B.R.S.M. To strive, to seek, to find and not to give a yield


And Now For Something Completely Different 4: Wikipedia Fun

Have you ever tried to look up famous chemists on Wikipedia only to end up misspelling their name or finding a more famous person who shares it?  Although sometimes this can be frustrating, it can also be pretty funny.[1] Here are a few amusing namesakes I discovered recently:


1. David McMillan

As well as being one of the leading figures in the organocatalytic revolution, according to wikipedia.org, "David McMillan is a British-Australian drug smuggler who is best known for being the only Westerner on record as having successfully escaped Bangkok's Klong Prem prison". A man of many talents. Apparently, Dave avoided recapture by his immediate acquisition of an umbrella once outside the prison walls... because escaped prisoners never carry umbrellas. Clearly a clever man.


2. Phil Baron

The real Phil Baran. Credit: Sexy Science

Although he tends to make the rest of us look bad and just won't stop writing review after review after review, I still  get excited whenever he publishes something. Apart from all that chemistry and reviewing, I have just learned from the Phil Baron wikipedia page that he's also a "voice actor, puppeteer and songwriter who voiced Piglet in the Disney Channel live-action/puppet television series Welcome to Pooh Corner". Where does he find the time?

Filed under: ANFSCD, Ask the audience, Fun | 25,548 views | 3 comments Continue reading

Selenium: Include Me Out

No, thanks.

This week I noticed that J. Derek Woollins, head of Chemistry at the University of Saint Andrews and legendary selenium chemist, recently published a review of the research leading to the discovery of his eponymous reagent in Synlett. Although, for reasons of self preservation, I tend to lose interest in the chalcogens after the first row or two, I quite like personal accounts of research so I thought I’d give it a try. Unfortunately, being an organic chemist, I couldn't follow a lot of the inorganic chemistry but I did enjoy some of the stories of things going wrong:

“Paul Kelly also later extended this work by making M–Se–N complexes using tetraselenium tetranitride (Se4N4) as the starting material. This is a very sensitive material. Indeed the first time we prepared it (from a reaction in liquid ammonia), whilst washing the red solid with a solution of potassium cyanide, nitrogen was let into the flask fairly briskly. The resulting turbulence caused an explosion, which destroyed the flask embedding pieces of red selenium into the white shirt Paul was wearing; from a distance this looked like major bleeding. Bravery was not lacking in the group during that era, and Paul Kelly also carried out what remains as the only published reaction of (extraordinarily explosive) pentasulfur hexanitride (S5N6) to give a complex containing the [S2N3]– ligand.”

Ah, wacky fun! I’m quite sure that S5N6 falls into the category of things that shouldn’t really exist, and trying to force them to do so isn’t good for anyone’s nerves.[1] Actually, the group engaged in quite a lot of this kind of lunatic chemistry. Another great example:

“Leaning on our previous work on reactions in liquid ammonia, we prepared sodium selenide (Na2Se) by the simple reduction of selenium with sodium in liquid ammonia. The resulting material is much more soluble than that prepared by the solid state route, though it is worth noting that this wonderfully finely divided solid is also very pyrophoric – on one occasion, around 75 grams caught fire in the port of our glove box with rather unpleasant consequences.

I imagine that ‘rather unpleasant’ probably doesn’t cover it. I can think of few things that would evacuate a building faster than screaming the words ‘selenium fire!’.[2] Fortunately, my own experience of selenium is a lot less exciting - I used phenylselenyl bromide a bit during my Masters to make enones, and aside from a marked decrease in affection from my girlfriend at the time, I suffered few ill effects. In fact, I suspect that beyond the old trick for forming enones (and the related Grieco olefination), many organic chemists would struggle to even think of uses for selenium in the lab. I am aware of one more reaction you can do with it, though, and I'll quickly explain why you shouldn't bother.

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A Belated Happy Birthday To KCN

Sorry this is quite late; real life and chemistry have been kicking my ass the past couple of weeks. Hopefully normal service, and more actual science, will resume shortly.

