Diels-Alder reaction with cyclopentadiene and electronic structures of (η5-cyclopentadienyl)M(CO)x(η1-N-maleimidato) (M = Fe, Mo, W, x=2 or 3)

被引:6
作者
Rudolf, Bogna [1 ]
Palusiak, Marcin [2 ]
Zakrzewski, Janusz [1 ]
机构
[1] Univ Lodz, Dept Organ Chem, PL-90136 Lodz, Poland
[2] Univ Lodz, Dept Crystallog & Crystal Chem, PL-90236 Lodz, Poland
关键词
Maleimidato complexes; Cyclopentadiene; Diels-Alder reaction; X-ray structure; DFT calculations; EFFECTIVE CORE POTENTIALS; MOLECULAR CALCULATIONS; CRYSTAL-STRUCTURE; COMPLEXES; PROTEIN; BIOMOLECULES; ATOMS;
D O I
10.1016/j.jorganchem.2008.12.031
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diels-Alder reaction of (eta(5)-cyclopentadienyl)M(CO)(x)(eta(1)-N-maleimidato) complexes (M = Fe, Mo, W, x = 2 or 3) with cyclopentadiene has been studied. The observed order of reactivity was: N-ethylmaleimide > W complex > Mo complex > Fe complex. The X-ray structures of the adducts have been determined for M = W and Fe. DFT calculations on the starting complexes have been performed to explain the observed reactivity order. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:1354 / 1358
页数:5
相关论文
共 30 条
[1]  
[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]  
Berkin A, 2002, CHEM-EUR J, V8, P4424, DOI 10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO
[4]  
2-1
[5]   Diels-Alder ligation and surface immobilization of proteins [J].
de Araújo, AD ;
Palomo, JM ;
Cramer, J ;
Köhn, M ;
Schröder, H ;
Wacker, R ;
Niemeyer, C ;
Alexandrov, K ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (02) :296-301
[6]   Diels-Alder ligation of peptides and proteins [J].
de Araujo, Aline Dantas ;
Palomo, Jose M. ;
Cramer, Janina ;
Seitz, Oliver ;
Alexandrov, Kirill ;
Waldmann, Herbert .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :6095-6109
[7]   ABSORPTION CORRECTION IN CRYSTAL STRUCTURE ANALYSIS [J].
DEMEULENAER, J ;
TOMPA, H .
ACTA CRYSTALLOGRAPHICA, 1965, 19 :1014-+
[8]   Solvent effects on the 9-hydroxymethylanthracene plus N-ethylmaleimide Diels-Alder reaction.: A theoretical study [J].
García, JI ;
Mayoral, JA ;
Salvatella, L .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1456-1458
[9]   Cysteine-specific, covalent anchoring of transition organometallic complexes to the protein papain from Carica papaya [J].
Haquette, Pierre ;
Salmain, Michele ;
Svedlung, Karolina ;
Martel, Annie ;
Rudolf, Bogna ;
Zakrzewski, Janusz ;
Cordier, Stephane ;
Roisnel, Thierry ;
Fosse, Celine ;
Jaouen, Gerard .
CHEMBIOCHEM, 2007, 8 (02) :224-231
[10]  
HAY PJ, 1985, J CHEM PHYS, V82, P299, DOI [10.1063/1.448799, 10.1063/1.448800]