Co-reporter:Lawrence W.-Y. Wong;Jack W.-H. Kan;Herman H.-Y. Sung
Acta Crystallographica Section C 2017 Volume 73(Issue 8) pp:625-631
Publication Date(Web):2017/08/01
DOI:10.1107/S2053229617009718
Spiroborate anions have potential for crystallization or resolution and chiral bis(mandelato)borate anions can be used for the efficient resolution of a diverse range of racemic cations via diastereomeric salt formation. The syntheses, X-ray crystal structures and solubilities of three chiral bis(mandelato)borate salts, namely poly[[aqua-μ3-bis[(R)-mandelato]borato-lithium(I)] monohydrate], [Li(C16H12BO6)(H2O)]n or Li[B(R-Man)2]·H2O, (1), ammonium bis[(R)-mandelato]borate, NH4+·C16H12BO6− or NH4[B(R-Man)2], (2), and tetra-n-butylammonium bis[(R)-mandelato]borate, C16H36N+·C16H12BO6− or NBu4[B(R-Man)2], (3), are reported. They all have a BS configuration and show a reasonably well-conserved anion geometry. The main conformational variation is the orientation of the two phenyl groups, supporting the idea that [B(Man)2]− is a semi-rigid anion. The salts are differentially soluble in a range of solvents, meaning they could be useful as reagents for resolution via a metathesis crystallization approach.
Co-reporter:Yat-Ming So, Yang Li, Ka-Chun Au-Yeung, Guo-Cang Wang, Kang-Long Wong, Herman H. Y. Sung, Polly L. Arnold, Ian D. Williams, Zhenyang Lin, and Wa-Hung Leung
Inorganic Chemistry 2016 Volume 55(Issue 20) pp:10003-10012
Publication Date(Web):May 19, 2016
DOI:10.1021/acs.inorgchem.6b00480
The reactivity of the cerium(IV) oxo complex [(LOEt)2CeIV(═O)(H2O)]·MeC(O)NH2 (1; LOEt– = [CoCp{P(O)(OEt)2}3]−, where Cp = η5-C5H5) toward electrophiles and Brønsted acids has been investigated. The treatment of 1 with acetic anhydride afforded the diacetate complex [CeIV(LOEt)2(O2CMe)2] (2). The reaction of 1 with B(C6F5)3 yielded [CeIV(LOEt)2(Me2CONH2)2][B(C6F5)3(OH)]2 (3), in which the [B(C6F5)3(OH)]− anions are H-bonded to the O-bound acetamide ligands. The treatment of 1 with HCl and HNO3 afforded [CeIV(LOEt)2Cl2] and [CeIV(LOEt)2(NO3)2], respectively. Protonation of 1 with triflic acid (HOTf) gave the diaqua complex [CeIV(LOEt)2(H2O)2](OTf)2 (4), in which the triflate anions are H-bonded to the two aqua ligands. The treatment of 1 with phenol afforded the phenoxide complex [CeIV(LOEt)2(OPh)2] (5). The oxo-bridged bimetallic complex [(LOEt)2(Me2CONH2)CeIV(O)NaLOEt] (6) with the Ce–Ooxo and Na–Ooxo distances of 1.953(4) and 2.341(4) Å, respectively, was obtained from the reaction of 1 with [NaLOEt]. Density functional theory calculations showed that the model complex [(LOMe)2CeIV(Me2CONH2)(O)NaLOMe] (6A; LOMe– = [CoCp{P(O)(OMe)2}3]−) contains a polarized Ce═O multiple bond. The energy for dissociation of the {NaLOMe} fragment from 6A in acetonitrile was calculated to be +33.7 kcal/mol, which is higher than that for dissociation of the H-bonded acetamide from [(LOMe)2CeIV(═O)(H2O)]·MeC(O)NH2 (1A) (calculated to be +17.4 kcal/mol). In hexanes containing trace water, complex 1 decomposed readily to a mixture of a tetranuclear cerium(IV) oxo cluster, [CeIV4(LOEt)4(μ4-O)(μ2-O)4(μ2-OH)2] (7), and a cerium(III) complex, [CeIII(LOEt)2(H2O)2][LOEt] [8(LOEt)], whereas the cerium/sodium oxo complex 6 is stable under the same conditions. The crystal structures of 3, 4·H2O, 6, and 8(LOEt) have been determined.
