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231,Àt METAL CARBONYL FLUORIDE COMPLEXES by Ernst Horn,B. Sc. (Hons, ) A Thesis presented for the degree of Doctor of Philosophy Department of Physical and Inorganic Chenistry The University of Adelaide August 1983 To My Mother and In Mernory of My Father TABLE OF CONTENTS Page STJMMARY vi STATEIvIENT ix ACKNOWLEDGEMENTS x ABBREVIATIONS xi CHAPTER 1 . INTRODUCTION 1 1.1 Manganese and Rhenium Carbonyl Fluorides 2 1 .1.1 t"tanganese Fluorides 2 L.1.2 Rheníun Fluorides 4 t.2 Coordinated Fluoro- and Oxy-ligands 5 1.3 Characterization of Metal Carbonyls 7 CFIAPTER 2 . METAL CARBONYL CLUSTERS 11 2.t Introduction 11 'r) Preparation and Properties of the Clusters L2 L2 2.2.L tllftr(CO) s{px(OH) r-x}l r+ and IRe(C0) sF] b'4(Hz0) L4 2.2.2 [M(Co) 3F] 4 15 2.2.s [Rh(PPha)X] + 2.3 Structure Determination of lI'fri(CO) g{Fx, (OH)r-x}] +'2(CeHs) L7 2.3.L Crystal Data L7 2.3.2 Structure Solution and Refinement 18 2.3.3 Description of the Structure 19 2.3.4 Discussion 25 2.4 Structure Dete¡mination of [Re(CO) gF],*'4(HzO) 26 2.4.t Crystal Data 26 2.4.2 Structure Solution and Refinement 27 2.4.3 Description of the Structure 33 aÉ Structure Deternination of [Rh(PPh3)C1] q 34 2.5.L Crystal Data 34 2.5.2 Structure Solution and Refinement 34 2.5.3 Description of the Structure 40 11 Page 2.6 Discussion 42 2.7 Experinental 47 CHAPTER 3 - COORDINATED FLUORIDE IN RFIENIUM(I) COMPLEXES 50 3.1 Introduction 50 3.2 Preparation and Properties of [Re(C0) s (Lz)F] zH'HOBFg 52 3.2.L Preparation s2 3.2.2 Properties 52 3.3 Preparation and Properties of [Re(C0)s(Lz)F] 54 3.3.L Preparation s4 3.3.2 Properties 54 3.4 Structure Determination of [Re(C0) 3 (tnen)F]H'HOBFg 57 3.4.7 Crystal Data s7 3.4.2 Structural Solution and Refinement 57 3.4.3 Description of the Structure 59 3.5 Structure Determination of [Re(C0) 3 (tmen)F] 66 3.5.1 Crystal Data 66 3.5.2 Structural Solution and Refinement 67 3.5.3 Description of the Structure 72 5.6 Discussion t5 3. 7 Experimental 77 CHAPTER 4 . MANGANESE CARBONYL COMPLEXES 81 4.1 Introduction 81 4.2 Preparations 83 4.2.7 ll\frl(c0) sielonfrla]20C1031 83 . 4 .2 .2 tltr (co) s (diphos) (BF 30H) I å (dpeo) 83 4.2.3 Preparation of fac-Irtut(CO) s (Lz)F 85 4.3 Structure Deternination of [I,ln(C0) a{n¡Oetr¡ r}rOCtOg] 87 4.3.I Crystal Data 87 4.3.2 Structure Solution and Refinement 89 4.3.3 Description of the Structure 89 111 Page . 4.4 Structure Determination of [{n(C0) 3 (diphos) (BF30H) ] I (dpeo) 94 4.4.t Crystal Data 94 4.4.2 Stnrcture Solution and Refinement 96 4.4.3 Description of the Structure 97 4.5 Discussion 104 4.5.1 Metal Carbonyl Perchlorates t04 4.5.2 Metal Carbonyl Trifluorohydroxy borates 106 4.5.3 Manganese Carbonyl Fluorides 108 4.6 Experinental 109 cHAprER 5 - METAL CARBoNYL AQUA CoMPLEXES It2 5.1 Introduction tt2 s.2 Preparations and Properties 113 *.y- s.2.1 [M(co) g (Lz) (Hzo) ] tt3 5.2.2 Re(C0) s (Lz)Y.HzO It4 5.2.3 Characterization by Infrared Spectroscopy 115 5.2.4 Reactions of [M(CO) s (Lz) (HzO)]+.Y- and L2T Re (C0) s (Lz)Y. (HzO) 5.3 Structure Determination of [Re(CO) s (HzO) 1*.AsFf L22 5.3. 