitable for supramolecular assemblies a series of retropeptides was studied. Some of them, having oxalamide bridges, are gelators of organic solvents and water. However, retropeptides with oxygen replaced by the sp(2) sulfur have not exhib...
Article
Comparative studies based on x-ray crystallography and NMR spectroscopy were used for structural characterization of the novel minor, imidazolidinone moiety containing, product 2b of the Maillard reaction obtained in vitro by using the galactose-modified endogenous opioid pentapeptide leucine-enkephalin (Tyr-Gly-Gly-Phe-Leu) 1. The x-ray analysis u...
Article
The title compound, [Ta(6)Br(12)(H(2)O)(6)](Br(0.4)Cl(1.6)) x 8H(2)O, crystallizes in space group P 1 macro. The structure contains two crystallographically independent [Ta(6)Br(12)(H(2)O)(6)](2+) cluster cations forming distinct layers parallel to the ab plane. The compound is isoconfigurational with the double salts [Ta(6)Br(12)(H(2)O)(6)]X(2) x...
Article
Full-text available
The novel title compound, [(CH(3))(4)N](2)[Ta(6)Br(12)(H(2)O)(6)]Br(4) x 2H(2)O, with a [Ta(6)Br(12)]2+ cluster unit, has been prepared and structurally characterized. The compound crystallizes in space group C2/c, with a twofold axis passing through the cluster and the centre of symmetry located between the clusters. The nearest neighbouring clust...
Article
Full-text available
The molecule of benzene-1,4-dicarboxamidine or benzdiamidine, C(8)H(10)N(4), reveals C(i) symmetry. Hydrogen bonds utilize the amino groups as double donors, whereas the imino groups act as double acceptors. The network formed is similar to that observed in the crystal packing of terephthalamide.
Article
Bis(LeuOH) (1a), bis-(ValOH) (2a) and bis(PhgOH) (5a) (Phg denotes (R)-phenylglycine) oxalyl amides are efficient low molecular weight organic gelators of various organic solvents and their mixtures as well as water, water/DMSO, and water/DMF mixtures. The organisational motifs in aqueous gels are dominated primarily by lipophilic interactions whil...
Article
Aroylhydrazones derived from salicylaldehyde, o-vanillin and nicotinic acid hydrazide have been synthesized and characterized on the basis of NMR, IR and UV/Vis spectral data. The crystal and molecular structure of N′-salicylidene-3-pyridinecarbohydrazide has been determined by X-ray diffraction.
Article
The title compound, 2,2'-(oxalyldiimino)bis(3-methylbutanoic acid), C12H20N2O6, possesses a centre of symmetry. In the crystal, molecules are connected by hydrogen bonds between oxamide and carboxyl groups, similar to the pattern of the monoclinic forms of HO-Gly-CO-CO-Gly-OH and HO-Aib-CO-CO-Aib-OH (Gly is glycine and Aib is 2-aminoisobutyric acid...
Article
Full-text available
In the title compound, C20H22N4O4*C2H6OS, two distinct hydrogen-bond systems connect oxalamide groups in one pattern and primary amide groups in the other to form a two-dimensional network perpendicular to the c axis. These hydrophilic layers are joined to the three-dimensional structure through C--H...pi interactions. The hydrogen-bonded waved lay...
Article
Full-text available
The title compound, 2,2′-(oxalyldiimino)bis(3-methylbutanoic acid), C12H20N2O6, possesses a centre of symmetry. In the crystal, mol­ecules are connected by hydrogen bonds between ox­amide and carboxyl groups, similar to the pattern of the monoclinic forms of HO–Gly–CO–CO–Gly–OH and HO–Aib–CO–CO–Aib–OH (Gly is glycine and Aib is 2-amino­isobutyric a...
Article
The structure of 4,40-dibromobenzophenone, C13H8Br2O, was determined at two different temperatures (293 and 103 K). A phase transition was not detected in this temperature range. Its crystal structure was found to be isostructural with that of the diiodo analogue, but not with the structure of the dichloro derivative.
Article
The structure of 4,4′-di­bromo­benzo­phenone, C13H8Br2O, was determined at two different temperatures (293 and 103 K). A phase transition was not detected in this temperature range. Its crystal structure was found to be isostructural with that of the di­iodo analogue, but not with the structure of the di­chloro derivative.
Article
Acid-catalyzed methanolysis of N-hydroxy-a-oxobenzeneethanimidoyl chloride (1), a 2-(hydroxyimino)-1- phenylethan-1-one derivative obtained in one step from acetophenone, leads to a constant ratio of methyl a-oxobenzeneacetate (2) and methyl a-(hydroxyimino)benzeneacetate (3). 13C(a) Labelled [13C]-1 affords 13C(a) labelled [13C]-3, thus discarding...
Article
Acid-catalyzed methanolysis of PhCOCClNOH, obtained in 1 step from PhAc, leads to a const. ratio of PhCOCO2Me and PhC(NOH)CO2Me. Ph13COCClNOH, affords Ph13C(NOH)CO2Me, thus discarding the hypothesis of its formation via 1,2-arene migration. The reported sequence opens a novel approach to phenylglyoxylates and mandelates from PhAc. The mol. structur...
Article
The properties of the vanadium valence band have been studied by normal emission ultraviolet photoelectron spectroscopy from V(100) surface by the use of different photon energies (21.2, 16.8 and 11.8 eV). The bottom of the d-band at the high symmetry point H12 was found to be around 2.5 eV. We did not find conclusive evidence for the existence of...

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Project
This project aims at the development of chiral transition metal catalysts with particular emphasis on inspiration taken from nature. A beta-turn structure is proposed as key feature of chiral catalysts that resemble artificial enzymes with a minimal but functional outer-coordination sphere. These minimal artificial enzymes could find applications in asymmetric synthesis of drugs or drug intermediates produced by pharmaceutical industry. In asymmetric catalysis it is well established that the chiral information should be incorporated as close as possible to the coordination sphere of the catalytic metal. We challenge this important principle and use a catalytic metal center that is only prochiral. The chirality is transmitted by "backdoor induction" via hydrogen bonding of distant pendant amino acids that represent the outer-coordination sphere. Preliminary results provide a proof of concept and strongly indicate that simple amino acid bioconjugates of monodentate triphenylphosphane ligands can form supramolecular L2M complexes with Rh(I) that selectively catalyze a model asymmetric hydrogenation reaction with major impact of the distant amino acid sequence on selectivity [Kirin and Kokan, RSC Adv. 2012, Eur. J. Org. Chem. 2013 and Organometallics 2014; ee’s up to 84 %]. Within this project, a significant extension is proposed including (i) the use of new ligand bioconjugates with phosphorous or nitrogen donor atoms, (ii) the use of new substrates and (iii) the use of other transition metals for different asymmetric reactions, namely Ru(II)-catalyzed hydrogenation, Pd(II)-catalyzed alkylation and Ln(III) catalyzed silylcyanation.