Co-reporter:Kang-Long Wong, Yat-Ming So, Guo-Cang Wang, Herman H.-Y. Sung, Ian D. Williams and Wa-Hung Leung
Dalton Transactions 2016 vol. 45(Issue 21) pp:8770-8776
Publication Date(Web):26 Apr 2016
DOI:10.1039/C6DT00678G
Heterometallic CeIV/M (M = MoVI, ReVII, VV) oxo clusters supported by the Kläui tripodal oxygen ligand [(η5-C5H5)Co{P(O)(OEt)2}3]− (LOEt−) have been synthesized and structurally characterized, and the catalytic activity of the CeIV/VV oxo cluster in the oxidation of thioanisoles has been studied. Treatment of [Ce(LOEt)Cl3] (1) with [Ag2MoO4] afforded the reported CeIV/MoVI cluster [H4(CeLOEt)6Mo9O38] (2), whereas that with [AgReO4] yielded the CeIV/ReVII cluster [{LOEtCe(ReO4)2(H2O)(μ-ReO4)}2] (3) that contains an 8-membered Ce2Re2O4 ring. Treatment of 1 with [Ag3VO4] afforded the CeIV/VV cluster [H2(CeLOEt)4(VO)4(μ4-O)(μ3-O)12] (4) containing a {Ce4V4O13} oxo-metallic core. The solid-state structure of 4 consists of four {VO4}3− units bridged by four {LOEtCe3+} moieties and a μ4-oxo ligand. Each Ce atom in 4 is 9-coordinated, whereas the geometry around each V atom is pseudo square pyramidal with a terminal oxo at the apical position. Cluster 4 is an active catalyst for the oxidation of substituted thioanisoles with tert-butyl hydroperoxide. For example, the oxidation of thioanisole with tert-butyl hydroperoxide in the presence of 0.01 mol% of 4 gave a ca. 30:1 mixture of the sulfoxide and sulfone products in 96% yield.
Co-reporter:Wei Bai, Ka-Ho Lee, Herman H. Y. Sung, Ian D. Williams, Zhenyang Lin, and Guochen Jia
Organometallics 2016 Volume 35(Issue 22) pp:3808-3815
Publication Date(Web):November 15, 2016
DOI:10.1021/acs.organomet.6b00653
Although alkyne metathesis reactions mediated by high-valent d0 carbyne complexes are well established, similar reactions mediated by well-defined low-valent (non-d0) carbyne complexes are rare. This work demonstrates that d2 Re(V) carbyne complexes Re(≡CR)Cl2(PMe2Ph)3 (R = CH2(o-C6H4Br), Ph, CO2Et) can undergo stoichiometric alkyne metathesis reactions. For example, reactions of Re{≡CCH2(o-C6H4Br)}Cl2(PMe2Ph)3 with TMSC≡CR (R = CO2Et, CH2Ph) and PhC≡CPh produced carbyne complexes Re(≡CR)Cl2(PMe2Ph)3 and Re(≡CPh)Cl2(PMe2Ph)3, respectively. Theoretical studies suggest that the metathesis reactions most likely proceed through six-coordinate alkyne-carbyne intermediates Re(≡CR)Cl2(η2-alkyne)(PMe2Ph)2 that undergo reversible cycloaddition reactions.
Co-reporter:Dr. Jiangxi Chen;Dr. Ka-Ho Lee;Dr. Herman H. Y. Sung;Dr. Ian D. Williams;Dr. Zhenyang Lin;Dr. Guochen Jia
Angewandte Chemie 2016 Volume 128( Issue 25) pp:7310-7314
Publication Date(Web):
DOI:10.1002/ange.201601562
Abstract
The 12-membered-ring metallacycles [mer-Re{≡CCH=C(R)C≡C−}Cl(PMe2Ph)3)]2 (R=CMe3, 1-adamantyl), which are organometallic analogues of antiaromatic octadehydro[12]annulene, are prepared by heating the methyl carbyne complexes mer-Re{≡CCH=C(R)C≡CH}(CH3)Cl(PMe2Ph)3. An intermolecular σ-bond metathesis between the Re−CH3 bond and the acetylenic C−H bond is proposed for their formation.