From Angew. Chem. Int. Ed., 2002, 41, 2678

The CP molecules are scary!


Without further ado, here is a roundup of my favourite colouring competition entries. In the end I didn't get that many, despite lots of people telling me this was a great idea. Most of the contributers have already posted their entries on their own blogs, so if you keep up with other chemistry blogs (and you should, because there are some that are much better than this one) you've probably seen these already. So, in chronological order:

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A New Coupling Agent, And Sandmeyer’s Other Reaction

I wrote this post a couple of weeks back, but wasn't happy with how rambling it was. Anyway, it's only getting more out of date, so I'm putting it up now. Someone might learn something.


I’ve always had a soft spot for hypervalent iodine reagents, especially iodine(III). In fact, they were the cornerstone of a methodology project that I worked on last year. You can imagine, then, that the rather usual looking iodosobenzene derivative above, which was published in Org. Lett. a couple of weeks back (DOI: 10.1021/ol301085v), immediately caught my eye. Such compounds tend to be very useful oxidants, and you can check out a few recent applications on the relevant organic-chemistry.com page. Surprisingly, though, this wonderful new reagent wasn’t being touted as an oxidant (although I’m sure it is)… apparently, it’s a great new coupling agent!

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A Birthday Surprise for K. C. Nicolaou

Update 1930, 20-06-12: Just noticed a mistake in my haplophytine structure (cdx, png and jpg) - a mesyl group where there should be an OH. If you've already downloaded/printed this please get the new, corrected version before continuing. Sorry!

Also, check out the first entry, from DrFreddy over at Synthetic Remarks!

Before you hurry to  check JACS, I made this myself. The image, that is.

The ongoing trend towards more colourful graphical abstracts is a perennial topic for discussion around the blogosphere.[1] Rather than draw attention to recent crimes against chemical decency, many of which can be found at TOCROFL, I am today proposing something new.[2] As many will know, the current spate of increasingly lurid abstracts can be traced to one man, American Cypriot and legendary synthetic chemist K. C. Nicolaou. But when did it all start? The cover of Classics in Total Synthesis I, published in 1996, appears to be free of such visual pollution, but it seems that by 2003 when Classics II and his autobiographical Tetrahedron prize essay were published that the inveterate colouring in had begun, and his papers are now rarely seen without it. However, I'm not going to join the online castigation of this questionable new form of art. Far from it. In fact, as it's KCN's birthday in a little over two weeks from today, I propose the WORLD'S FIRST CHEMICAL ABSTRACT COLOURING COMPETITION!

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Chemical Etymology 1: Introduction

Credit: xkcd (http://xkcd.com/1012/)


I still find myself encountering unfamiliar terms in the literature all the time. Sometimes in my favourite organic chemistry journals, but especially when I stray further away from ‘pure organic’ into biochemistry, pharmacology, physical organic chemistry and other areas I know much less about. Before (or after) resorting to looking up new words, I really enjoy taking a guess at what they mean based on the smattering of Latin and Ancient Greek I learned at school and picked up over the last few years as a scientist. Strangely, I also find that knowing where words come from really helps me remember them, and I’m much more likely to know what they mean when I see them again. I’m not a linguist, but it seems to me that actually just a few root words seem to crop up rather a lot, and I’ve found that being familiar with a handful can be pretty useful. The aim of this post, and probably a couple more over the next month is to try and teach people who have never considered the origins of chemical terms something new.

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Conditions You’ll Probably Never be Desperate Enough to Try

Or: Somewhat Like Cooking

We all know what it’s like to be desperate for a reaction to work; to need a result so badly, or to have a supervisor breathing down our necks, telling us that something must be possible. I’m sure all bench chemists can remember searching the literature for a procedure to prepare a given compound, only to find one, read it and then discard it for being too dangerous or just plain ridiculous. We can all probably think of a few procedures that we're just not paid enough to follow. For example, before Christmas I wanted to make some of this carboxylic acid.

