Oxorhenium(V) complexes with 1H-benzimidazole-2-carboxylic acid - Synthesis, structural characterization and catalytic application in epoxidation reactions

被引：12

作者：

Machura, B. ^{[1
]}

Wolff, M. ^{[1
]}

Benoist, E. ^{[2
,3
]}

Schachner, J. A. ^{[4
]}

Moesch-Zanetti, N. C. ^{[4
]}

Takao, K. ^{[5
]}

Ikeda, Y. ^{[5
]}

机构：

[1] Univ Silesia, Inst Chem, Dept Crystallog, PL-40006 Katowice, Poland

[2] CNRS, Lab Synth & Physicochim Mol Interet Biol, SPCMIB, UMR 5068, F-31062 Toulouse 9, France

[3] Univ Toulouse, Lab Synth & Physicochim Mol Interet Biol, SPCMIB, UPS,UMR 5068, F-31062 Toulouse 9, France

[4] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

[5] Tokyo Inst Technol, Nucl Reactors Res Lab, Meguro Ku, Tokyo 1528550, Japan

来源：

POLYHEDRON | 2014年 / 69卷

关键词：

Oxorhenium(V) complexes; Multidentate heterocyclic aromatic; carboxylic acid; X-ray crystal structure; Epoxidation; CARBOXYLIC-ACIDS; OXO-COMPLEXES; BASIS-SET; POTENTIALS;

D O I：

10.1016/j.poly.2013.12.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Depending on the experimental conditions three novel oxorhenium(V) complexes incorporating 1H-benzimidazole-2-carboxylic acid (2-bimH) cis-Cl,Cl-[ReOCl2(2-bim)(PPh3)] (1), cis-Br,Br-[ReOBr2 (2-bim)(PPh3)] (2) and [ReOCl(2-bim)(2)] (3) were synthesized. The reported complexes were characterized by spectroscopic methods (IR, H-1, C-13, P-31 NMR, UV-Vis, ESI+-MS), cyclic voltammetry and single crystal X-ray diffraction analysis. To elucidate the structural, spectroscopic and bonding properties, calculations at the DFT level were undertaken. The catalytic competencies of compounds 1-3 were investigated in the epoxidation of cyclooctene with tert-butyl hydroperoxide (TBHP) as oxidant. The studies revealed higher catalytic activities for complexes based on one 1H-benzimidazole-2-carboxylic acid (compounds 1 and 2) and phosphine as ancillary ligand, with the yield of cyclooctane-oxide varying between 60% and 64% (50 degrees C, 24 h). (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：205 / 218

页数：14

共 44 条

[31] Mizuguchi K., 1998, J ALLOY COMPD, V271-273, P163
[32] Nakamoto K., 1986, INFRARED RAMAN SPECT
[33] Bis(1H-benzimidazole-2-carboxylato-k(2)N(3),O) bis(ethanol-kO) manganese(II)
Nie, Jian-Hua
Lin, Yue-Hua
Xu, Chun-Tao
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : M1288 - +
[34] PRODUCTS FROM REACTION OF TRANS-OXOTRIHALOGENOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) WITH CARBOXYLIC ACIDS AND RELATED COMPOUNDS
ROUSCHIA.G
WILKINSO.G
[J]. JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1966, (05): : 465 - &
[35] Oxorhenium(V) Complexes with Ketiminato Ligands: Coordination Chemistry and Epoxidation of Cyclooctene
Schroeckeneder, Albert
Traar, Pedro
Raber, Georg
Baumgartner, Judith
Belaj, Ferdinand
Mosch-Zanetti, Nadia C.
[J]. INORGANIC CHEMISTRY, 2009, 48 (24) : 11608 - 11614
[36] Sheldrick GM, 2015, ACTA CRYSTALLOGR C, V71, P3, DOI [10.1107/S2053229614024218, 10.1107/S2053273314026370, 10.1107/S0108767307043930]
[37] Rhenium(V)-catalyzed synthesis of 2-deoxy-α-glycosides
Sherry, BD
Loy, RN
Toste, FD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) : 4510 - 4511
[38] Oxidorhenium(V) Complexes with Oxazolinylmethoxido Ligands - Structure and Catalytic Epoxidation
Terfassa, Belina
Traar, Pedro
Volpe, Manuel
Moesch-Zanetti, Nadia C.
Raju, V. J. T.
Megersa, Negussie
Retta, Negussie
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (28) : 4434 - 4440
[39] Oxorhenium(V) Complexes with Pyrazole Based Aryloxide Ligands and Application in Olefin Epoxidation
Traar, Pedro
Schachner, Joerg A.
Steiner, Lisa
Sachse, Anna
Volpe, Manuel
Moesch-Zanetti, Nadia C.
[J]. INORGANIC CHEMISTRY, 2011, 50 (05) : 1983 - 1990
[40] Weinhold F., 2005, Valency and Bonding: A Natural Bond Orbital DonorAcceptor Perspective

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