Organometallic Compounds of Nickel, Palladium, Platinum, Copper, Silver and Gold PDF
Preview Organometallic Compounds of Nickel, Palladium, Platinum, Copper, Silver and Gold
Organometallic Compounds of Nickel, Palladium, Platinum, Copper, Silver and Gold Organometallic Compounds of Nickel, Palladium, Platinum, Copper, Silver and Gold Edited by R. J. Cross University of Glasgow and D. M. P. Mingos University of Oxford SPRINGER-SCIENCE+BUSINESS MEDIA, B.V. ISBN 978-1-4613-7478-7 ISBN 978-1-4615-5427-1 (eBook) DOI 10.1007/978-1-4615-5427-1 © 1985 Springer Science+Business Media Dordrecht Originally published by Chapman and Hall Ltd in 1985 AH rights reserved. No part of this book may be reprinted, or reproduced or uti1ized in any form by any electronic, mechanica1 or other means, now known or hereafter invented, including photocopying and recording, or in any information storage or retrieva1 system, without permis sion in writing from Springer-Science+Business Media, B.V .. Library of Congress Cataloging in Publication Data Main entry under title: Organometallic compounds of nickel, British Library Cataloguing in palladium, copper, silver, and gold. Publication Data lncludes index. Organometallic compounds of nickel, 1. Organometallic compounds - palladium, platinum, copper, silver and Handbooks, manuals, etc. gold. 1. Cross, R.J., 1941- II. Mingos, 1. Organometallic compounds D.M.P.,1944-. III. Series. 1. Crbss, R.J. II. Mingos, D.M.P. QD41 1. '72 1985 547' .05 84-29346 547' .05 QD411 ISBN 978-1-4613-7478-7 ISBN 978-1-4613-7478-7 Contents Preface pagevll Introduction IX Ag Silver 1 Au Gold 9 Cu Copper 25 Ni Nickel 39 Pd Palladium 101 Pt Platinum 163 Name Index 245 Molecular Formula Index 277 CAS Registry Number Index 315 v This Sourcebook has been reproduced in part from the Dictionary of Organometallic Compounds. If you find it useful and you would like full coverage, then why not buy the Main Work for your library DICTIONARY OF a GANOMETALLIC COMPOUNDS The recent growth in organometallic chemistry has led to an explosion in the number of organometa])ic compounds discovered or synthesized. How can scientists working in this area locate reliable data on all really important organometallic? The answer lies in the new Dictionary of OrganometalJic Compounds, pubJi hed in November 1984. • provides within 15,000 Entries an extensive • provides a continually up-to-date information yet selective compilation of the most important system with Annual Supplements organometallic compounds • entries compiled by subject experts under • for each compound, details of structure, supervision of a prestigious international . physical and chemical properties, reactions and advisory board references are provided in clearly set out and • a time-saving, cost-saving and reliable easily scanned Entries resource essential to all users of organometallic • offers access to compounds by structure, compounds molecular formula, chemical name, or CAS Registry Number From a review by F.A. Cotton, Texas A & M • the structure index contains reduced images University of all the structure diagrams in the section - a 'This extraordinarily useful compendium is unique feature which allows users to 'browse', one that no chemical enterprise having the and to appreciate quickly the full range of types slightest involvement in organometallic of compounds which have been synthesized chemistry would want to be (or would be wise to be) without.' Publication date: November 1984 ISBN: 0 412 24710 0 286 x 213mm 3,000 pages in three volumes For further information please write to The Promotion Department, Chapman and Hall, 11 New Fetter Lane, London EC4P 4EE. S CHAPMAN AND HALL 11 New Fetter Lane, London EC4P 4EE 733 Third Avenue, New York NY 10017 Preface This is one of the first volumes to be published in the series of Chapman and Hall Chemistry Sourcebooks which provides carefully tailored information to workers in specialized areas of chemistry. The information contained in this book is derived from the Dictionary of Organometallic Compounds, published in November 1984. The organic compounds of the six metals in this volume are of great interest both to inorganic and organic chemists. Organonickel and organopalladium compounds are frequently used as selective reagents in synthesis and as catalysts for organic reactions. Organoplatinum compounds, however, are generally slower to react and lend themselves to mechanistic studies. A vast range of such compounds has been prepared. Whilst organometallics of the gold triad are fewer, they display a range of interesting structures , and organocopper compounds are widely used synthetic reagents. It is therefore anticipated that this particular compendium will reach a wide readership. The databank on the properties of organometallic compounds, which is represented in its current form by the Dictionary of Organometallic Compounds and its subset publications such as this volume, will be kept continuously up-to-date. Supplements to the main Dictionary will appear annually and revised editions of this Sourcebook will be published from time to time as demands permits. RJ. Cross D.M.P. Mingos VII Introduction 1. Using the Sourcebook (2) Any compound with an established use, such as in catalysis, as a synthetic reagent or starting material. The Sourcebook is divided into element sections: (3) Other compounds of particular chemical, within