Comments

Cyclopentadiene

Nice and concise. You could have made a little more of kinetic vs thermodynamic control, perhaps putting am energy diagram in, and possibly an illustrating of the orbitals you mention. But I did appreciate your tracking down ref 3, which I was unaware of. Its nice to have the prediction actually verified by experiment.

Taxol

Your four chair isomers are spot on! Well done!! "twist-boats are always higher in energy they can be discounted" ACtually, its up to you to show that this is true. There are some conformations known where the twist boat is actually the lowest! So you do not have to make such assumptions.

You modelled hydrogenated 9 and 10; excellent! But you do not quote their energies,or estimate the heat of hydrogenation. That might have yielded some interesting results!

Spectroscopy

" Their energies were minimised using the MMFF94s force field in Avagadro then the spectra were calculated[7][8] using Gaussian". This might imply that the NMR spectra were calculated at the MMFF94s geometry? I am sure that is not what you did, but your report is unclear on this aspect. In Table 4, you do not actually quote the method used for the results. I presume you used that suggested in the script, but again unless you state it, one cannot be certain.

In your simulation, you quote the individual values for a methyl. But experimentally, these are rotationally averaged, and so you should do the same to your calculation in order to compare the two. It is quite difficult from Table 4 to see your actual assignments, since the rows do not match.

Again, Table 5 is a little tricky to analyse. Much better would be to plot the difference between calc and obs shift, as a function of each carbon, and show it as a bar chart using Excel. That way one can immediately spot outliers, and whether the distribution is statistically arranged around zero.

It is tempting to wonder whether the boat might be the actual conformation in solution? Since you calculated both using QM, you would have obtained energies (free energies?) for both. Shame you do not quote them! I found from your deposited log file -1651.464194 and -1651.459537, which makes the chair about 2.9 kcal/mol lower in free energy. So this is all stuff you could have teased out in your report.

Epoxides

Crystal structures

Excellent, you found the structures, and found lots of interesting things to say about them. Perfect!

Calculated NMR

There was no need to calculate BOTH enantiomers of the styrene epoxide. Gaussview can invert one into the other, and they would then be identical. So one calculation is perfectly OK. Table 1 (why did you restart the numbering?) again does not match rows. Thus 118.27ppm and 52.4ppm in the same row? TAble 2, average the methyls!

Calculated Rotations

"Searches for literature values of ORP were inconclusive, both positive and negative ORP values had been associated with each enantiomer, making the data unreliable. This meant it was not possible to assign the configuration of the epoxides obtained using the optical rotation data."

You could elaborate this. Thus what did Shi/Jacobsen actually report for these epoxides? One may assume that their values are reliable? You missed an opportunity here!

Table 4. Is phenylprop-1-ene not the same as trans-β-methylstyrene ? Something missing here! Again "The equilibrium constant for the conversion of the S,R to R,S epoxide was very large (8118.640311)..." is not quite the sense of what is done. The two do NOT convert. In the presence of an asymmetric catalyst, they form diastereomeric transition states which are different in energy. So your terminology is not right.

NCI and QTAIM

Nice analysis. Good!!

Suggestion

A good one!

Overall, a well thought out and thorough analysis. Excellent!!