Carboranes (eBook)
1139 Seiten
Elsevier Science (Verlag)
978-0-08-092104-4 (ISBN)
Carboranes Second Edition is designed as a comprehensive source of information in a field that has experienced enormous growth in both its fundamental and applied aspects in the four decades since the publication of Carboranes (1970). During this long period thousands of original research papers have appeared, along with many review articles and book chapters dealing with aspects of carborane chemistry. As carborane science has grown in complexity, and applications have advanced steadily in areas such as medicine, nanostructured and electroactive materials, catalysis, polymers, and others, the need for a monograph covering the entire area in a unified treatment has become increasingly apparent. This volume has two principal objectives, the first of which is to provide a readable and concise introduction to the basic principles underlying the synthesis, structures, reactivity, and applications of carboranes and metallacarboranes at a level suitable for readers in industry and academe who are not trained in boron chemistry but find themselves working with, or lecturing about carboranes. Secondly, the book furnishes a trove of detailed information for workers active in carborane science and associated technologies. To that end, it incorporates tables listing thousands of specific compounds keyed to literature references (supplemented by additional information available on a website), together with more than 2,000 molecular structure drawings that illuminate the accompanying discussion. Thorough treatment of the synthesis, structures, and reactions of carboranes, heterocarboranes, and metallacarboranes in the first 13 chapters is followed by four chapters detailing advances in practical applications in polymer science, catalysis, medicine, and other areas.
- Includes over 2,000 molecular structure drawings throughout the text
- Features tables listing thousands of compounds with key literature references
- Extended and updated tables provided online via the book's website
Russell N. Grimes is Professor Emeritus of Chemistry at the University of Virginia, where he taught inorganic chemistry from 1963 to 2003 and mentored the research of 75 graduate students and postdoctoral associates as well as numerous undergraduates. He was a pioneer in the development of boron hydride and boron cluster chemistry and is author or co-author of over 240 peer-reviewed journal articles and review chapters. He has authored or edited four books, including 'Carboranes' (1970), 'Carboranes, Second Edition' (2011), 'Metal Interactions with Boron Clusters' (1982), and 'Inorganic Syntheses Volume 26' (1989), and wrote the chapter on Boron in 'Advanced Inorganic Chemistry, Sixth Edition' by Cotton, Wilkinson, Murillo, and Bochmann (1999). He is a native of Pennsylvania and earned a B.S. Chemistry degree at Lafayette College and a Ph.D. in Chemistry at the University of Minnesota, the research for which was conducted at Harvard University under the guidance of W N. Lipscomb followed by postdoctoral work under M. F. Hawthorne at the University of California at Riverside. He has been a Senior Fulbright Scholar at the University of Canterbury in New Zealand, a Humboldt Scholar and Guest Professor at Heidelberg University in Germany, and a Visiting Scholar at the Korea Advanced Institute for Science and Technology. He is a six-time American Chemical Society Tour Speaker and is a Fellow of the American Association for the Advancement of Science.