each section the arrangement of entries is in structural, biological or historical interest, especially order of molecular formula according to the Hill those thought to exhibit unusual bonding characteris convention (i.e. C, then H, then other elements in tics. alphabetical sequence of element symbol; where no carbon is present, the elements including Hare Some compounds which are not considered ordered strictly alphabetically). sufficiently important to justify separate entries of Every entry is numbered to assist ready location their own have been included as derivatives in the and the entry number consists of a metal element entries of other compounds. These may include for symbol followed by a five-digit number. example: (1) Organic derivatives in the classical sense. Indexes (2) Donor-acceptor complexes. There are three printed indexes: a name index which (3) The various salts of an anion or cation. In lists every compound name or synonym in alpha nearly every case, the entry for an ionic substance betical order; a molecular formula index which lists refers to the naked anion or cation, and the molecular all molecular formulae, including those of deriva formula, molecular weight and CAS registry number tives, in Hill convention order; and a CAS registry given for the main entry are those of the ion, in number index listing all CAS numbers included in the agreement with current CAS practice. Salts of the ion Sourcebook in serial order. All indexes refer to the with various counterions are then treated as entry number. In the name index an entry number derivatives and the molecular formulae of all of these which follows immediately upon an index term means are given. that the term itself is used as the entry name but an (4) Oligomeric compounds. Where a compound is entry number which is preceded by the word 'see' known in several states of molecular aggregation means that the term is a synonym to an entry name. In these are all included in the one entry, which usually all three indexes an entry number which is preceded refers to the monomer. Compounds which are known by the word 'in' refers the reader to a specified only in dimeric form are entered as such, but the stereoisomer or derivative which is to be found hypothetical monomers are included as derivatives to embedded within the particular entry. ensure that the names and molecular formulae of the In addition to the three printed indexes, each monomeric forms occur in the indexes. element section is preceded by a graphical structure index allowing the rapid visual location of compounds All names and molecular formulae recorded for of interest. The structure index reproduces all derivatives occur in the Name and Molecular structure diagrams present in that element section in Formula Indexes respectively. reduced size and printed in entry number order. The following paragraphs summarize important considerations in compiling the information in this 3. Chemical Names and Synonyms Sourcebook. For more detailed information, see the The naming of organometallic compounds is Introduction to the Dictionary of Organometallic frequently problematic and so in selecting the range Compounds from which this Sourcebook derives. of alternative names to present for each compound or derivative, editorial policy has been to report names 2. Compound Selection which are found in the literature, including Chemical Abstracts, and not to attempt to impose a system of In compiling this Sourcebook the aim has been to nomenclature. The editorial generation of new include from the primary literature up to mid 1983: names has therefore been kept to a minimum (1) Compounds representative of all important required by consistency. Most names given in the structural types (typically, the parent member of each Sourcebook are those given in the original paper( s) series, where known, together with a selection of its and in Chemical Abstracts. homologues). Names corresponding to those used by CAS during ix Introduction the 8th, 9th, and 10th collective index periods book represents the most complete and up to date (1967-71, 1972-6 and 1977-81 respectively) are review of the whole subject. In addition to sections labelled with the suffixes 8CI, 9CI and lOCI for each element there are chapters on the use of respectively. organometallics in organic synthesis and catalysis. Comprehensive Inorganic Chemistry, Trotman Dickenson, A.F. etal. Eds, Pergamon, Oxford, 1973. 4. Toxicity and Hazard Information Contains information about organometallics as well Toxicity and hazard information is highlighted by the as discussions of oxidation states, coortlination sign [> which also appears in the indexes. chemistry and analysis of the metals. Gmelins Handbuch der Anorganischen Chemie, All organometallic compounds should be treated as if 8th Edn, Springer-Verlag, Berlin. Some volumes of they have dangerous properties. Gmelin covering organometallic compounds have The information contained in the Sourcebook has been updated relatively recently and can therefore be been compiled from sources believed to be reliable. consulted for comprehensive data on some types of No warranty, guarantee or representation is made by organometallics. Some Gmelin element sections, the Publisher as to the correctness or sufficiency of however, are many years out of date. any information herein, and the Publisher assumes no Houben-Weyls Methoden der Organischen Che responsibility in connection therewith. mie, 4th Edn, Band XIII, Metallorganische Verbin The specific information in this publication on the dungen, Thieme-Verlag, Stuttgart. hazardous. and toxic properties of certain compounds The Chemistry of the Carbon-Metal Bond, Hartley, is intended to alert the reader to possible' dangers F.R. and Patai, S. Eds, Wiley, New York, 1982-. associated with the use of those compounds. The Contains sections on the synthesis, analysis and absence of such information should not,'however, be thermochemistry of various classes of organometallic taken as an indication of safety in use or misuse. compounds. Transition-Metal Complexes of Phosphorus, Arsenic and Antimony Ligands, McAuliffe, C.A. Ed., Macmillan, London, 1973. 