Willem L. Driessen

Leiden University, Leyden, South Holland, Netherlands

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Publications (209)502.87 Total impact

  • Patrick Gamez, Peter G. Aubel, Willem L. Driessen, Jan Reedijk
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    ABSTRACT: The controlled oxidation of C–H bonds is one of the most challenging and difficult reactions in organic chemistry. Generally, it requires either stoichiometric amounts of toxic heavy metal salts or very expensive catalysts containing transition metals such as palladium, rhodium or ruthenium. The scientific community used to focus their investigations towards these relatively rare and costly elements while neglecting to look at how Nature performs these types of reactions. Biological systems only employ abundantly available metals like iron, zinc and copper. This review summarizes the background and the state of the art of enzymatic and biomimetic oxidation catalysts involving copper as the active metal center. Recent developments have shown the first very promising results in this incipient field.
    ChemInform 04/2010; 33(13). DOI:10.1002/chin.200213265
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    ABSTRACT: The novel didentate ligand 2-(3,5-dimethyl-1-pyrazolyl)ethylamine (Naed) and the tridentate ligand bis[2-(3,5-dimethyl-1-pyrazolyl)ethyl] amine (ddaH) were immobilized onto silica by two different methods. The first method involves the coupling of the ligand to silica, previously modified with (3-glycidyloxypropyl)trimethoxysilane (GLYMO). The second method involves the coupling of the ligand to the oxirane ring of GLYMO in a homogeneous reaction, followed by grafting onto silica, yielding the highest ligand concentrations on the silica (about 0.3 mmol/g silica). With the first method, only part of the epoxy group reacts with the ligand. With Naed, tertiary amines are also formed through reaction of the primary amine group of the ligand with two epoxy groups.These new ion-exchange materials selectively adsorb Cu2+ (maximum capacity 0.11–0.26 mmol Cu2+ per gram of ion exchange) at pH > 2 from aqueous solutions containing a mixture of the bivalent metal ions, Cu2+, Cd2+, Zn2+, Ni2+ and Co2+. For products containing the didentate ligand Naed as the chelating group, the metal-ion capacity decreases rapidly with decreasing pH, while the Cu2+ -uptake capacity for the product containing the tridentate ligand ddaH is comparatively high at low pH.
    01/2010; 111(9):371 - 378. DOI:10.1002/recl.19921110901
  • H.J. Hoorn, P. de Joode, W.L. Driessen, J. Reedijk
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    ABSTRACT: Four potentially tridentate bis(2-pyridylalkyl)amines, differing in the number of methylene groups in the alkyl chain, have been coupled to the epoxy-containing bifunctional spacer (3-glycidoxypropyl)trimethoxysilane (GLYMO) and subsequently grafted onto silica. These ion exchangers were characterized by solid-state CP-MAS 13C-NMR and elemental analyses. The obtained ligand concentrations varied from 0.29-0.63 mmol/g ion exchanger. With the only exception of Alfa-GLYMO-bis(2-pyridyl)amine, which showed a very low capacity for any of the metal ions tested, these ion-exchange materials selectively absorbed Cu2+, with a maximum capacity of 0.22-0.59 mmol/g ion exchanger at pH 5.6, from aqueous solutions containing a mixture of the divalent metal ions Cu2+, Ni2+, Co2+, Cd2+ and Zn2+. The metal-uptake capacities and distribution coefficients established at different pH, correlate with the length of the alkyl bridge in the chelating ligand. The longer the alkyl spacer the lower the capacity and the metal-ligand complex stability at lower pH. The use of strong chelating tridentate N-donor ligands greatly increases the ligand occupation by metal ions. The Cu2+ uptake varies strongly with pH in the case of Alfa-GLYMO-bis[2-(2-pyridyl) ethyl]amine.