Co-reporter:Dr. Jiangxi Chen;Dr. Ka-Ho Lee;Dr. Herman H. Y. Sung;Dr. Ian D. Williams;Dr. Zhenyang Lin;Dr. Guochen Jia
Angewandte Chemie International Edition 2016 Volume 55( Issue 25) pp:7194-7198
Publication Date(Web):
DOI:10.1002/anie.201601562
Abstract
The 12-membered-ring metallacycles [mer-Re{≡CCH=C(R)C≡C−}Cl(PMe2Ph)3)]2 (R=CMe3, 1-adamantyl), which are organometallic analogues of antiaromatic octadehydro[12]annulene, are prepared by heating the methyl carbyne complexes mer-Re{≡CCH=C(R)C≡CH}(CH3)Cl(PMe2Ph)3. An intermolecular σ-bond metathesis between the Re−CH3 bond and the acetylenic C−H bond is proposed for their formation.
Co-reporter:Lawrence W-Y. Wong, Jack W-H. Kan, Thanh-ha Nguyen, Herman H-Y. Sung, Dang Li, Alex S-F. Au-Yeung, Rajpal Sharma, Zhenyang Lin and Ian D. Williams
Chemical Communications 2015 vol. 51(Issue 87) pp:15760-15763
Publication Date(Web):02 Sep 2015
DOI:10.1039/C5CC04977F
Bis(mandelato)borate [B(Man)2]− (R- or S-) anions are simply prepared and appear widely effective for resolution of racemic cations. Three examples demonstrate their scope; the alkaloid tetrahydropalmatine (THP), 1,2-diaminopropane (1,2-dap) and the metal–organic complex [Co(phen)3]3+ are readily resolved, either by a facile one-pot procedure, or via counter-ion metathesis.
Co-reporter:Jiangxi Chen, Ka-Ho Lee, Tingbin Wen, Feng Gao, Herman H. Y. Sung, Ian D. Williams, Zhenyang Lin, and Guochen Jia
Organometallics 2015 Volume 34(Issue 5) pp:890-896
Publication Date(Web):February 27, 2015
DOI:10.1021/om501181u
Treatment of the osmabenzyne complex Os{≡C-C(SiMe3)═C(CH3)-C(SiMe3)═CH−}Cl2(PPh3)2 with Mo(CO)6 in refluxing benzene produced the η5-chlorocyclopentadienyl complex Os{η5-C5HCl(CH3)(SiMe3)2}Cl(CO)(PPh3) and Mo(CO)5(PPh3). A computational study suggests that the chlorocyclopentadienyl complex is most likely produced via the carbene intermediate Os{═C(C(SiMe3)═C(CH3)-C(SiMe3)═CH−)}Cl2(CO)(PPh3) formed by a migratory insertion reaction of the osmabenzyne complex Os{≡C-C(SiMe3)═C(CH3)-C(SiMe3)═CH}Cl2(CO)(PPh3). DFT calculations show that the relative thermal stability of metallabenzynes Os(≡C-CH═CHCH═CH)Cl2(L)2 and the corresponding isomeric carbene complexes Os{═C(−CH═CHCH═CH−)}Cl2(L)2 as well as the chlorocyclopentadienyl complexes Os(η5-C5ClH4)Cl(L)2 (L = CO, phosphine, pyridine, amine) is strongly dependent on ligand L.