1 Crystal Data r22 s.3.2 Structure Solution and Refinement 728 5.3.3 Description of the Structure L28 5.4 Structure Determination of [Re(CO) 3 (tmen) (HzO) 1*.Asff 131 5.4.1 Crystal Data 73L 5.4.2 Structure Solution and Refinement r33 5.4.3 Description of the Structure 138 5.5 Structure Determination of [Re(CO) 3 (tnen) (HzO)*'BFu- 139 5.5.1 Crystal Data 139 5.5.2 Structural Solution and Refinenent 140 5.5.3 Description of the Structure t42 5.6 A lsF N.M.R. study t47 5.6.1 tsF N.M.R. Spectra L47 5.6.2 Variable Temperature 1s F N.M.R. 150 1V Page s.7 Discussion 153 5.8 Experimental 155 CHAPTER 6 - CONCLUSION L57 6.1 Rhenium-Fluoride and -Oxygen Bond Lengths L57 6.2 Suggestions for Further Research 160 CHAPTER 7 - CRYSTALLOGRAPHY AI'ID EXPERIMENTAL 161 7.t Crystallography 161 7.t"L Instrumental 161 7.1.2 Conputing t64 7.2 Experimental L67 7.2.L General L67 7.2.2 Physical Measurements and Instrumentation L67 7.2.3 Gas, Ligands, Reagents and Solvents 169 7.2.4 Preparation of the Precursors L7T APPENDIX 1 - SELECTED SOLID STATE INFRARED SPECTRA t73 APPENDIX 2 - OÏHER POSSIBLE METAL CARBONYL FLUORIDE COMPLEXES L76 LIST OF PUBLICATIONS L79 REFERENCES 180 MICROFICHE The nicrofiche containing the hydrogen atomic paraneters and the tabulated structure factors are given at the end of the thesis. V SUMMARY Halogen abstraction reactions were investigated using manganese(I) and rheniun(I) carbonyl haLide (where, halide = Cl, Br) complexes as substrates during attenpts to coordinate fluoride or fluoro- and oxy-anion ligands. The preparative nethods developed were then applied to a selected ntmber of other transition metal carbonyl halide conplexes. The complexes Mn(CQ)sX (where, X = Cl, Br) react with thallitut fluoride and silver fluoride in dichloromethane solutions to give a mixture of the cluster species, [l{n(C0) s {Fx, (0H) r-x}] ,-. Similarly, rheniu¡n pentacarbonyl bromide reacts with silver fluoride in dichloro- methane and hexafluorobenzene to form the cubane-type cluster, [Re(C0)sF]q. These compounds have been characterízed by infrared, mass spectroscopy and crystal structure determinations. The clystal structures of the two complexes show that the fluoro or hydroxy groups are involved in Us-type bridging with the respective netals. When the manganese and rheniun pentacarbonyl complexes were reacted with silver bifluoride (AgFzH) in fluorinated solvents (CeHs, CsFe) using plastic reaction vessels the products formed were the anhydrous clusters, [NÍ(CO) 3F] 4 (where, M = Mn, Re). The rhodium cluster, [Rh(PPh3)Cl] 4 crystallizes from solution when the product of the reaction between Rh(CO)(PPhg)zCl and AgF2H is left in dichloromethane. However, with the use of dry hexafluorobenzene and plastic reaction vessels only the fluoride cluster, [Rh(PPh3)F]a was isolated. The reactions of the substituted rhenium carbonyl bromides, Re(CO)r(Lz)Br (where, Lz = bpy, diphos, 2PPh¡, tmen), with AgF2H in dichloronethane in plastic vessels yielded the anhydrous fluoride vi analogues. The complexes, Re(CO),(Lz)Br (where, Lz = bpy, tmen), react with AgF2H in dichloromethane or hexafl.uorobenzene in pyrex glass vessels to fonr the species, [Re(C0) g (Lz)F] zH.HOBFs. I{n(CO) 3 (diphos)C1 reacts with the [PhaAs]*¡HOnf rl- impurity in Ph'+AsF to forn fi\frr(CO) 3 (diphos) (HOBFa)ì. The trifluorohydroxy borate anion, IHOBF3]-, results fron a reaction involving AgF2H and the glass surfaces. All substituted rhenium fluoride complexes have been characterized by infrared and mass spectroscopy. While the species Re(C0)s(tnen)F, ll!fir(C0) 3 (diphos) (H0BFg)].1(dpeo) and [Re(C0) ¡(trnen)F] zH.HOBFs have also been characterized by their crystal structures. When Fe(C0)2CpI is treated with AgF2H decarboxylation products result which have not been characterized. Pentacarbonyl and substituted rheniu¡n bromide complexes react with AgAsF5 or AgBFa in dichloromethane to form the respective aquo species, [Re(CO) s(0Hz)]+Y- (where, Y = AsFe-, BF+-) and [Re(CO) s(Lz) (oHz)1+Br,*- (Lz = bpy, diphos, PPh3). These aquo complexes have been characterized by infrared and mass spectroscopy. In