    01/2010; 115(3):191 - 197. DOI:10.1002/recl.19961150306
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    ABSTRACT: Twenty-six new coordination compounds are reported with methyl formate, ethyl acetate and diethyl malonate as the ligands, viz. [M(HCOOCH3)62+] [FeCl4−]2, [M(HCOOCH3)62+] [InCl4−]2, [M(CH3COOC2H5)62+] [SbCl6−]2, and [M(CH2(COOC2H5)2)32+] [SbCl6−]2, where M is Mg(II), Mn(II), Fe(II), Co(II), Ni(II), and Zn(II), and for the ethyl acetate and diethyl malonate solvates M is also Ca(II).In the complexes the carbonyl stretching vibration is shifted to lower frequencies with regard to this vibration in the free ligands. The magnitudes of these shifts are dependent on the metal ions. Frequency-shifts of other ligand vibrations are also observed. When the shifts are dependent on the metal ions, the magnitudes of the shifts follow the Irving-Williams sequence.For the methyl formate and ethyl acetate solvates a metal-dependent absorption band appears in the far infrared, which is attributed to the metal-ligand stretching vibration. This band could not be located for the diethyl malonate solvates.Investigation of ligand field spectra indicates the presence of octahedral species M(O)62+ in the solid compounds. Values for Dq and B for the Co(II) and Ni(II) compounds are reported, and the ligands are placed in the spectro-chemical and nephelauxetic series.
    01/2010; 89(4):353 - 367. DOI:10.1002/recl.19700890403
  • W. L. Driessen, W. L. Groeneveld
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    ABSTRACT: A series of new complexes is reported with acetone as the ligand: viz. [M(CH3COCH3)62+][A−]2 where M is Mg(II), Ca(II), Sr(II), Mn(II), Fe(II), Co(II), Ni(II), and Zn(II); and A− is FeCl−4 and InCl−4.In the complexes, the carbonyl vibration is shifted to lower frequencies and the CO bending, the CO deformation, and the CCC deformation vibrations are shifted to higher frequencies with regard to the vibrations in the free ligand. The magnitudes of the shifts are dependent on the metal ions. In the far infrared a metal-dependent absorption band appears, which is attributed to the metal-ligand stretching vibration.Investigation of ligand field spectra indicates the presence of octahedral species M(acetone)62+ in the solid compounds. Values for Dq and B′ are reported and the ligand is placed in the spectrochemical and nephelauxetic series.
    01/2010; 88(8):977 - 988. DOI:10.1002/recl.19690880811
  • W. L. Driessen, W. L. Groeneveld
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    ABSTRACT: A series of new complexes is reported with phosphorus oxychloride as a ligand: viz., complexes of Mg(II), Ca(II), Sr(II), Mn(II), Co(II), Ni(II), Cu(II) and Zn(II). Reflection spectra in the visible and near infrared region indicate an octahedral configuration of the metal ion and the POCl3 molecules.
    01/2010; 87(7):786 - 794. DOI:10.1002/recl.19680870706
  • 01/2010; 91(10). DOI:10.1002/recl.19720911007
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    ABSTRACT: The didentate N,O donor ligand 1-(2-hydroxyethyl)-3,5-dimethylpyrazole (N-hed) renders two kinds of coordination compounds, viz. [M(N-hed)2(NO3)2] with M=Co, Ni, Cu, and Zn, [Ni(N-hed)2(NCS)2], and [Cu(N-hed)2Cl2] in which the ligand is neutral, and [Cu(N-oed)X]2 with X=Cl, Br, and NO3 in which the ligand N-hed is in its deprotonated form, viz. 1-(2-oxidoethyl)-3,5-dimethylpyrazole (N-oed).The crystal structure of [Cu(N-hed)2(NO3)2] shows it to be mononuclear, with the copper ion at a centre of symmetry. Monoclinic, space group P21/c, a = 7.8176(8), b = 14.93(2), c = 8.4076(8) Å, β = 92.62(2)°, Z = 2; R = 0.036 (Rw = 0.038) for 2132 significant reflections. The copper(II) ion is in a tetragonal-distorted, elongated-octahedral environment of two trans pyrazole nitrogen atoms at 1.974(2) Å, two trans hydroxyl oxygen atoms at 1.991(2) Å, and two trans oxygen atoms of monodentate coordinated nitrate anions at 2.561(2) Å. The structure is stabilized by strong intramolecular hydrogen bonds between the hydroxyl group of the coordinated ligand and an oxygen atom of the coordinated nitrate ion with a short O-O distance of 2.599(2) Å. The metal ions in the compounds [M(N-hed)2X2] are octahedrally surrounded by two nitrogen and two oxygen atoms of the ligand and by two anion donor atoms (respectively O, N, or Cl).The crystal structure of [Cu(N-oed)Br]2 shows it to be dinuclear. Triclinic, space group P2/1, a = 4.5213(6), b = 8.484(1), c = 13.052(7) Å, α = 81.50(3), β = 85.79(4), γ = 77.79(2)°, Z = 1, R = 0.148 (Rw = 0.224) for 1534 reflections. The copper ions are bridged by two oxo atoms of the deprotonated ligands with a Cu-Cu distance of 3.042(4) Å. Each Cu(II) ion is in a distorted square-planar O2NBr environment. The compounds [Cu(N-oed)X]2 are diamagnetic and EPR-silent.