Co-reporter:Dr. Guo-Cang Wang;Dr. Yat-Ming So;Kang-Long Wong;Ka-Chun Au-Yeung;Dr. Herman H.-Y. Sung; Ian D. Williams; Wa-Hung Leung
Chemistry - A European Journal 2015 Volume 21( Issue 45) pp:16126-16135
Publication Date(Web):
DOI:10.1002/chem.201502173
Abstract
A tetranuclear CeIV oxo cluster compound containing the Kläui tripodal ligand [Co(η5-C5H5){P(O)(OEt)2}3]− (LOEt−) has been synthesized and its reactions with H2O2, CO2, NO, and Brønsted acids have been studied. The treatment of [Ce(LOEt)(NO3)3] with Et4NOH in acetonitrile afforded the tetranuclear CeIV oxo cluster [Ce4(LOEt)4O7H2] (1) containing an adamantane-like {Ce4(μ2-O)6} core with a μ4-oxo ligand at the center. The reaction of 1 with H2O2 resulted in the formation of the peroxo cluster [Ce4(LOEt)4(μ4-O)(μ2-O2)4(μ2-OH)2] (2). The treatment of 1 with CO2 and NO led to isolation of [Ce(LOEt)2(CO3)] and [Ce(LOEt)(NO3)3], respectively. The protonation of 1 with HCl, ROH (R=2,4,6-trichlorophenyl), and Ph3SiOH yielded [Ce(LOEt)Cl3] (3), [Ce(LOEt)(OR)3] (4), and [Ce(LOEt)(OSiPh3)3] (5), respectively. The chloride ligands in 3 are labile and can be abstracted by silver(I) salts. The treatment of 3 with AgOTs (OTs−=tosylate) and Ag2O afforded [Ce(LOEt)(OTs)3] (6) and 1, respectively. The electrochemistry of the Ce-LOEt complexes has been studied by using cyclic voltammetry. The crystal structures of complexes 1–5 have been determined.
Co-reporter:Yat-Ming So;Dr. Guo-Cang Wang;Dr. Yang Li;Dr. Herman H.-Y. Sung;Dr. Ian D. Williams;Dr. Zhenyang Lin;Dr. Wa-Hung Leung
Angewandte Chemie 2014 Volume 126( Issue 6) pp:1652-1655
Publication Date(Web):
DOI:10.1002/ange.201309764
Abstract
Whereas terminal oxo complexes of transition and actinide elements are well documented, analogous lanthanide complexes have not been reported to date. Herein, we report the synthesis and structure of a cerium(IV) oxo complex, [CeO(LOEt)2(H2O)]⋅MeC(O)NH2 (1; LOEt−=[Co(η5-C5H5){P(O)(OEt)2}3]−), featuring a short CeO bond (1.857(3) Å). DFT calculations indicate that the hydrogen bond to cocrystallized acetamide plays a key role in stabilizing the CeO moiety of 1 in the solid state. Complex 1 exhibits oxidizing and nucleophilic reactivity.
Co-reporter:Wei Bai;Sunny Kai San Tse;Ka Ho Lee;Herman Ho-Yung Sung
Science China Chemistry 2014 Volume 57( Issue 8) pp:1079-1089
Publication Date(Web):2014 August
DOI:10.1007/s11426-014-5143-6
Treatment of RuCl2(PPh3)3 with 6-dimethylaminopentafulvene in THF in the presence of water produced (η5-C5H4CHO) RuCl(PPh3)2, which was reduced by NaBH4 to give the Ru-H⋯HO dihydrogen bonded complex (η5-C5H4CH2OH) RuH(PPh3)2. The dihydrogen bonded complex (η5-C5H4CH2OH)RuH(PPh3)2 could also be synthesized by the reduction of complex (η5-C5H4CHO)RuH(PPh3)2, which was obtained by the reaction of RuHCl(PPh3)3 with 6-dimethylaminopentafulvene in the presence of water. The analogous dihydrogen bonded osmium complex (η5-C5H4CH2OH)OsH(PPh3)2 was similarly prepared. Single crystal structures and DFT calculations support the presence of intra-molecular H…H interaction, with separations of around 1.9 to 2.0 Å.
Co-reporter:Yat-Ming So;Dr. Guo-Cang Wang;Dr. Yang Li;Dr. Herman H.-Y. Sung;Dr. Ian D. Williams;Dr. Zhenyang Lin;Dr. Wa-Hung Leung
Angewandte Chemie International Edition 2014 Volume 53( Issue 6) pp:1626-1629
Publication Date(Web):
DOI:10.1002/anie.201309764
Abstract
Whereas terminal oxo complexes of transition and actinide elements are well documented, analogous lanthanide complexes have not been reported to date. Herein, we report the synthesis and structure of a cerium(IV) oxo complex, [CeO(LOEt)2(H2O)]⋅MeC(O)NH2 (1; LOEt−=[Co(η5-C5H5){P(O)(OEt)2}3]−), featuring a short CeO bond (1.857(3) Å). DFT calculations indicate that the hydrogen bond to cocrystallized acetamide plays a key role in stabilizing the CeO moiety of 1 in the solid state. Complex 1 exhibits oxidizing and nucleophilic reactivity.
