Tuesday, 26 February 2013

Inspirational Women: Chemistry Edition

Every field of study has its neglected and maligned women. Rosalind Franklin is archetypal: her work led directly to the discovery of the structure of DNA, but she was subjected to institutional and personal sexism, and generally ignored by history. Dorothy Hodgkin was dismissed as an "Oxford housewife" by the Daily Mail upon receipt of the 1964 Nobel Prize for her groundbreaking work on protein crystallography. And how many biochemistry students know that Menten, of Michaelis-Menten fame, was named Maud?

What about organic chemistry? Our field very easily falls prey to the "Great Men" scheme of history. Our history is one of male names. Think of landmark experiments: Wรถhler's synthesis of urea; Robinson's biomimetic synthesis of tropinone; Miller's prebiotic synthesis of amino acids; Woodward's synthesis of... well, everything!

Even when we're not thinking of history, our language is. You could probably construct an alphabet of reactions named after men - from (Rolf) Appel to (Theodor) Zincke, via Roberts Bergman, Grubbs, and Shapiro. Even the Julia reaction is named for a man. The few exceptions that are named for women simply prove the rule. In the immortal words of Flo Rida, where dem girls at? (with apologies)

And so, we humbly present five inspiring women of chemistry. I've picked scientists who are either retired or deceased, whose work is important, and who have overcome the odds to succeed. Think I've unjustly overlooked your hero? Leave a comment and let me know!

Gertrude Elion (1918-1999)
A legend of drug discovery, the importance of Elion’s work is self-evident. Her syntheses of purines and study of their biochemistry led to a number of firsts – including the first chemotherapy for leukaemia, the first immunosuppressant, and the first drug for herpes.  She received a share in the 1988 Nobel Prize for Physiology or Medicine, a number of honorary degrees, and senior positions in a list of organisations as long as your arm. Siddhartha Mukherjee describes her as “one of the most innovative synthetic chemists of her generation”. This extraordinary person overcame immense barriers to succeed.

Anyone seeking inspiration should read her autobiography on the Nobel site. An immigrant to the US, she was moved to study chemistry by her grandfather’s death from stomach cancer. As a grad student she held down a full-time teaching job while carrying out research at night and on weekends for two years. She earned an M.Sc., but abandoned her Ph.D. after several years in order to maintain her job. In her own words, “Years later, when I received three honorary doctorate degrees from George Washington University, Brown University and the University of Michigan, I decided that perhaps that decision had been the right one after all.”

Darshan Ranganathan (1941-2001)
The field of supramolecular chemistry would barely be the same without her pioneering work. She drew inspiration from nature to create chemical models of metabolism such as the urea cycle, and supramolecular assemblies of peptides capable of mimicking biological function. Her creations acted as synthetic ion channels and receptors, offering insight into the mechanisms of life. In addition to research, she was a great communicator of science, and regularly published Current Highlights in Organic Chemistry.

Despite her brilliance and an outstanding record, including a stint as a post-doc in Derek Barton’s lab, she was constantly held back by systematic sexism. She spent a long period of her career being consistently refused an academic position in her university on the grounds of gender, and because her husband also worked in the department. Late in life, she finally began to receive some of the recognition she had so thoroughly earned.

Irina Beletskaya (1933-)
Methodologist extraordinaire! Her work on novel metal catalysis, including the use of lanthanides, nickel, and palladium, foreshadowed the modern boom in this field. Similarly, she pioneered metal catalysis in aqueous dispersions and solutions – a central tenet of ‘green chemistry’. As well as contributing to the development of reactions which are at the heart of modern synthesis, she studied mechanism in depth. The importance of her studies of electrophilic substitution has been compared to that of Ingold on nucleophilic substitution. 

Much of her later work was accomplished in the turbulent period around the collapse of the Soviet Union, including massive cuts to the science budget. She is currently the head of the Laboratory of Organoelemental Compounds at Moscow State University, a post she has held since 1989.

Asima Chatterjee (1917-2006)
An archetypal organic chemist: her interests were about as close to pure synthesis as is possible. Her research focused on natural product synthesis, from glycosides to coumarins and beyond, most notably on indole alkaloids. Beyond her contributions to the art of pure synthesis, her work led to the development of antiepileptic and antimalarial drugs.

The barriers Asima Chatterjee surmounted, and precedents she set, are truly remarkable. She was the first woman to receive a D.Sc. from an Indian university, the first woman to hold a scientific chair at an Indian university, and the first female scientist to be elected General President of the Indian Science Congress Association. Her early career was plagued by an almost complete lack of funding for essentials of research: scholarships for students were rare, and invariably supplemented by other work; spectra were outsourced abroad at presumably great expense; materials and equipment were routinely borrowed from better-funded neighbours. This account from a former student is worth reading.

Clara Immerwahr (1870-1915)
Most famous as the wife of Fritz Haber, this remarkable woman was a brilliant chemist in her own right. She was the first woman to earn a Ph.D. in chemistry from a German university. Her career was cut short by her marriage and the commitments it entailed to running a household and raising a family. Undeterred, she became her husband’s assistant and translator, a latter-day Madame Lavoisier. Her quiet efforts earned her a dedication in his seminal textbook on thermodynamics. A very thorough and readable biography is available at the Jewish Women's Archive.