Carboranes, Second Edition is designed as a comprehensive source of information in a field that has experienced enormous growth in both its fundamental and applied aspects in the four decades since the publication of Carboranes (1970). During this long period thousands of original research papers have appeared, along with many review articles and book chapters dealing with aspects of carborane chemistry. As carborane science has grown in complexity, and applications have advanced steadily in areas such as medicine, nanostructured and electroactive materials, catalysis, polymers, and others, the need for a monograph covering the entire area in a unified treatment has become increasingly apparent.This volume has two principal objectives, the first of which is to provide a readable and concise introduction to the basic principles underlying the synthesis, structures, reactivity, and applications of carboranes and metallacarboranes at a level suitable for readers in industry and academe who are not trained in boron chemistry but find themselves working with, or lecturing about carboranes. Secondly, the book furnishes a trove of detailed information for workers active in carborane science and associated technologies. To that end, it incorporates tables listing thousands of specific compounds keyed to literature references, together with more than 2,000 molecular structure drawings that illuminate the accompanying discussion. Thorough treatment of the synthesis, structures, and reactions of carboranes, heterocarboranes, and metallacarboranes in the first 13 chapters is followed by four chapters detailing advances in practical applications in polymer science, catalysis, medicine, and other areas. Includes over 2,000 molecular structure drawings throughout the text Features tables listing thousands of compounds with key literature references
Cover 1
Carboranes 4
Copyright 5
Dedication 6
Contents 8
Preface 18
Chapter 1: Introduction and History 20
References 24
Chapter 2: Structure and Bonding 26
2.1. General perspective 26
2.2. Nomenclature and numbering 26
2.3. The localized-bond approach 27
2.4. Structural patterns in boron clusters 28
2.5. Extensions of the electron-counting rules 33
2.6. Electron-counting in classically bonded clusters 34
2.7. Isomer stability and cage rearrangement 35
2.8. Cluster aromaticity 35
2.9. ''Electron Deficiency" in Polyhedral Boron Clusters 36
References 37
Chapter 3: Synthesis and Reactivity: An Overview 40
3.1. General preparative routes to carboranes 40
3.1.1. Borane-alkyne gas phase reactions 40
3.1.2. Borane-alkyne reactions in solution 41
3.1.3. Carborane-alkyne reactions 41
3.1.4. Carbon insertion via cyano- and isocyanoboranes 41
3.1.5. Carboranes from organoboranes 41
3.2. Interconversion Reactions 42
3.2.1. Polyhedral rearrangement 42
3.2.2. Metal-promoted cage fusion 42
3.2.3. Polyhedral expansion and contraction 42
3.3. Substitution at cage carbon and boron atoms 43
3.4. Carboranes as Substituents and Ligands 44
Chapter 4: Small carboranes: Four- to six-vertex clusters 46
4.1. Overview 46
4.2. 4-Vertex open clusters 46
4.2.1. CB3Hx and C2B2Hx 46
4.3. 5-Vertex open clusters 47
4.3.1. Nido- and arachno-CB4 systems 47
4.3.2. Nido-1,2-C2B3H7 48
4.3.3. Other open-cage C2B3 clusters 51
4.3.4. Nido-C3B2 clusters 51
4.4. 5-Vertex Closo clusters 52
4.4.1. CB4Hx 52
4.4.2. 1,5-C2B3H5 52
4.4.3. Closo-C3B2H5+ 60
