Durham E-Theses. Developing and Understanding Iridium-Catalysed Arene Borylation HARRISSON, PETER
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1 Durham E-Theses Developing and Understanding Iridium-Catalysed Arene Borylation HARRISSON, PETER How to cite: HARRISSON, PETER (2011) Developing and Understanding Iridium-Catalysed Arene Borylation, Durham theses, Durham University. Available at Durham E-Theses Online: Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: a full bibliographic reference is made to the original source a link is made to the metadata record in Durham E-Theses the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-theses.admin@dur.ac.uk Tel:
2 APPENDIX III - DFT CALCULATION DATA TABLES 1
3 1.1 2,7-disubstituted Quinolines The following methods were utilised for the optimisation and frequency calculation: Optimisation (gas phase) Frequency (gas phase) Optimisation + Frequency (solution phase) B3LYP/6-31G(g) B3LYP/ G(2df,2p) B3LYP/ G(2df,2p) scrf=(iefpcm,solvent=dmso) (tsnum=60, tsare=0.4, radii=bondi, alpha=1.20) Compound E PCM E G (gas) Δ solv G (kcal/mol)
4
5 1.2 Optimised Geometry Cartesian coordinates 1 C C C C C C H C H H C C H H N C H H H C H H H C C C C C C H C H H C C H H N C H H H C H H H C C C C C C H C H H C C H N C H H H C H H H C C C C C C C H C H H C C H N C H H H C H H H C
6 1 C C C C C C H C H C C H N C H H H C H H H H C C C C C C C H C H C C H N C H H H C H H H H C C C C C C C H C H H C C H H N C H H H Cl C C C C C C H C H H C C H H N C H H H Cl
7 1 C C C C C C H C H H C C H N C H H H Cl C C C C C C H C H H C C H N C H H H Cl C C C C C C H C H C C H N C H H H H Cl C C C C C C H C H C C H N C H H H H Cl
8 1 C C C C C C H C H H C C H H N C H H H Br C C C C C C H C H H C C H H N C H H H Br C C C C C C H C H H C C H N C H H H Br C C C C C C H C H H C C H N C H H H Br
9 1 C C C C C C H C H C C H N C H H H H Br C C C C C C H C H C C H N C H H H H Br C C C C C C H C H H C C H H N C H H H C N C C C C C C H C H H C C H H N C H H H C N
10 1 C C C C C C H C H H C C H N C H H H C N C C C C C C H C H H C C H N C H H H C N C C C C C C H C H C C H N C H H H C N H C C C C C C H C H C C H N C H H H C N H
11 1 C C C C C C H C H C C N C H H H O C H H H H H H C C C C C C H C H C C N C H H H O C H H H H H H C C C C C C H C H C C N C H H H O C H H H H H C C C C C C H C H C C N C H H H O C H H H H H
12 1 C C C C C C H C H C C N C H H H O C H H H H H C C C C C C H C H C C N C H H H O C H H H H H C C C C C C H C H H C C H H N C H H H C F F F C C C C C C H C H H C C H H N C H H H C F F F
13 1 C C C C C C H C H H C C H N C H H H C F F F C C C C C C H C H H C C H N C H H H C F F F C C C C C C H C H C C H N C H H H C H F F F C C C C C C H C H C C H N C H H H C H F F F
14 1 C C C C C C H C H H C C N C H H H Si C H H H C H H H C H H H H H C C C C C C H C H H C C N C H H H Si C H H C H H H C H H H H H
15 1 C C C C C C H C H H C C N C H H H Si C H H H C H H H C H H H H C C C C C C H C H H C C N C H H H Si C H H H C H H H C H H H H Negative frequency at associated with Si(CH 3 ) 3 rotational mode 14
16 1 C C C C C C H C H C C N C H H H Si C H H H C H H H C H H H H H C C C C C C H C H C C N C H H H Si C H H H C H H H C H H H H H Negative frequency at associated with Si(CH 3 ) 3 rotational mode 15
17 1.3 4,7-disubstituted Quinolines The following methods were utilised for the optimisation and frequency calculation: Optimisation (gas phase) Frequency (gas phase) Optimisation + Frequency (solution phase) B3LYP/6-31G(g) B3LYP/ G(2df,2p) B3LYP/ G(2df,2p) scrf=(iefpcm,solvent=dmso) (tsnum=60, tsare=0.4, radii=bondi, alpha=1.20) Frequency (gas phase) Compound E PCM E G (gas) Δ solv G (kcal/mol)
18
19 1.4 Optimised Geometry Cartesian coordinates 1 C C C C C C H C H C C N H C F F F H H C H H H C C C C C C H C H C C N H C F F F H H C H H H C C C C C C H C H C C N C F F F H H C H H H C C C C C C H C H C C N C F F F H H C H H H
20 1 C C C C C C H C H C C N H C F F F H C H H H C C C C C C H C H C C N H C F F F H C H H H C C C C C C H C H C C N H C F F F C H H H H C C C C C C H C H C C N H C F F F C H H H H
21 1 C C C C C C H C H C C N H Cl C F F F H H C C C C C C H C H C C N H Cl C F F F H H C C C C C C H C H C C N Cl C F F F H H C C C C C C H C H C C N Cl C F F F H H
22 1 C C C C C C H C H H C C N H Cl C F F F C C C C C C H C H H C C N H Cl C F F F C C C C C C H C H C C N H Cl C F F F H C C C C C C H C H C C N H Cl C F F F H
23 1 C C C C C C H C H C C N Cl Cl H H H C C C C C C H C H C C N Cl Cl H H H C C C C C C H C H C C N Cl Cl H H C C C C C C H C H C C N Cl Cl H H
24 1 C C C C C C H C H H C C N Cl H Cl C C C C C C H C H H C C N Cl H Cl C C C C C C H C H C C N Cl H Cl H C C C C C C H C H C C N Cl H Cl H
25 1.5 6-methoxyquinoline-2-carbonitrile Optimisation (gas phase) Frequency (gas phase) Optimisation + Frequency (solution phase) B3LYP/6-31G(g) B3LYP/ G(2df,2p) B3LYP/ G(2df,2p) scrf=(iefpcm,solvent=dmso) (tsnum=60, tsare=0.4, radii=bondi, alpha=1.20) Compound E PCM E G (gas) Δ solv G (kcal/mol)
26 1 C C C C C C H H C H C C H H N C O C H H H N C C C C C C H H C H C C H H N C O C H H H N C C C C C C H H C H C C N C O C H H H N H C C C C C C H H C H C C N C O C H H H N H
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