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Meet Derk Haank

27 February 2015 - Scientific publishing

Meet Derk Haank. He used to run Elsevier Science, now runs Springer. Haank is a pretty important figure in scientific publishing. Springer recently acquired MacMillan. Mac Who? That is the German Von Holtzbrinck family and proud owners of the journal Nature. Who is better positioned to present a counter-view to the whole open-access debate going on (see here). Last week he gave an interview to NRC (Marcel aan de Brugh again) and as a public translation service here are the quotes.

It must be a lot easier to extort money from those poor little university librarians if you have Nature in your back pocket. Haank says it himself: "we publish anything that is scientifically OK, from barely passing to excellent", Nature on the other hand "is very selective for those articles that really make the difference in the world". According to Haank Springer hopes that 95% of the articles rejected by Nature will find a home in one of the other Springer journals. This makes sense. In his Elsevier days Haank at some point feared that "scientists would increasingly share articles and that ultimately each publication would end up with just one subscription". He takes pride in his invention of the "big deal" , the single fee for hundreds of titles. This business model, Haank explains enables libraries to handle the 7% annual increase in books and articles. This again makes sense. And what about open-access? In the open-access business model Springer would lose one third of its customer-base: those companies that do not publish. More to think about: scientists can not self-organise open-access publications. "The mutual distrust is too great".

Fluorenyl cation trapped

22 February 2015 - Organic physical chemistry

Fluorene is a typical aromatic compound and so is it's anion. The fluorenyl cation on the other hand is antiaromatic and any attempt to synthesising it would seem a futile exercise. Where some of the giants in chemistry like Olah and Schleyer tried anyway and failed some 30 years ago actual synthesis now seems in the bag although with the usual caveat that is concerns low temperature matrix isolation. Costa et al. (DOI) report that it can be made by photolysis of diazofluorene in an argon matrix in presence of a substance called amorphous ice. At 3 kelvin the first reaction product is the carbene fluorenylidene and after heating it up to 50K this carbene has reacted with water to the cation. This identification is based on IR spectroscopy and supported by theoretical calculations. The reaction of the cation with water is highly exothermic but at these sort of temperatures that reaction is at a standstill. According to Costa the cation is also stabilized because the hydroxyl counteranion is allowed to diffuse away. After further heating the ultimate product is fluorenol.

Terpenes-in-a-box

21 February 2015 - Catalysis

Zhang Tiefenbacher 2015.PNGIn an example of lab imitating nature tail-to-head terpene cyclization is found to take inside the cavity of a certain resorcinarene mimicking an enzyme (Zhang & Tiefenbacher DOI). The resorcinarene capsule is hydrophobic with a cavity of 1.4 A. The walls are aromatic allowing favourable cation-pi interactions. The cavity also act as a brønsted acid. When the terpene geraniol and capsule (10%) were combined in chloroform the main product was first linalool and finally in the course of hours eucalyptol. Six solvent molecules can fill the capsule. one substrate molecule replaces three solvent molecules. Adding tetrabutyl ammoniumbromde blocks the cavities and no cyclisation takes place. Nerol was also converted to eucalyptol. Likewise geranyl acetate was found to cyclisize to terpinene.