4.5. 6-Vertex open clusters 60
4.5.1. Nido-2-CB5H9 60
4.5.2. Hypho-CB5H13 63
4.5.3. Nido-2,3-C2B4H8 64
4.5.4. Nido-2,4-C2B4H8 75
4.5.5. Arachno- and hypho-C2B4Hx clusters 78
4.5.6. Nido-2,3,4-C3B3H7 79
4.5.7. Nido-2,3,5-C3B3H7 81
4.5.8. Nido-2,3,4,5-C4B2H6 83
4.5.9. Nido-2,3,4,5,6-C5BH6+ 91
4.6. 6-Vertex closo clusters 92
4.6.1. 1-CB5H7 and 1-CB5H6- 92
4.6.2. 1,2- and 1,6-C2B4H6 94
References 102
Chapter 5: Intermediate carboranes: Seven- to nine-vertex clusters 112
5.1. Overview 112
5.2. 7-Vertex open clusters 112
5.2.1. Nido-C2B5H8- 112
5.3. 7-Vertex Closo clusters 113
5.3.1. 2-CB6H7- 113
5.3.2. 2,3-C2B5H7 115
5.3.3. 2,4-C2B5H7 118
5.3.4. C3B4 clusters 130
5.4. 8-Vertex open clusters 130
5.4.1. Arachno-CB7H13 and CB7H12- 130
5.4.2. Nido-C2B6H10 131
5.4.3. Nido-C2B6H82- 133
5.4.4. Arachno-C2B6H12 134
5.4.5. Hypho-C2B6H13- 135
5.4.6. Nido-C3B5H9 135
5.4.7. Nido-C4B4H8 135
5.5. 8-Vertex Closo clusters 139
5.5.1. CB7H8- 139
5.5.2. 1,7-C2B6H8 140
5.6. 9-Vertex open clusters 143
5.6.1. Nido-CB8H12, arachno-CB8H14, and arachno-CB8H13- 143
5.6.2. Nido-C2B7H11 146
5.6.3. Arachno-C2B7H13 146
5.6.4. Hypho-C3B6H13- 152
5.7. 9-Vertex Closo clusters 153
5.7.1. 4-CB8H9- 153
5.7.2. 4,5-C2B7H9 153
References 156
Chapter 6: Ten-vertex carboranes 164
6.1. Overview 164
6.2. 10-Vertex open clusters 164
6.2.1. Nido-CB9H12- and arachno-CB9H14- 164
6.2.2. Nido-C2B8H12 168
6.2.3. Arachno-C2B8H14 174
6.2.4. Nido-C3B7H11 and arachno-C3B7H13 177
6.2.5. Nido-C4B6H10 180
6.2.6. Arachno-C4B6H12 181
6.3. 10-Vertex closo clusters 181
6.3.1. 1- and 2-CB9H10- 181
6.3.2. C2B8H10 190
References 200
Chapter 7: Eleven-vertex carboranes 206
7.1. Overview 206
7.2. 11-Vertex open clusters 206
7.2.1. Nido-CB10H13- 206
7.2.2. Nido-C2B9H13, nido-C2B9H12-, and nido-C2B9H112- 216
7.2.3. Nido-C3B8H12 and nido-C3B8H11- 258
7.2.4. Nido-C4B7H11 263
7.2.5. Arachno-C4B7H13 264
7.3. 11-Vertex closo clusters 265
7.3.1. Closo-CB10H11- 265
7.3.2. Closo-C2B9H11 267
References 273
Chapter 8: Icosahedral carboranes: Closo-CB11clusters 286
8.1. Overview 286
8.2. Synthesis and structure 286
8.2.1. Parent CB11H12- 286
8.2.2. Substitution at carbon 302
8.2.3. Substitution at boron by electrophilic reagents 303
8.2.4. Synthesis of B-substituted derivatives via boron insertion 305
8.2.5. Polyhalogenation at boron 305
8.2.6. Polyalkylation at boron 306
8.2.7. Mixed alkyl-halo derivatives 307
8.2.8. Acid-base properties 308
8.2.9. Metal complexation 309
8.2.10. Special properties of CB11Me12-, HCB11Me11-, and CB11Me12 312
References 313
Chapter 9: Icosahedral carboranes: 1,2-C2B10H12 320
9.1. Overview 320
9.2. Synthesis of the 1,2-C2B10 cage 320
9.2.1. From B10H14 320
9.2.2. From BH4- salts 395
9.2.3. Boron addition to 11-vertex nido-carboranes 395
9.2.4. Other o-Carborane-forming reactions 395
9.3. Structure and properties 395
9.4. Substitution at carbon 396
9.4.1. Metallation with Group 1 and 2 metals 396
9.4.2. Substitution via C-metallated carboranes 400
9.4.3. Substitution at carbon without metallation 413
9.5. Substitution at boron 414
9.5.1. Indirect routes to B-substituted derivatives 414
9.5.2. Direct substitution on o-carboranyl boron atoms 415
9.5.3. Addition of transition metals at boron 423
9.5.4. Metal-promoted cross-coupling of B-halo-o-carboranes 424
9.6. Alkyl, haloalkyl, and aryl derivatives 425
9.6.1. Properties of Alkyl and Haloalkyl derivatives 425
9.6.2. Properties of Aryl derivatives 425