Co-reporter:Chun-Lung Choi, Yu-Fong Yen, Herman H.-Y. Sung, Alvin W.-H. Siu, Samadara Thushari Jayarathne, Kam Sing Wong and Ian D. Williams
Journal of Materials Chemistry A 2011 vol. 21(Issue 24) pp:8547-8549
Publication Date(Web):11 May 2011
DOI:10.1039/C1JM11102G
Remarkable enhancement and quenching of photo-luminescent emissions have been found in various mixed-lanthanide carboxylate polymers. In (Eu0.1:Tb99.9)2(2,2-biphenate)3(H2O)2 the Eu emission is comparable to the Eu homo-polymer, whilst the original Tb emission is reduced by ca. 80%. Either sensitized energy transfer or the reduction of self-quenching through dilution may play a dominant role.
Co-reporter:Samadara Thushari, John A. K. Cha, Herman H.-Y. Sung, Stephen S.-Y. Chui, Andy L.-F. Leung, Yu-Fong Yen and Ian D. Williams
Chemical Communications 2005 (Issue 44) pp:5515-5517
Publication Date(Web):12 Oct 2005
DOI:10.1039/B508574H
L-Tartrate ions can endure hydrothermal conditions up to 160 °C to form the robust, enantiopure open-framework coordination polymers [Ln2(L-TAR)3(H2O)2]3H2O, 1; the addition of succinate results in formation of the related [Ln2(L-TAR)2(SUC)(H2O)2]5.5H2O, 2 with larger channels than 1, whereas racemic D/L-tartrate gives the more condensed [Ln2(D/L-TAR)3(H2O)2], 3. TAR = [C4H4O6]2−.
Co-reporter:Candy Z-J. Lin, Stephen S-Y. Chui, Samuel M-F. Lo, Fanny L-Y. Shek, Mingmei Wu, Kinga Suwinska, Janusz Lipkowski and Ian D. Williams
Chemical Communications 2002 (Issue 15) pp:1642-1643
Publication Date(Web):02 Jul 2002
DOI:10.1039/B201501N
Two microporous copper isonicotinate polymers [Cu(OH)(INA)] and [Cu(INA)2] have been formed hydrothermally in good yield and purity; each have 1D channels of ca. 4 × 6 Å dimension, but with quite different hydrophilicities; both frameworks retain structural integrity to above 200 °C, however whilst [Cu(OH)(INA)] is also chemically stable, [Cu(INA)2] is highly labile and readily transforms to the molecular complex [Cu(INA)2(H2O)4] in water at room temperature.
Co-reporter:Ian D. Williams, Teresa S.-C. Law, Herman H-Y. Sung, Ge-Hui Wen, Xi-Xiang Zhang
Solid State Sciences 1998 Volume 2(Issue 1) pp:47-55
Publication Date(Web):January 1998
DOI:10.1016/S1293-2558(00)00114-X
Synthesis of [enH2][Mn3(V2O7)2(H2O)2] 1, the first of a new class of organically derivatized mixed metal oxides, is achieved at pH 8 and 140°C by hydrothermal reaction of [Mn3O(OAc)6(py)3][BF4], V2O5, NH2CH2CH2NH2 (en) and H3BO3 in a 0.67: 1: 6: 10 ratio. Crystals of 1 are triclinic P-1, a=5.743(1) Å, b=7.931(1) Å, c=9.313(1) Å, α=68.54(1), β=85.78(1), γ=84.50(1)°, V=392.62(9) Å3. The X-ray structure refined to R=0.025. Compound 1 has an anionic open 3-D framework based on linear tri-manganese units of edge shared [Mn(II)O6] octahedra connected through divanadate [V2O7] groups. The organic counterions are located in 1-D tunnels generated from six-membered [Mn2V4] rings. The temperature dependent magnetic susceptibility of 1 indicates a paramagnetic to anti-ferromagnetic transition with a Néel temperature of 10 K.