    01/2010; 112(5):309 - 313. DOI:10.1002/recl.19931120506
  • W. L. Driessen, W. L. Groeneveld
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    ABSTRACT: Five new complexes are reported with nitromethane as a ligand, viz. [M(CH3NO2)6]2+[FeCl4]2− where M is Mg(II), Mn(II), Fe(II), Co(II) and Ni(II). They are identified by chemical analysis and with the aid of physical measurements.The NO2 rocking mode (BI) shifts to higher frequencies; no shift in the NO stretching frequencies has been observed.In the far infrared a metal-dependent absorption band is observed, which is attributed to the metal-ligand stretching vibration.It is noticed that the relative size and stability of the anion influences such quantities as formation of the complex in the first place, shifts in ligand vibrational frequencies, ligand field transitions.
    01/2010; 88(5). DOI:10.1002/recl.19690880514
  • W. L. Driessen, F. Paap, J. Reedijk
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    ABSTRACT: The ligand 1,6-bis(3,5-dimethylpyrazol-1-yl)-2,5-dimethyl-2,5-diazahexane (debd), which has been synthesized from 3,5-dimethylpyrazole, N,N′-dimethylethanediamine and formaldehyde, partially disintegrates when reacted with zinc dichloride or with zinc dibromide in methanol. The resulting compounds contain the unique bis(pyrazolato)-bridged tetrahalogenido dizinc(II) anion. The compound [Zn(debd)Cl]2[Zn2(dmpz)2Cl4], with formula C42H70Cl6N16Zn4 and Mr = 1273.36, is obtained from methanol as monoclinic crystals, spacegroup P 21/c with a = 15.990(2) Å, b = 16.394(2) Å, c = 12.006(1) Å, β = 100.61(1)°, V = 3093.4(5) Å3, Zm = 2, Dx = 1.37 g.cm−3, as measured at room temperature with Mo(Kα) radiation to a final R value of 0.062 (wR = 0.065) for 2465 significant [I > 2σ-(I)] reflections.The asymmetric unit comprises half the formula unit. The cation consists of a Zn2+ ion in a distorted trigonal bipyramidal environment of a chloride ion at 2.221(3) Å, an amine nitrogen at 2.17(1) Å and a pyrazole nitrogen at 2.05(1) Å in the equatorial plane, with an amine nitrogen at 2.27(1) and a pyrazole nitrogen at 2.14(1) Å in the axial positions. The largest distortion is in the axis of the trigonal bipyramide with an N-Zn-N angle of 150.2(5)°.The anion consists of two Zn2+ ions, which are bridged by two deprotonated† dimethylpyrazole ligands with N-Zn distances of 1.97(1) and 1.98(1) Å, while each Zn2+ ion is further bound to two chloride ions at 2.276(4) and 2.261(4) Å. The Zn2+ ions are in an almost regular N2Cl2 tetrahedron.