Easy, right? Surely you just oxidise the 2,5-hexadienol that you can get in one step from allyl bromide, unprotected propargyl alcohol and indium? Nope, there are numerous preparations reported, and they all use either tin, or worse, nickel tetracarbonyl. A thing that myself and Derek Lowe definitely won’t work with.[1]

Yup, chemists love to talk about dangerous procedures. But what about ridiculous ones? I once heard an academic tell a story about his time as postdoc with Steve Ley. In his first few months in the group, another postdoc whom he referred to as ‘Crazy Norman’ had been working out the last few steps in a natural product synthesis. The final reaction was the selective reduction of one of three or four double bonds in the molecule by hydrogenation. Norman performed this reaction once on a small scale, got some NMRs and then left and moved on. After he was gone, Ley set another postdoc the task of making a little bit more of the natural product, by repeating Norman’s final step. But they couldn’t. The particular selectivity that Norman observed (and had the NMR data to prove) was never seen again. His successor tried everything – different catalysts, solvents and temperatures. New glassware, clean stirrer bars, old glassware and dirty stirrer bars. They stirred clockwise and anticlockwise, by the window and in the dark. It was rumoured that someone in the lab might have been doing some sulfur chemistry on the day when Norman did his reduction, so they tried even tried wafting some thiols at the flask full of catalyst and solvent, to maybe poison it just a little bit. Eventually, they rang up Norman to ask if he remembered doing anything – anything at all – unusual when he ran the reaction. He thought for a while and then replied, in total seriousness, “I think I might have washed the glassware with Vimto”.[2]

Image from americansweets.co.uk

Give that man a Tet. Lett.! Here are a few other examples of ridiculous things you’ll never try:

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A Little Self Deprecation in Tetrahedron

This caught my eye while reading Tetrahedron this morning. At first I thought it was a mistake, but then I realised that it was also in the PDF as well, presumably okayed by the authors. I think it's pretty funny to see this title in the TOC with 'Orginal Research Article' next to it:

Strangely, the rest of the paper seems quite confident. I guess time will tell.

Filed under: Ask the audience, Current Literature, Fun | 31,301 views | 3 comments 3 Comments

And Now For Something Completely Different 3: Some Tips On Style

Heres a little something I wrote on the flight back from the conference I attended before Christmas. It didn't quite turn out right, which is why you haven't seen it yet, but I'm a bit busy and uninspired right now so I've dredged it out for your enjoyment.

Answer: All of them, obviously

As anyone who has ever read a paper will know, scientific English is a bit different from the stuff we speak around the coffee table (and what you’ll read here). Basically, the aim of academic writing is to sound as intelligent as you can while still being quite vague. Language should be as grandiloquent as possible, to the point of obfuscation, and common words must never be used when more bookish ones are available. There are several classic papers which I needed a copy of the Oxford English Dictionary to decode. And I’m fine with that; that’s how it should be.[1]

Unfortunately, in recent years, the primary literature has become increasingly accessible and easy to read. It all began with the advent of Chemdraw, robbing the world of the beauty of stencilled/hand drawn structures, and the unabated simplification of the language still proceeds apace. This must stop. It is not acceptable to write that reactions ‘give’ or ‘yield’ particular compounds. Words like ‘furnish’, ‘afford’ or even ‘educe’ are far superior, and one should try to use a different one in each instance. Here are a few further ways to decrease the readability of your work and frustrate and confuse native and non-native English speakers alike. Just remember, you’re really doing them a favour.[2]

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Guess That Venue!

While sorting through the photos from last fortnight's conference/holiday I found this beautiful shot of the lecture theatre complex in which I gave my talk. It's not quite finished... but where is it? Answers on a postcard!

P.s. This is not a joke. I seriously attended a 4 day conference here. I like the yellow curtains on the right, leading up to the entrance. The phrase 'lipstick on a pig' springs to mind.

Filed under: Ask the audience, Fun | 28,693 views | 4 comments 4 Comments