Schiff bases are compounds created from a condensed amino compounds, which frequently form complexes with metal ions. They have diverse applications in biology, catalysis, material science and industry. Understanding these compounds, their properties, and the available methods for synthesizing them is a key to unlocking industrial innovation.
Schiff Base Metal Complexes provides a comprehensive overview of these compounds. It introduces the compounds and their properties before discussing their various synthesizing methods. A survey of existing and potential applications gives a complete picture and makes this a crucial guide for researchers and industry professionals looking to work with Schiff base complexes.
Schiff Base Metal Complexes readers will also find: - A systematic and organized structure designed to make information instantly accessible - Detailed coverage of thermal synthesis, photochemical synthesis, and more - Challenges with different methods described in order to help readers make the correct choice for their own work
Schiff Base Metal Complexes is a useful reference for organic chemists, materials scientists, and researchers or industry professionals working with organometallics.
Table of Contents
Preface xi
Part I Introduction 1
1 Historical Background 3
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
1.1 Introduction 3
1.2 Theories of Coordinate Bond 4
1.2.1 Valence Bond Theory 4
1.2.2 Crystal Field Theory 4
1.2.3 Molecular Orbital Theory 5
1.2.4 Ligand Field Theory 6
References 7
2 Classification 9
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
2.1 Ligands 9
2.2 Schiff Base 9
2.3 Types of Schiff Base 12
2.3.1 Salen-type Ligands 12
2.3.2 Salophen-type Ligands 12
2.3.3 Hydrazone-type Ligands 12
2.3.4 Thiosemicarbazone/Carbazone-type Ligands 13
2.3.5 Heterocyclic Schiff Bases 14
2.4 Different Bonding Modes of Schiff Bases 14
2.4.1 Monodentate 14
2.4.2 Bidentate 15
2.4.3 Tridentate 15
2.4.4 Tetradentate 16
2.4.5 Pentadentate 17
2.4.6 Hexadentate 17
References 17
3 Different Routes of Synthesis 23
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
3.1 Formation of Schiff Bases 23
3.1.1 Direct Ligand Synthesis 24
3.1.2 Template Synthesis 25
3.1.3 Rearrangement of Heterocycles (Oxazoles, Thiazoles, etc.) 26
References 26
4 Schiff Base Metal Complexes 29
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
References 34
5 Effect of Different Parameters on Schiff Base and their Metal Complex 37
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
5.1 Ionic Charge 37
5.2 Ionic Size 37
5.3 Nature of Central Metal Ions 37
5.4 Nature of the Ligand 37
5.4.1 Basic Character of the Ligand 38
5.4.2 Size and Charge of the Ligand 38
5.4.3 Concentration of Ligand 38
5.4.4 Substitution Effect 38
5.4.5 Chelating Effect 39
5.4.6 Nature of Solvent 39
5.4.7 Crystal Field Effect 39
5.4.8 Thermodynamic and Kinetic Effect 39
References 40
6 Thioether and Chiral Schiff Base 41
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
6.1 Thioether Schiff Base 41
6.2 Chiral Schiff Base 44
References 45
Part II Synthesis 53
7 General Routes of Synthesis 55
Himadri Priya Gogoi, Anmol Singh, and Pranjit Barman
7.1 Introduction 55
7.2 Mechanism of the Synthesis of Schiff Base Ligand 56
7.3 Problems Found in Conventional Method - Hydrolysis of C=NBond 59
References 59
8 Different Route of Synthesis of Schiff Base-Metal Complexes 61
Himadri Priya Gogoi, Anmol Singh, and Pranjit Barman
8.1 Introduction 61
8.2 Different Chemical Routes 61
8.2.1 Preparation of Schiff’s Bases via Aerobic Oxidative Synthesis 61
8.2.2 Synthesis of Schiff Bases via Addition of Organometallic Reagents to Cyanides 61
8.2.3 Reaction of Phenol with Nitriles to Form SB 62
8.2.4 Reaction of Metal Amides to Ketone to Form SB 63
8.2.5 Reaction of Nitroso Compounds with Active Hydrogen Compounds 63
8.2.6 Dehydrogenation of Amines 64
8.2.7 Oxidation of Metal Amines to Form SB 64
8.2.8 Reduction of Carbon-Nitrogen Compounds 65
8.2.9 Synthesis of SB from Ketals 65
8.2.10 SB Synthesis by Using Hydrazoic Acid 66
8.2.11 SB Synthesis by Using Sodium Hypochlorite 66
8.2.12 Preparation of N-metallo Imines 66
8.2.13 Preparation of N-metallo Imines (Metal = B, Al, Si, Sn) 67
8.2.13.1 Preparation of N-boryl and N-aluminum Imines 67
8.2.13.2 Preparation of N-silylimines via 67
8.2.13.3 Preparation of N-tin Imines 68
8.3 Different Methods 68
8.3.1 Classical or Conventional Method 69
8.3.2 Microwave Irradiation Method 70
8.3.3 Water as Solvent Method 71
8.3.4 Grindstone Technique 71
8.3.5 Ultrasonic Method 72
8.3.6 Green Method Using Green Catalyst 73
References 76
9 Synthesis and Mechanism of Schiff Base-Metal Complexes 79
Himadri Priya Gogoi, Anmol Singh, and Pranjit Barman
9.1 Introduction 79