    01/2010; 114(7). DOI:10.1002/recl.19951140704
  • W. L. Driessen, W. L. Groeneveld
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    ABSTRACT: A series of new complexes is reported with nitromethane as a ligand: viz. [M(CH3NO2)6]2+[SbCl6]2− where M is Mg(II), Ca(II), Sr(II), Mn(II), Fe(II), Co(II), Ni(II), and Zn(II).The compounds have been identified by chemical analysis and with the aid of physical measurements.No shift in the N → O stretching frequencies has been observed. The NO2 rocking mode (B1) shifts to higher frequencies.Ligand field spectra for the Co(II) and Ni(II) compounds are investigated. Values for Dq and B are reported and the ligand is placed in the spectrochemical and nephelauxetic series.It is concluded that complexes of nitromethane can serve as precursors of coordination compounds of other weakly nucleophilic ligands.
    01/2010; 88(4):491 - 498. DOI:10.1002/recl.19690880414
  • W.L. Driessen, W.L. Groeneveld
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    ABSTRACT: Twenty-three new coordination compounds are reported with butanone, acetophenone and chloroacetone as the ligands, viz. M(C2H5COCH3)6(InCl4)2, M(C6H5COCH3)6(InCl4)2, M(ClCH2COCH3)6(InCl4)2 and M(CICH2COCH3)6-(FeCl4)2 where M is Mg, Mn, Fe, Co, Ni, and Zn.In the complexes the carbonyl stretching vibration is shifted to lower frequencies with regard to this vibration in the free ligands, the magnitudes of the shifts are metal-dependent in the Irving-Williams order. Other ligand vibrations also shift on complexing.The presence of octahedral species M(O)62+ in the solid compounds was indicated by the ligand field spectra of the Fe(II), Co(II) and Ni(II) compounds. Values of Dq and B for the Co(II) and Ni(II) compounds are reported.
    01/2010; 90(3). DOI:10.1002/recl.19710900304
  • Willem L. Driessen
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    ABSTRACT: Procedures are described involving the condensation of l-(hydroxymethyl)pyrazole (1a) and l-(hydroxymethyl)-3,5-dimethylpyrazole (1b) with the following amines (products given in parentheses): ethylamine (2a and 2b), aniline (3a and 3b), N,N′-dimethyl- l,2-ethanediamine (4a and 4b), 1,2-ethanediamine (6a and 6b), diethylenetriamine (7a and 7b), triethylenetetramine (8a and 8b) and ammonia (9a and 9b). All amine hydrogens are completely substituted by pyrazol-1-ylmethyl groups (compounds 2a-9a) or (3,5-dimethylpyrazol-1-yl)methyl groups (compounds 2b-9b with yields being better than 90%.
    01/2010; 101(12):441 - 443. DOI:10.1002/recl.19821011204
  • J. Reedijk, W. L. Driessen, W. L. Groeneveld
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    ABSTRACT: Methods of calculation for the parameters Dq and B from the ligand-field spectra of octahedral cobalt(II) compounds are discussed. A method of calculation is introduced, which considers the lowering of the 4T1g (F) state by spin-orbit splitting. This calculation is applied to the spectra of 43 octahedrally coordinated cobalt(II) compounds.With the aid of the spectral data an energy-level diagram is constructed, into which the absorption bands are fitted.Comparison of calculated Dq and B values with corresponding values for isomorphous nickel(II) compounds shows that - in general - the crystalfield parameter Dq is highest for cobalt, although the differences with nickel are less than 4 % in most cases. The calculated B values corresponds with those of Ni, with differences less than 1 % for many ligands.
