Patterns of behaviour: serendipity in action for enantiomerisation of F-S-S-Cl

September 19th, 2013

Paul Schleyer sent me an email about a pattern he had spotted, between my post on F3SSF and some work he and Michael Mauksch had done 13 years ago with the intriguing title “Demonstration of Chiral Enantiomerization in a Four-Atom Molecule“.[cite]http://doi.org/d8g2nw[/cite] Let me explain the connection, but also to follow-up further on what I discovered in that post and how a new connection evolved.FSSF3-gen

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A two-publisher model for the scientific article: narrative+shared data.

September 15th, 2013

I do go on rather a lot about enabling or hyper-activating[cite]10.1039/P29950000007[/cite] data. So do others[cite]10.1038/nj7461-243a[/cite]. Why is sharing data important?

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The dimer of SF2: small is beautiful (and weird).

September 12th, 2013

Andy Extance at the Chemistry World blog has picked up on a fascinating article[cite]10.1021/jz401578h[/cite] on the dimer of SF2. This molecule has three F atoms on one S, and only one on the other; FSSF3. But all four S-F bonds are of different length. Lindquist and Dunning claim that the minimum energy pathway to dissociation to two SF2 molecules does not involve breaking either the longest or the weakest SF bond. This was too much for me to resist investigating further!

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Coarctate reactions as a third fundamental organic-mechanistic type.

September 4th, 2013

According to Herges[cite]10.1021/ci00017a011[/cite],[cite]10.1039/c2cc34026g[/cite] the mechanism of single-step (concerted) reactions can be divided into three basic types; linear (e.g. substitution, elimination etc), pericyclic (e.g. Diels Alder) and a third much rarer, and hence very often overlooked type that was named coarctate. This is based on the topology of bond redistribution patterns, an explicit real example[cite]bhsn4t[/cite] illustrating:

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Experimental evidence for “hidden intermediates”? Epoxidation of ethene by peracid.

August 25th, 2013

The concept of a “hidden intermediate” in a reaction pathway has been promoted by Dieter Cremer[cite]10.1021/ar900013p[/cite] and much invoked on this blog. When I used this term in a recent article of ours[cite]10.1021/jo401146k[/cite], a referee tried to object, saying it was not in common use in chemistry. The term clearly has an image problem. A colleague recently sent me an article to read (thanks Chris!) about isotope effects in the epoxidation of ethene[cite]10.1021/jo981652x[/cite] and there I discovered a nice example of hidden intermediates which I share with you now.

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Full-colour 3D printing of molecular models and orbitals (wavefunctions).

August 18th, 2013

We have been experimenting with full-colour 3D printing of molecular objects. I thought I might here share some of our observations. Firstly, I list the software used:

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Molecule-sized pixels.

August 11th, 2013

The ultimate reduction in size for an engineer is to a single molecule. It’s been done for a car; now it has been reported for the pixel (picture-element).[cite]10.1021/ja404256s[/cite]

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The Amsterdam Manifesto on Data Citation Principles

July 31st, 2013

The Amsterdam manifesto espouses the principles of citable open data. It is a short document, and it is worth re-stating its eight points here:

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VSEPR Theory: A closer look at chlorine trifluoride, ClF3.

July 27th, 2013

Valence shell electron pair repulsion theory is a simple way of rationalising the shapes of many compounds in which a main group element is surrounded by ligands. ClF3 is a good illustration of this theory.

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The butterfly effect in chemistry: bimodal bond angles.

July 18th, 2013

This potential example of a molecule on the edge of chaos was suggested to me by a student (thanks Stephen!), originating from an inorganic tutorial. It represents a class of Mo-complex ligated by two dithiocarbamate ligands and two aryl nitrene ligands (Ar-N:).Mo

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