9.2 Synthesis of Schiff Bases Metal Complexes 79
9.2.1 Synthesis of Ligand Followed by Complexation 79
9.2.1.1 One-Step Process or Template Synthesis 80
9.3 Synthesis of Some of the Schiff Base Metal Complexes 83
References 86
10 Synthesis and Mechanism of Chiral and Achiral Schiff Base and Their Metal Complexes 89
Himadri Priya Gogoi, Anmol Singh, and Pranjit Barman
10.1 Introduction 89
10.2 Synthesis of Chiral and Achiral SB Ligand 90
10.3 Synthesis of Chiral SB Metal Complexes 93
10.4 Chiral Schiff Bases of Titanium, Zirconium, and Vanadium 95
10.5 Chiral Schiff Bases of Main Group Metals 96
10.5.1 Manganese and Chromium Schiff Bases 97
10.5.2 Iron and Ruthenium Schiff Base Complexes 98
10.5.3 Cobalt, Nickel, Copper, and Zinc Schiff Base Complexes 98
10.5.4 Lanthanide Metal Schiff Bases 99
10.5.5 Silicon and Tin Metal Schiff Bases 99
References 102
11 Synthesis and Mechanism of Thioether: Schiff Base and Their Metal Complexes 105
Himadri Priya Gogoi, Anmol Singh, and Pranjit Barman
11.1 Introduction 105
11.2 Chemical Synthesis Procedures 106
11.2.1 Procedure for the Synthesis of Thioether-Containing Schiff Base 106
References 111
12 Computational Chemistry 113
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
12.1 Introduction 113
12.2 Application of DFT in the Field of Schiff Base and Their Metal Complexes 115
References 118
Part III Application 119
13 General Applications of Schiff Bases and Their Metal Complexes 121
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
13.1 Catalyst 121
13.2 Biological and Medicinal Importance 122
13.2.1 Antibacterial Activity 122
13.2.2 Anticancer and Anti-inflammatory Agent 122
13.2.3 Antifungal Activity 123
13.2.4 As a Drug in a Number of Diseases 123
13.3 Coatings 123
13.4 Analytical Chemistry 123
13.5 Dyes 124
13.6 Semi-conducting Materials 124
13.7 Solar System 124
13.8 Photocatalyst 125
13.9 Polymer Chemistry 125
13.10 Agrochemical Industry 125
References 125
14 Application in Pharmacological Field 129
Parnashabari Sarkar, Sourav Sutradhar, and Biswa Nath Ghosh
14.1 Introduction 129
14.2 Antimicrobial Activity 135
14.2.1 Schiff Bases Against Gram-Positive Bacteria 135
14.2.2 Schiff Bases Against Gram-Negative Bacteria 137
14.3 Antifungal Activity of Schiff Bases 138
14.4 Anticancer Activity of Schiff Bases and Their Metal Complexes 139
14.4.1 In Vitro Activity 139
14.4.2 In Vivo Activity 140
14.5 Antidyslipidemic and Antioxidant Activity 141
14.6 Anthelmintic Activity 141
14.7 Antitubercular Activity 142
14.8 Antidepressant Activity 142
14.9 Anticonvulsant Activity 142
14.10 Antioxidant Activity 142
14.11 Antiviral Activity 143
14.12 Anti-inflammatory and Analgesic Activities 143
References 143
15 Application as Catalyst 149
Saravanan Saranya and Seenuvasan Vedachalam
15.1 Introduction 149
15.2 Coupling Reaction 149
15.3 Polymerization Reaction 151
15.4 Oxidation Reaction 152
15.5 Epoxidation Reaction 153
15.6 Ring-Opening Epoxidation Reaction 154
15.7 Cyclopropanation Reaction 155
15.8 Hydrosilylation Reaction 156
15.9 Hydrogenation Reaction 157
15.10 Aldol Reaction 158
15.11 Michael Addition Reaction 159
15.12 Annulation Reaction 160
15.13 Diels-Alder Reaction 161
15.14 Click Reaction 161
15.15 Mannich Reaction 162
15.16 Ene Reaction 163
15.17 Summary 164
References 164
16 Application as Drug-Delivery System 169
Anmol Singh, Himadri Priya Gogoi, and Pranjit Barman
References 173
17 Chemosensors/Bioimaging Applications 179
K. Sekar, K. Suganya Devi, T. Dheepa, and P. Srinivasan
17.1 Introduction 179
17.1.1 Chemosensing 179
17.1.1.1 Explosives Sensing 179
17.1.1.2 Oxygen Sensing 180
17.1.1.3 High pH Sensing 180
17.1.1.4 Other Porphyrinoid-based Chemosensors and Chemodosimeters 180
17.1.1.5 Metal Sensing 180
17.2 Chemosensors 181
17.2.1 Fluorescence ON-OFF 184
17.2.1.1 Tiny Molecules Chemosensors 184
17.2.1.2 Supramolecular Chemosensors 184
17.2.1.3 QDs-based Chemosensors 184
17.2.1.4 Fluorescent Nanomaterial-based Chemosensors 185
17.2.2 OFF-ON Chemosensors 185
17.2.2.1 Rhodamine-based Sensors 185
17.2.2.2 Coumarin-based Sensors 186
17.2.2.3 BODIPY-based Sensors 186
17.2.3 Ratiometric Fluorescent Chemosensors 186
17.2.3.1 Pyrene-based Chemosensors 186
17.2.3.2 Fluorophore Hybridization Chemosensors 186
17.2.3.3 Dual-emission Fluorescent Nanoparticles 186
17.2.4 Rhodamine-based Sensors 187
17.2.4.1 Fluorescent Bioimaging of CK in HeLa cells 187
17.2.4.2 Mice Bioimaging Experiments 187
17.2.5 Fluorescent Chemosensor for AcO - Detection 189
17.2.6 CN - and Al 3+ Chemosensor for Bioimaging 191
17.3 Conclusion 192
References 192
18 Application in Industrial Field 195
M. Chakkarapani, M.A. Asha Rani, G. Saravana Ilango, and Pranjit Barman
18.1 Introduction 195
18.2 Current Status in India 198
18.3 Conclusion 199
References 200
Index 203
