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Warwick.Ac.Uk/Lib-Publications A Thesis Submitted for the Degree of PhD at the University of Warwick Permanent WRAP URL: http://wrap.warwick.ac.uk/139891 Copyright and reuse: This thesis is made available online and is protected by original copyright. Please scroll down to view the document itself. Please refer to the repository record for this item for information to help you to cite it. Our policy information is available from the repository home page. For more information, please contact the WRAP Team at: [email protected] warwick.ac.uk/lib-publications 1 AN INVESTIGATION OF SOME REACTIONS OF ALUMINIUM HYDROBORATE A thesis submitted for the degree of Doctor of Philosophy by David L.S. Shaw, B.Sc. The Department of Molecular Sciences^ University of Warwick 1. CONTENTS gage Contents 1 List of Tables 6 List of Figures 7 Acknowledgements 9 Sum m ary 10 1. Introduction 11 Nomenclature 11 Units 12 Hydroborates - Historical 12 Hydroborates - Properties 13 Hydroborates - Structures 17 Hydroborates - Bonding 21 Hydroborates - Vibrational Spectroscopy 24 Hydroborates - Nuclear Magnetic Spectral Properties 27 Aluminium Hydroborate 32 Preparation 32 Synthetic Reactions using Aluminium Hydroborate - Uses 33 Aluminium Hydroborate - Structure and Bonding 34 Aluminium Hydroborate - Properties 38 Physical Properties 38 Aluminium Hydroborate - Reactions 38 Exchange Reactions and Substituted Products 40 Anionic Aluminium Hydroborate Compounds 46 Adducts of Aluminium Hydroborates 47 Vibrational Spectra of Aluminium Hydroborate 50 Nuclear Magnetic Resonance of Aluminium Hydroborates 55 Decomposition of Aluminium Hydroborate - Hydride Aluminium Hydroborates 6-1 I Contents (continued ) Page Aluminium Hydride 63 Aluminium Alkyls 64 Aluminium and Higher Hydroborate Derivatives - Octahydrotriborates - 65 Trialkyl Boranes( Alkyl Diboranes 68 2. Reaction of Aluminium Hydroborate with Alcohols and Thiols and some Compounds containing Alkoxy Groups 69 Reaction ofAluminium Hydroborate with Alcohols 72 1. With M ethanol 72 2. With larger Alcohols 74 The Reaction of Aluminium Hydroborate with Thiols 75 Preparation and attempted Preparation of Alkoxy and Hydroxy Aluminium Hydroborate Species using Exchange Reactions 76 Discussion of the Mechanism of Hydrolysis-type Reaction 78 Properties of Alkoxy and Thloalkyl Aluminium Hydro borates 80 Spectroscopic Properties 81 Nuclear Magnetic Resonance Spectra 85 3. Exchange Reactions of Aluminium Hydroborate with Trialkylboranes 88 Introduction 88 Nuclear Magnetic Resonance Properties of Aluminium Hydroborate/Triethyl borane Mixtures 89 Triethyl borane -Aluminium Hydroborate (1:1 molar ratio) 89 Triethyl borane-Aluminium Hydroborate (5:1 molar ratio) 90 Contents (continued) page Tri«thyl borane-Aluminium Hydroborate (12:1 molar ratio) 90 Triethyl borane-Aluminium Hydroborate (25:1 molar ratio) 90 Trimethyl borane-Aluminium Hydroborate (5:1 molar ratio) 90 Trimethyl borane-CimethylAluminium Hydroborate (5:1 m olar r a tio ) 92 Discussion 92 Infra-red Spectral Data on Aluminium Hydroborate Trialkyl Borane Exchange Reactions 98 Attempted Preparation of B-alkylated Aluminium Hydroborates by a Novel R eaction 102 Conclusion 102 4. Reactions of Aluminium Hydroborate with some Octahydrotriborate and Hydride Species, and their