9.7. Alkenyl and alkynyl derivatives 430
9.7.1. Properties of Alkenyl derivatives 430
9.7.2. Properties of Alkynyl derivatives 436
9.8. Carboxylic acids and esters 437
9.8.1. Synthesis of carboxylic acids 437
9.8.2. Properties of o-carboranyl carboxylic acids 444
9.9. Alcohols, hydroxy derivatives, and ethers 446
9.9.1. Synthesis 446
9.9.2. Reactions of alcohols and ethers 453
9.10. Aldehydes and ketones 454
9.10.1. Synthesis of aldehydes 454
9.10.2. Synthesis of ketones 455
9.10.3. Reactions of o-carboranyl aldehydes and ketones 459
9.11. Silicon derivatives 461
9.11.1. C-silyl derivatives 462
9.11.2. B-organosilyl derivatives 473
9.12. Germanium, tin, and lead derivatives 473
9.12.1. C-germyl and C-stannyl derivatives 473
9.12.2. B-stannyl derivatives 479
9.12.3. C-plumbyl derivatives 480
9.13. Nitrogen derivatives 480
9.13.1. Nitrato, nitro, and related compounds 480
9.13.2. Amines, azides, and diazonium salts 482
9.13.3. Nitrogen heterocycles 486
9.13.4. Amides and imides 490
9.13.5. Nitriles, isonitriles, and isocyanates 490
9.13.6. Carbamates and ureas 492
9.14. Phosphorus, arsenic, antimony, and bismuth derivatives 494
9.14.1. Phosphino and related derivatives 494
9.14.2. Phosphates, phosphites, and related derivatives 497
9.14.3. Thiophosphites and thiophosphates 500
9.14.4. Cyclotriphosphazenes 502
9.14.5. Metal complexes 503
9.14.6. Cage-opening reactions 506
9.15. Sulfur, selenium, and tellurium derivatives 507
9.15.1. Thiols, thioethers, disulfides, and related compounds 507
9.15.2. Metal complexes 514
9.16. Halogen derivatives 520
9.16.1. Synthesis 520
9.16.2. Properties of B-decahalo-o-carboranes 520
9.16.3. Properties of partially B-halogenated o-carboranes 521
9.16.4. Properties of C-halo-o-carboranes 524
9.16.5. Properties of C-halomethyl-o-carboranes 525
9.17. Mercury derivatives 525
References 527
Chapter 10: Icosahedral carboranes: 1,7-C2B10H12and 1,12-C2B10H12 560
10.1. Overview 560
10.2. Synthesis and structure 560
10.2.1. m-Carborane 560
10.2.2. p-Carborane 622
10.3. Cage rearrangement mechanisms 623
10.4. "Reverse isomerization": 1,12- rarr 1,7- rarr 1,2-C2B10H12 625
10.5. Substitution at carbon 626
10.5.1. Metallation with Group 1 and 2 metals 626
10.5.2. Substitution via C-metallated carboranes 627
10.6. Substitution at boron 636
10.6.1. Boron insertion into nido-C2B9 dianions 636
10.6.2. Nucleophilic displacement 636
10.6.3. Electrophilic alkylation 636
10.6.4. Electrophilic halogenation 637
10.6.5. Photochemical (radical) halogenation 638
10.6.6. Fluorination 638
10.6.7. Addition of main-group elements and mercury at boron 639
10.6.8. Addition of transition metals at boron 641
10.6.9. Organosubstitution at boron 641
10.7. Alkyl, haloalkyl, and aryl derivatives 644
10.7.1. Properties of alkyl- and haloalkyl-substituted m- and p-carboranes 644
10.7.2. Properties of aryl-substituted m- and p-carboranes 644
10.8. Alkenyl and alkynyl derivatives 647
10.8.1. Reactions and electronic properties 647
10.9. Carboxylic acids and esters 650
10.9.1. Synthesis 650
10.9.2. Properties of m- and p-carboranyl carboxylic acids 651
10.10. Alcohols, hydroxy derivatives, and ethers 654
10.10.1. Synthesis 654
10.10.2. Properties of m- and p-carboranyl alcohols 656
10.11. Aldehydes and ketones 657
10.11.1. Synthesis 657
10.11.2. Properties 658
10.12. Silicon, germanium, tin, and lead derivatives 659
10.12.1. Synthesis 659
10.12.2. Properties 660