5. Bibliographic References Methods of Elemento-Organic Chemistry, Koches The selection of references is made with the aim of' hkov, K.A. Ed., North Holland, Amsterdam, 1967. facilitating entry into the literature for the user who MTP International Review of Science: Inorganic wishes to locate more detailed information about a Chemistry, Series 2, Emeleus, H.J. Ed., Butter particular compound. Reference contents are fre worths, London; University Park Press, Baltimore, quently indicated using mnemonic suffixes. In 1974-5. general recent references are preferred to older ones, Advances in Organometallic Chemistry, Academic and the number of references quoted does not Press,1964-. necessarily indicate the relative importance of a Annual Surveys of Organometallic Chemistry, compound. Elsevier, 1964-7. Journal abbreviations generally follow the practi<:e Organometallic Chemistry Reviews, Elsevier, of Chemical Jtbstracts Service Source Index (CASSI). 1966-7. In patent references, no distinction is made between Organometallic Chemistry Reviews, Section A: patent applications and granted patents. Subject Reviews 1968-72. Organometallic Chemistry Reviews, Section B: Annual Surveys 1968-74. Journal of Organometallic Chemistry: This incor 6. Sources of Further Information porates reviews and surveys after the discontinuation The following books and review series provide more of the two series of Organometallic Chemistry information about various aspects of organometallic Reviews. chemistry. Lists of reviews specific to organic Organometallic Chemistry, 1972-, (Specialist compounds of particular metals may be found in the Periodical Reports), RSC. introductory sections of the metals concerned. Coordination Chemistry Reviews, Elsevier, 1966-. Progress in Inorganic Chemistry, Interscience, General 1959-. Comprehensive Organometallic Chemistry, Wilkin Advances in Inorganic Chemistry and Radio son, G. et af. Eds, Pergamon, Oxford, 1982. This chemistry, Academic Press, 1959-. x Introduction Analysis BC NMR Data for Organometallic Compounds, Mann, B.E. and Taylor, B.F. Eds, Academic Press, Scott's Standard Methods of Chemical Analysis, London, 1981. Furman, N.H. Ed., 6th Edn, Van Nostrand, New Spectroscopic Properties of Inorganic and Organo York,1962. metallic Compounds, 1968-, (Specialist Periodical Crompton, T.R., Chemical Analysis of Organo metallic Compounds, Academic Press, London, Reports), RSC. 1973. Handling Spectroscopy Shriver, D.F., The Manipulation of Air-Sensitive Compounds, McGraw-Hill, 1969. Nuclear Magnetic Resonance Spectroscopy of Nuclei Organometallic Syntheses, Academic Press, New Other than the Proton, Axenrod, T. and Webb, G.A. York, 1965, Vol.l. Eds, Wiley, London, 1974. NMR and the Periodic Table, Harris, R.K. and Mann, B.E. Eds, Academic Press, London, 1978. xi Ag Silver D. M. P. Mingos Argent (Fr.), Silber (Ger.), Plata (Sp.), Argento (Ital.), Cepe6po (Sierebro) (Russ.), ~ (Japan.) Atomic Number. 47 Spectroscopy. 107 Ag, I = 1, and 109 Ag, I = ~, are rather in sensitive nuclei with large Tl'S; however there have been some Atomic Weight. 107.868 reports of the use of 109 Ag nmr for organometallic com Electronic Configuration. [Kr 14 dlO 5s 1 pounds. Oxidation States. Ag(I) is the commonest oxidation state for Analysis. EDT A titrations with disodium ethylbis(5-tetra organometallic and related compounds, but Ag(II) and Ag(III) zolylazo)acetate as indicator. compounds are also known. References. In addition to references listed in the introduction Coordination Number. Ag(I) compounds are typically linear, to the Sourcebook, the following provide further reading: trigonal or tetrahedral, whilst those of Ag(II) are planar and Godensky, L. M. et aI., Engelhardt Tech. Bull., 1969,9, those of Ag(III) are planar or octahedral. 117 (thermodynamic data) Colour. Most organosilver(l) compounds are colourless with Hartley, F. R., Chem. Rev., 1973,73,163 (olefin and the exception of the highly coloured cluster compounds. Or acetylene complexes) ganosilver(III) compounds are commonly yellow. Singleton, E., J. Organomet. Chem., 1978, 158, 413 (organometallic chemistry) AfaiIability. Readily available starting materials include silver Bruce, M. I., J. Organomet. Chem., 1972,44,209 powder, Ag2C03, AgSbF6, AgN03, AgOAc, AgBF4, AgC104, (carbonyl compounds) all of which are moderately expensive. Henrichs, P. M. et al., J. Am. Chem. Soc., 1979,101,3222 Handling. Organosilver compounds do not require any special (nmr) handling techniques. Isotopic Abundance. 107 Ag, 51.82%; 109Ag, 48.18%. 1
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