Relevance to Aluminium Hydroborate Decomposition 103 Introduction 103 Dimethyl Aluminium Octahydrotriborate 107 Further Exchange Reactions 130 5. Experimental Details 132 General Techniques 132 A nalytical T echniques 134 Spectroscopic Techniques 136 Preparation of P re c u rs o rs 136 Aluminium Hydroborate 136 Trialkyl Boranes 137 Trimethyl Porane 137 Trlethyl Borane 138 Octahydrotriborate Species: NaB^HgiC^HgO^ )g 138 Contents (continued) gage Other Precursors 140 Alanetrimethylamine 140 Dimethyl Aluminium Hydroborate 140 Tetra-ethyl Diborane 141 4-Methoxy benzyl Alcohol (Anisyl alcohol) 141 Reactions for Chapter 2: 141 Reaction of Aluminium Hydroborate with Methanol 141 Reaction of Aluminium Hydroborate with Aluminium Methoxide 142 Reaction of Aluminium Hydroborate with Aluminium Hydroxide 143 Preparation of Thiomethyl Aluminium bis (Hydro borate) 143 Preparation of Thioethyl Aluminium bis (hydroborate ) 143 Preparation of Thiobenzyl Aluminium bis (hydroborate) 144 Reaction of Aluminium Hydroborate with 2-methyl Propane-2 -thiol 144 Reaction between Aluminium Hydroborate and Tetra- hydrothiophene 145 Reaction of Aluminium Hydroborate with Cyclohexanol 145 Reaction of Aluminium Tetrahydroborate with Anisyl - alcohol (p-methoxy benzyl alcohol )t Benzhydrol (diphenyl methanol) and t-butanol (2-methyl propan-2-ol) 145 Preparation of Methoxy Aluminium bis(hydroborate ) 146 Preparation of Ethoxy Aluminium bis (hydroborate ) 146 Molecular Weight Determination of Ethoxy Aluminium bis (hydroborate ) by a Freezing Point Depression Method 146 5. Contents (continued ) page R eactions for C hapter 3: 148 G eneral 148 Reaction of Tetraethyl Dlborane with Trlethyl Alane 148 Reactions for C hapter 4 : 148 Preparation of Octahydrotr iborate Aluminium bis(hydroborate ) 148 Reaction of Dimethyl Aluminium Octahydrotr iterate with Diborane 149 Reaction of Dimethyl Aluminium Octahydrotr Iterate with Diethyl Ether 150 Reaction of Dimethyl Aluminium Octahydrotr Iterate with T rim ethyl A m ine 150 Reaction of AluminlumHydroterate with Alane Trlmethyl Amine 150 Preparation of Aluminium Hydroborate and Trlmethyl Alane E th e ra tes 150 R eferences 151 6. LI?T OF TABLES page 1.1 Elements known to form simple hydroborates 14 1.2 Physical properties of selected hydroborates 15 1. 3a 52 and Infra-red vibrations of aluminium hydroborate 1.3b 53 2.1 Selected spectral properties of RO and RS A1(BH^>2 compounds 82 3.1 Comparison of the vapour pressure of aluminium hydroborate: 96 trimethyl borane 1 :5 with trimethyl borane 3.2 Measurements of vapour pressure and hydrogen evolution 97 of an A1 (BH^) ^tBEt^ = 5:1 molar mixture 3.3a Infra-red spectral details of excl ge reactions between 99 and A1(BH )„ and BR„ 3.3b 4 '3 100 4.1 Some n.m .r. parameters for Me A1B H 110 2. 3 o page 1.1 Structure of diborane 18 Structure of aluminium hydroborate 18 1.2 Structures of beryllium hydroborate 20 1.3 Bonding in a B-H-B bridge 22 1.4 Simple view of bonding in the diborane bridge system 23 1.5 Infra-red spectrum of diborane 25 1.6 Infra-red spectrum of aluminium hydroborate 26 1.7 General rules for predicting structure types in hydro borate groups 28 1.8 Structures of aluminium hydroborate 35 1.9 M olecular energies of Al(BH4 )g 37 1.10 1H n .m .r. spectrum of AlfBH^)^ In toluene solution 56 1.11 11B n.m .r. spectrum of AlfBH^ in