10.13. Nitrogen derivatives 660
10.13.1. Nitro, nitrito, and related compounds 661
10.13.2. Amines, azides, and diazonium salts 661
10.13.3. Nitrogen heterocycles 663
10.13.4. Amides and imides 665
10.13.5. Nitriles, isonitriles, and isocyanates 665
10.13.6. Ureas 666
10.14. Phosphorus derivatives 667
10.14.1. Synthesis 667
10.14.2. Properties 667
10.15. Sulfur, selenium, and tellurium derivatives 669
10.15.1. Synthesis 669
10.15.2. Properties 671
10.16. Halogen derivatives 672
10.16.1. Synthesis and properties 672
10.16.2. C-halo derivatives 672
10.16.3. B-halo derivatives 672
References 675
Chapter 11: Open 12-vertex and supra-icosahedral carboranes 694
11.1. Overview 694
11.2. Open-cage C2B10 anions 694
11.2.1. Reduction of neutral C2B10 icosahedra 694
11.2.2. Carbon-bridged clusters 701
11.3. Nido- and arachno-C4B8 carboranes 703
11.3.1. Synthesis of Nido-C4B8 cages 704
11.3.2. Structure and fluxional behavior of C4B8 clusters 707
11.3.3. Metal complexation of Nido-R4C4B8H8 carboranes 708
11.3.4. Formation and properties of Arachno-R4C4B8H8n- mono- and dianions 708
11.3.5. Synthesis of neutral Arachno-C4B8 clusters 710
11.3.6. Deboronation of Nido-C4B8 cages 710
11.3.7. General observations 711
11.4. Arachno-C6B6 carboranes 711
11.5. Supra-icosahedral carboranes 711
11.5.1. 13-vertex C2B11 and 14-vertex C2B12 clusters 711
References 716
Chapter 12: Heteroatom carboranes of the main group elements 720
12.1. Overview 720
12.2. Heterocarboranes of the group 1 and 2 elements 720
12.2.1. Lithium, sodium, potassium, and rubidium 720
12.2.2. Beryllium, magnesium, calcium, strontium, and barium 724
12.3. Heterocarboranes of the group 13 elements 726
12.3.1. Aluminum 729
12.3.2. Gallium and indium 733
12.3.3. Thallium 736
12.4. Heterocarboranes of the group 14 elements 737
12.4.1. Silicon 743
12.4.2. Germanium 744
12.4.3. Tin and lead 747
12.5. Heterocarboranes of the group 15 elements 751
12.5.1. Nitrogen 751
12.5.2. Phosphorus 754
12.5.3. Arsenic and antimony 774
12.6. Heterocarboranes of the group 16 elements 777
12.6.1. Sulfur and selenium 780
References 785
Chapter 13: Metallacarboranes of the transition and lanthanide elements 792
13.1. Overview 792
13.2. General synthetic methods 792
13.2.1. Insertion of metal cations into Open-cage carborane anions 792
13.2.2. Insertion of metals into neutral carboranes 828
13.2.3. Insertion of hydrocarbons into metallaboranes 828
13.2.4. Polyhedral expansion and contraction 830
13.2.5. Oxidative fusion 831
13.2.6. Metal displacement and transfer 832
13.2.7. Metal atom reactions 833
13.2.8. Other routes to metallacarboranes 833
13.3. Six- and seven-vertex metallacarboranes 834
13.3.1. Closo six-vertex cages 834
13.3.2. Synthesis of closo-MC2B4 cages 834
13.3.3. Functionalization and linkage of Closo-LMC2B4 and Nido-LMC2B3 clusters 836
13.3.4. Metal-metal communication in linked MC2B4 clusters 841
13.3.5. Thermal rearrangement of seven-vertex metallacarboranes 841
13.3.6. Small metallacarboranes in organic synthesis 842
13.3.7. Nido-MC2B3 and Closo-M2C2B3 cages 847
13.3.8. Nido-MC3B2 and Closo-M2C3B2 cages 852
13.4. Eight- to eleven-vertex metallacarboranes 858
13.4.1. Monocarbon cages 858
13.4.2. Dicarbon cages 887
13.4.3. Tricarbon cages 897
13.4.4. Tetracarbon clusters 899
13.5. Twelve-vertex metallacarboranes 901
13.5.1. Monocarbon clusters 901
13.5.2. Dicarbon clusters 970
13.5.3. Tricarbon clusters 980