Co-reporter:Kang-Long Wong, Yat-Ming So, Guo-Cang Wang, Herman H.-Y. Sung, Ian D. Williams and Wa-Hung Leung
Dalton Transactions 2016 - vol. 45(Issue 21) pp:NaN8776-8776
Publication Date(Web):2016/04/26
DOI:10.1039/C6DT00678G
Heterometallic CeIV/M (M = MoVI, ReVII, VV) oxo clusters supported by the Kläui tripodal oxygen ligand [(η5-C5H5)Co{P(O)(OEt)2}3]− (LOEt−) have been synthesized and structurally characterized, and the catalytic activity of the CeIV/VV oxo cluster in the oxidation of thioanisoles has been studied. Treatment of [Ce(LOEt)Cl3] (1) with [Ag2MoO4] afforded the reported CeIV/MoVI cluster [H4(CeLOEt)6Mo9O38] (2), whereas that with [AgReO4] yielded the CeIV/ReVII cluster [{LOEtCe(ReO4)2(H2O)(μ-ReO4)}2] (3) that contains an 8-membered Ce2Re2O4 ring. Treatment of 1 with [Ag3VO4] afforded the CeIV/VV cluster [H2(CeLOEt)4(VO)4(μ4-O)(μ3-O)12] (4) containing a {Ce4V4O13} oxo-metallic core. The solid-state structure of 4 consists of four {VO4}3− units bridged by four {LOEtCe3+} moieties and a μ4-oxo ligand. Each Ce atom in 4 is 9-coordinated, whereas the geometry around each V atom is pseudo square pyramidal with a terminal oxo at the apical position. Cluster 4 is an active catalyst for the oxidation of substituted thioanisoles with tert-butyl hydroperoxide. For example, the oxidation of thioanisole with tert-butyl hydroperoxide in the presence of 0.01 mol% of 4 gave a ca. 30:1 mixture of the sulfoxide and sulfone products in 96% yield.
Co-reporter:Mingmei Wu, Teresa S-C. Law, Herman H-Y. Sung, Jiwen Cai and Ian D. Williams
Chemical Communications 2005(Issue 14) pp:NaN1829-1829
Publication Date(Web):2005/02/09
DOI:10.1039/B414697B
The hydrothermal synthesis of three new vanadoborate compounds with elliptical (V10B28O74H8) clusters is described. The clusters contain pairs of bimetallic Zn2 or Mn2 units.
Co-reporter:Chun-Lung Choi, Yu-Fong Yen, Herman H.-Y. Sung, Alvin W.-H. Siu, Samadara Thushari Jayarathne, Kam Sing Wong and Ian D. Williams
Journal of Materials Chemistry A 2011 - vol. 21(Issue 24) pp:NaN8549-8549
Publication Date(Web):2011/05/11
DOI:10.1039/C1JM11102G
Remarkable enhancement and quenching of photo-luminescent emissions have been found in various mixed-lanthanide carboxylate polymers. In (Eu0.1:Tb99.9)2(2,2-biphenate)3(H2O)2 the Eu emission is comparable to the Eu homo-polymer, whilst the original Tb emission is reduced by ca. 80%. Either sensitized energy transfer or the reduction of self-quenching through dilution may play a dominant role.
Co-reporter:Lawrence W-Y. Wong, Jack W-H. Kan, Thanh-ha Nguyen, Herman H-Y. Sung, Dang Li, Alex S-F. Au-Yeung, Rajpal Sharma, Zhenyang Lin and Ian D. Williams
Chemical Communications 2015 - vol. 51(Issue 87) pp:NaN15763-15763
Publication Date(Web):2015/09/02
DOI:10.1039/C5CC04977F
Bis(mandelato)borate [B(Man)2]− (R- or S-) anions are simply prepared and appear widely effective for resolution of racemic cations. Three examples demonstrate their scope; the alkaloid tetrahydropalmatine (THP), 1,2-diaminopropane (1,2-dap) and the metal–organic complex [Co(phen)3]3+ are readily resolved, either by a facile one-pot procedure, or via counter-ion metathesis.
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