    01/2010; 88(9):1095 - 1109. DOI:10.1002/recl.19690880912
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    ABSTRACT: The synthesis and characterization of the copper tetrafluoroborate compound containing the bidentate N,S ligand 5-methyl-4-(ethylthiomethyl)imidazole (memi), [Cu(memi)2(BF4)2], is described. The activities of this compound and of [Cu(memi)2(H2O)2](NO3)2 as oxidation catalysts have been determined in the reaction of 2,6-dimethylphenol with molecular dioxygen to give polyphenylene oxide (PPO) and diphenoquinone (DPQ). For optimum catalysis, an additional base is required in order to dehydronate the phenol. Triethylamine proved to be most useful as a base. Initial reaction rates encountered are between 1 × 10−5 and 6 × 10−5M O2/s and ca. 50% of the phenol was converted after a reaction time of one hour. Less than 10% phenol was converted into DPQ. Both compounds have comparable reactivities.A single crystal of [Cu(memi)2(BF4)2] was used in an X-ray structure determination: monoclinic space group C2/c, a = 13.844(4) Å, b = 11.251(1) Å, c = 15.753(4) Å, β = 111.39 (2)°, Z = 4 and T = 293 K. The structure was solved using heavy-atom techniques and refined by least-squares methods to a residual R value of 0.050. The copper ion is in a centrosymmetric distorted octahedral environment with all chemically identical donor atoms in trans positions. The tetrafluoroborate anions are coordinated to the copper ion with relatively short distances, i.e. 2.55 Å; Cu-N and Cu-S distances are 1.93 and 2.41 Å.
    01/2010; 109(2):70 - 76. DOI:10.1002/recl.19901090208
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    ABSTRACT: Seven new complexes are reported with nitrobenzene as the ligand, viz. [M(C6H5NO2)6]2+[SbCl6]2− with M is Mg(II), Ca(II), Mn(II), Fe(II), Co(II), Ni(II), and Zn(II).No shift in the NO stretching frequencies has been observed. The NO2 out of plane bending vibration shifts to higher frequencies dependent on the metal ions.Investigation of ligand field spectra indicates the presence of octahedral species M(nitrobenzene)62+ in the solid compounds. Values for Dq and B for the Co and Ni compounds are reported.
    01/2010; 89(12):1271 - 1275. DOI:10.1002/recl.19700891207
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    ABSTRACT: The synthesis and characterization of transition-metal coordination compounds with the novel, tetradentate ligand 1,6-bis(5-methyl-4-imidazolyl)-2,5-dithiahexane (abbreviated bidhx) are described. The nitrates have the general formula M(bidhx)(NO3)2·nH2O (M = Co, Ni, Cu, Zn; n = 0 - 2). With the isothiocyanate anion, monomers M(bidhx)(NCS)2 containing Co, Ni and Zn and Cu(bidhx)(NCS)(NO3) as well as a dimer Cu2(bidhx)(NCS)3 were isolated. In all compounds, bidhx acts as a tetradentate ligand with both thioether sulfurs and both imidazole nitrogens coordinating. All compounds are six-coordinated in a distorted octahedral geometry, although, for the copper mixed-anion compound, a five-coordination in a square pyramidal geometry may also be possible. A single crystal of [Ni(NCS)2(bidhx)](MeOH) was used in a structure determination: monoclinic, space group C2/c, a = 13.0516(7) Å, b = 16.383(1) Å, c = 10.3758(9), Å, β = 101.095(6) deg, Z = 4 and T = 293 K. The structure was solved using heavy-atom techniques and refined by least-squares methods to an R value of 0.0508. The nickel ion is in a distorted octahedral environment with the two thiocyanates in a cis position. The nickel to nitrogen distances are ca. 2.04 Å; the nickel to sulfur distances are ca. 2.5 Å.
    01/2010; 107(3):163 - 166. DOI:10.1002/recl.19881070311
  • W.L. Driessen, W.L. Groeneveld
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    ABSTRACT: Twenty-two new coordination compounds are reported with acetaldehyde, propionaldehyde and benzaldehyde as the ligands, viz. M(CH3CHO)6(In-Cl4)2, M(CH3CHO)6(FeCl4)2, M(C2H5CHO)6(InCl4)2 and M(C6H5CHO)6(In-Cl4)2 with M is Mg, Mn, Fe, Co, Ni and (except for acetaldehyde) Zn.In the complexes the carbonyl stretching vibration is shifted to lower frequencies compared with this vibration in the free ligands. The magnitudes of the shifts are dependent on the metal ions. Frequency-shifts of other ligand vibrations are also observed. When the shifts are dependent on the metal ions the magnitudes of the shifts follow the Irving-Williams sequence.For the acetaldehyde and propionaldehyde solvates a metal-dependent absorption band appears in the far infrared, which is attributed to the metal-ligand stretching vibration. This band was not observed in the benzaldehyde solvates.Investigation of ligand field spectra indicated the presence of octahedral species M(O)62+ in the solid compounds. Values for Dq and B for the Co(II) and Ni(II) compounds are reported.A possible relationship between the groups attached to the CO group and the values obtained for the spectrochemical parameter Dq is described.