toluene solution 57 2.1 Infra-red spectrum of MeSAliBH^lj 83 2.2 1H n.m .r. spectrum of MeSAKBH^ 86 3.1 Typical ^B n.m .r. spectrum obtained by exchange between A1(BH4 )g and BEt^ 91 3 .2 Infra-red spectrum obtained from mixing of AlEt^ and 101 8. List of Figures (continued ) p ag e 4.1 Infra-red spectrum of Me2AlBgHg 108 4.2a 1^B n.m .r. spectra of pure liquid Me AIB.H 111 and ^ J “ 4.2b 112 11 A 4.3 Bn.m .r. spectra of Me A1B H In toluene d 114 2 o o 4.4 ^~Aln.m.r. spectra of puce Me A1B H at + 23°C 115 2 o o 4.5 Infra-red spectrum of (BH^AlBgHg 120 4.6 n.m .r. spectrum of (BH^AlB^Hg at+ 30°C 122 4.7a 11Bn.m .r. spectrum of (BH4 ^A lB ^H g a f +10° C 123 4.7b 11B n.m .r. spectrum of (BH4)2AlBgHg at -13°C 124 4.7c 11B n.m .r. spectrum of (BH ) A1B-H aX -3 3 ° C 125 4.7d ^B n.m .r .spectrum of (BH4)2AlBgHg at -50°C 126 5.1 Vacuum line 133 5. 2 Diagram of apparatus to carry out hydrolysis of 135 (BH4>2A1B3H8 5.3a Beckmann freezing point apparatus 147 5.3b Flask with n.m .r. tubeside-arm 147 'I r i d 9. ACKNOWLEDGEMENTS The research work reported in this thesis was carried out between October, 1973 and September 1976 in the Department of Molecular Sciences, University of Warwick> Coventry. I should like to express my gratitude to my supervisor, Professor M.G.H. Wallbridge, for his good-humoured encouragement and help throughout. My thanks are due to the technical staff of the Department particularly the long-suffering staff of the glassblowing workshop, Mr. P. Brindley, Mr. E. Burgess and Mr. K. Holden (now at the University of Liverpool), for building and repairing an excellent vacuum line. On a personal note, I should like to thank Mr. D .I. Atkinson for his technical assistance and friendship, and Pauline and my family for their support. Finally I must thank M rs. J.I. McKeand for patiently converting my handwriting into typescript. SUMMARY The reaction of aluminium hydroborate with alcohols and thiols is discussed, and this is extended to cover possible mechanisms for aluminium hydroborate hydrolysis. The course of the reaction was found to be dependent on the structural type of alcohol or thiol used. Substitution of a thio alkyl group for hydroborate led to preparation of the type of compound RSA1(BH^ )^ (where R = methyl, ethyl, benzyl) and properties of these compounds are discussed. Using an exchange reaction of aluminium hydroborate with alkyl borates , corresponding compounds of the type ROAl(BH^>2 (R = m ethyl, ethyl) were prepared, and their properties ascertained. The behaviour of aluminium hydroborate with triethyl and trimethyl borane is considered. This work suggests that there Is an exchange between the terminal hydrogens of the hydroborate groups and the borane alkyl groups, resulting in B-a!kylated aluminium hydroborates. B-alkylated hydroborates are also believed to be formed from a novel reaction between triethyl a lane and tetraethyl diborane. Some chemistry of the octahydrotriborate group linked to aluminium Is also discussed. Starting from dimethyl aluminium octahydrotriborate an exchange reaction with excess aluminium hydroborate yields aluminium octahydrotriborate bis hydroborate. The properties of both compounds are discussed, and the relevance of the latter to aluminium hydroborate decomposition is noted.
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