13.5.4. Tetracarbon and pentacarbon clusters 982
13.6. Supraicosahedral metallacarboranes 984
13.6.1. Dicarbon 13-vertex clusters 984
13.6.2. Carbon-rich 13- and 14-vertex clusters 1000
References 1003
Chapter 14: Carborane polymers and dendrimers 1034
14.1. Overview 1034
14.2. Polymers of subicosahedral closo-carboranes 1034
14.3. Polymers of open-cage carboranes 1035
14.4. Polymers of closo-CB11 carboranes 1035
14.5. Polymers of closo-C2B10 carboranes 1035
14.5.1. Systems with carborane units in the polymeric chain 1036
14.5.2. Polymers with pendant carboranes 1042
14.6. Metallacarborane polymers 1045
14.6.1. Metallation of Nido-carboranyl polymers 1046
14.6.2. Metallacarborane dendrimers 1046
14.6.3. Polymerization of metallacarborane monomers 1048
14.6.4. Metallacarboranes as dopants and inclusion compounds in polymeric materials 1050
References 1050
Chapter 15: Carboranes in catalysis 1056
15.1. Overview 1056
15.2. Non-metallated carboranes as catalytic agents 1056
15.3. Closo-CB11 anions in catalysis 1056
15.3.1. Salts with main group metal cations 1056
15.3.2. Salts with transition metal-containing cations 1057
15.4. Exo-metallated carboranes in catalysis 1058
15.4.1. Closo-carborane systems 1058
15.4.2. Nido-carborane systems 1061
15.5. Metallacarboranes in catalysis 1063
15.5.1. Subicosahedral clusters 1063
15.5.2. Icosahedral clusters 1064
15.5.3. Supraicosahedral clusters 1068
References 1068
Chapter 16: Carboranes in medicine 1072
16.1. Overview 1072
16.2. Carboranes in drug development 1072
16.2.1. Carboranes as pharmacophores 1072
16.2.2. HIV Protease inhibitors 1076
16.2.3. Anticoagulants 1077
16.2.4. Antitumor agents 1077
16.3. Boron Neutron Capture Therapy 1081
16.3.1. Background 1081
16.3.2. Approaches to BNCT 1082
16.3.3. Small-molecule boron delivery agents 1082
16.3.4. High molecular weight boron delivery agents 1085
16.4. Boron Neutron Capture Synovectomy 1089
16.5. Photodynamic Therapy 1089
16.6. Carboranes in Molecular Imaging and Radiotherapy 1090
16.6.1. Radiohalogenation 1090
16.6.2. Radioastatination 1091
16.6.3. Radiometal labeling 1092
16.6.4. Gadolinium in imaging and therapy 1092
16.6.5. Other carborane-based imaging methods 1093
References 1093
Chapter 17: Carboranes in other applications 1102
17.1. Overview 1102
17.2. Metal ion extraction 1102
17.3. Carborane-based materials 1104
17.3.1. Ionic liquids 1104
17.3.2. Liquid crystals 1104
17.3.3. Nonlinear optical materials 1105
17.3.4. Electroactive systems 1107
17.3.5. Networks and supramolecular assemblies 1110
17.3.6. Gas separation and storage materials 1112
17.3.7. Films and monolayers 1113
17.3.8. Carboranes in biomaterials 1114
17.3.9. Carborane-based ceramics 1114
17.4. Molecular machines 1115
17.5. Carboranes as noncatalytic synthetic agents 1117
17.6. Carboranes in analysis 1118
17.6.1. Gas chromatography 1118
17.6.2. Ion-selective electrodes 1118
17.7. Into the future 1119
References 1119
Index 1126
| Erscheint lt. Verlag | 6.5.2011 |
|---|---|
| Sprache | englisch |
| Themenwelt | Sachbuch/Ratgeber |
| Naturwissenschaften ► Biologie | |
| Naturwissenschaften ► Chemie ► Anorganische Chemie | |
| Naturwissenschaften ► Chemie ► Organische Chemie | |
| Technik | |
| ISBN-10 | 0-08-092104-3 / 0080921043 |
| ISBN-13 | 978-0-08-092104-4 / 9780080921044 |
| Haben Sie eine Frage zum Produkt? |
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