    01/2010; 90(1). DOI:10.1002/recl.19710900112
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    ABSTRACT: A series of azathia- and azaoxathiacrown ether macrocycles have been prepared in good yields via the use of N-boc-bis(2-chloroethyl)amine as a precursor, which minimises undesirable side reactions and facilitates subsequent deprotection to the free cyclic amine. The mono-aza macrocycles, [12]aneNS3, [12]aneNOS2, [15]aneNS4, [15]aneNO2S2 and [16]aneNS4 have been prepared via this route. The single-crystal X-ray structure of [12]aneNS3·HBr·2H2O confirms the macrocycle to be distorted quadrangular with the S-centres lying along the edges and six out of 12 torsion angles less than 90°. The synthesis of di-aza macrocycles utilising the diamide precursors, N,N′-bis(chloroacetyl)-1,2-diaminoethane and N,N′-bis(chloroacetyl)-1,3-diaminopropane, affords the free macrocycles [12]aneN2S2, [15]aneN2S3, [15]aneN2OS2, [16]aneN2S3 and [19]aneN2S4 after reduction of the intermediate cyclic amides. Reaction of 3,6-dioxa-1,8-octanediamine with the dimethyl ester of thiadiglycolic acid followed by reduction affords [15]aneN2O2S, while the hydroxy-substituted macrocycles [20]aneS6(OH)2, [13]aneS4(OH), and [26]aneS8(OH)2 have been prepared by reaction of 1,3-dichloro-2-hydroxypropane with the appropriate dithiol. The crystal structure of [20]aneS6(OH)2 shows two endo- and four exo-dentate S-centres as observed in the parent [18]aneS6. The N-aryl substituted macrocycles N-4-NO2Ph-[12]aneNS3 (N-4-nitrophenyl-7-aza-1,4,10-trithiacyclododecane) and N-4-NH2COPh-[12]aneNS3 (N-4-benzamido-7-aza-1,4,10-trithiacyclododecane) have been prepared by reaction of 4-substituted bis-tosylated N,N-bis(2-hydroxyethyl)aniline with 3-thia-1,5-pentanedithiol.
    Polyhedron 01/2006; 25(2):599-612. DOI:10.1016/j.poly.2005.11.006 · 2.05 Impact Factor
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    ABSTRACT: The Mannich condensation of formaldehyde with some amines and imidazoles rendered three bis-(amine–imidazole) ligands in a simple one pot reaction. Although these ligands are formally dinucleating, the copper(II) ions are held far apart, as shown by the Xray structures of five copper(II) compounds obtained with these ligands. Consequentially, these copper(II) compounds behave magnetically mononuclear.
    Inorganica Chimica Acta 04/2005; 358(7):2167-2173. DOI:10.1016/j.ica.2004.03.062 · 2.04 Impact Factor

Publication Stats

3k Citations
502.87 Total Impact Points

Institutions

  • 1984–2010
    • Leiden University
      • Section of Molecular Physics
      Leyden, South Holland, Netherlands
  • 1988–2002
    • University of Massachusetts Amherst
      • Department of Chemistry
      Amherst Center, Massachusetts, United States
  • 1997
    • University of Groningen
      Groningen, Groningen, Netherlands
  • 1996
    • AT&T Labs
      Austin, Texas, United States
  • 1985–1993
    • Utrecht University
      • Department of Chemistry
      Utrecht, Utrecht, Netherlands
    • Radboud University Nijmegen
      • Department of Chemistry
      Nymegen, Gelderland, Netherlands
  • 1990–1992
    • University of Strathclyde
      • Department of Pure and Applied Chemistry
      Glasgow, SCT, United Kingdom