addition, the species, [Re(CO)s(Lz)(OH2)]+Y- (where, 1. Lz = 2(CO), Y = AsFe-, 2. L2 = tmen, Y = AsFe-, BF;), were also characterized by their crystal structures. lsF A nuclear magnetic resonance study of the [Re(CO)s(tmen)(HzO)1+'BF+- system has established that in solutíon (CDzClz) an equilibriun exists between the coordinated and I'free'r tetrafluoroborate anion, according to the following equation: + + BF+- Re(CO)3(tmen)FBF3 nzO =94.!f [Re(CO)3(tnen)(HzO)1+ Variable temperature IeN.M.R. spectroscopy has shown that this equilibrium is temperature dependant. The rhenium complexes Re(C0)g(bpy)FAsF5 and Re(C0)3(tnen)FBF3 formed when solutions (C6FIsF, CeFe) containing the corïesponding aquo-species were allowed to evaporate at ca. -10"C in a v11 dry nitrogen atmosphere over phosphorus pentoxide. The investigation presented in this thesis led to the facile pathway for the preparation of the respective fluoride complexes. The complexes were obtained by enploying relatively mild reagents conpared to fluorine gas, hydrogen fluoride and xenon hexafluorÍde. This was achieved when using (a) the right solvents, which were not susceptible to halide substitution reactions; (b) dry solvents, reaction atnosphere and fluorinating reagents; and (c) when using plastic reaction vessels. viii STATEMENT This thesis contains no material previóusly submitted for a degtee or diplona in any Universitl, a4d, to the best of the candidaters knowledge, contains no naterial previously published or written by another person' excePt where due reference is made in the text of this thesis. The author accepts futl responsibil.ity for any errors present in the treatise, regardless of their nature. Ernst Horn tx ACKNOl.lLEDGEMENTS I am sincerely grateful to rny supervisor, Dr.
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  • 1,1,1,2-Tetrafluoroethane (HFC-134A) (CAS No. 811-97-2) (Second Edition)

    1,1,1,2-Tetrafluoroethane (HFC-134A) (CAS No. 811-97-2) (Second Edition)

    1,1,1,2-Tetrafluoroethane (HFC-134a) (CAS No. 811-97-2) (Second Edition) JACC No. 50 ISSN-0773-6339-50 Brussels, January 2006 1,1,1,2-Tetrafluoroethane (HFC-134a) (CAS No. 811-97-2) (Second Edition) ECETOC JACC REPORT No. 50 © Copyright – ECETOC AISBL European Centre for Ecotoxicology and Toxicology of Chemicals 4 Avenue E. Van Nieuwenhuyse (Bte 6), B-1160 Brussels, Belgium. All rights reserved. No part of this publication may be reproduced, copied, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the copyright holder. Applications to reproduce, store, copy or translate should be made to the Secretary General. ECETOC welcomes such applications. Reference to the document, its title and summary may be copied or abstracted in data retrieval systems without subsequent reference. The content of this document has been prepared and reviewed by experts on behalf of ECETOC with all possible care and from the available scientific information. It is provided for information only. ECETOC cannot accept any responsibility or liability and does not provide a warranty for any use or interpretation of the material contained in the publication. ECETOC JACC No. 50 1,1,1,2-Tetrafluoroethane (HFC-134a) (CAS No. 811-97-2) (Second Edition) 1,1,1,2-Tetrafluoroethane (HFC-134a) (CAS No. 811-97-2) CONTENTS EXECUTIVE SUMMARY 1 THE ECETOC SCHEME FOR THE JOINT ASSESSMENT OF COMMODITY CHEMICALS 3 1. SUMMARY AND CONCLUSIONS 4 2. IDENTITY, PHYSICAL AND CHEMICAL PROPERTIES, ANALYTICAL METHODS 6 2.1 Identity 6 2.2 EU classification and labelling 6 2.3 Physical and chemical properties 6 2.4 Conversion factors 8 2.5 Analytical methods 8 3.