Driven by his patriotism, and perhaps a need to overcome the prejudiced his faced for his Jewish ancestry, Haber pioneered the weaponisation of chemistry on behalf of Germany. Clara openly opposed his work, describing it as a “perversion” of science. She was publicly denounced by him and the nation for her "treasonous" attitude. Ultimately, following the first deployment of chlorine gas at Ypres, she committed suicide with her husband’s pistol. Her motives are unknown.

While she may not have been a synthetic organic chemist, her moral stand against her husband’s wartime research is a lesson to us all.

This post draws heavily upon material from the wonderful Encyclopaedia of World Scientists by Elizabeth H. Oakes, the Chemical Heritage Foundation, and the Jewish Women's Archive. Other sources include the Nobel Foundation, humantouchofchemistry.com, and The Emperor of All Maladies by Siddhartha Mukherjee (which, incidentally, is a tour de force and I strongly recommend).

Sunday, 24 February 2013

Not Quite Science: tackling academic fraud

This morning, I woke up, stumbled blindly across my room in search of caffeine, and checked the notifications on my tablet. Yet again – an irritating email from Lashzone, this time cunningly disguised under the totally different name of 'Lashxone'. Not heard of them? This company is one of those professional academic cheating services. You send them your assignment brief, they’ll write it for you for a fee. The new branch Lashxone goes one step further and provides answers to your exams, suggesting that you check your email in a mid-test bathroom break. Not much different maybe than what’s gone before perhaps (I really wouldn't know) – except for strongly aggressive marketing and the lack of "this is for informational purposes only" – they’re blatant and unapologetic about their desire to deceive. 

Academic fraud like this is surely one of the biggest potential dangers to modern science. The thought of someone getting the same degree as I’m working towards without any of the slog and work I’m putting in is a galling concept. Worse, if you extend the principle to later stages of science education with research fraud, wasting thousands of pounds of grant money and everyone’s time by publishing false results is a direct attack on scientific progress.  

However for Lashzone, there is a curious backstory that a quick Google of similar sites (ugh, with a side-helping of ugh) doesn't show. Whoever made this company is as angry as we are about them. Visiting their website armed to the teeth with virus filters, the first thing I note is an image of two king cobras with the caption "if you recognize some of your teachers in this photo, you will need our help". Lecturers and tutors are snubbed as "some 'doctor' that can’t tell his left hand from right", ranting "I know it’s your job to bluff about everything, especially about the amount of knowledge you have, but people are not as dumb as you think".

We have all had experiences with a slightly abusive professor in our time. But thinking about my tutors and the faculty at my department, it makes me annoyed at best to hear them described in this way. Does this author think their anger resonates with a lot of students? And more importantly, does it actually resonate? I'm no psychologist, but it seems as though the author of the Lashzone emails and blog has some deep issues with professors. Can one person's hurt spiral and cause a snowstorm? 

Well, no. Although they claim to have 7,000 customers across "the three continents" (someone should let them know there are more than three), the most public interest they seem to have received is an article and fake assignment request from an Oxford University student newspaper.

The "them and us" atmosphere Lashzone is trying to cultivate just doesn't exist with students, at least not in my experience. The pretence that all of their critics are professors is ludicrous, particularly when aimed at a newspaper whose title is "the Oxford Student". There probably are undergrads everywhere who won't bat an eyelid at undermining all their peers and their own field just to get a top class degree, but thousands of students didn't come together and march because we're annoyed that our tutor didn't give us the extra 1% we felt we deserved - the ones we are angry at are politicians doing exactly the same thing as Lashzone is: devaluing the degrees we're working day and night for.

More critically to their reputation even amongst unscrupulous students, I honestly wouldn't touch their work with a bargepole, even if I did become an evil undergraduate determined to screw over my peers overnight. Badly-written emails and slight twisting of their critics' words prove them untrustworthy even as fraudsters. Lashzone staff are certified to have a Bachelor's or Master's degree in the relevant subject - oh, so not much better qualified than their customers! A useless disclaimer promises your money back if you get below a C. If you're that desperate that you will pay money to a criminal (they seem to have used a phishing scam to get students' email addresses for advertizing) to get a grade - you're going to want more than a C for it. Not to mention that any decent tutor will notice immediately when a student's work is out of character, particularly in the case of arts students, who are also catered for.

Lashzone rating: 0/10.

This week, I have been mostly reading...

It's been a few days since #chemclub kicked off on Twitter, so I thought I'd round up a few highlights ahead of the week to come. If you're not sure what I'm on about, have a gander here.

Wednesday, 20 February 2013

The first rule of #chemclub is...

Here's an idea:

I subscribe to something like 20 chemistry journals' ASAP feed, and unless it's directly relevant to my work, it's easy to miss really cool, interesting new work. In fact, half the time I pick up on great papers from Twitter. 

We chemists are lucky to have a critical mass of social media addicts with an eye for good science. Why not harness this precious resource?

If you read a paper worth talking about, tweet a link and quick summary with the hashtag #chemclub.

Keep an eye on the #chemclub hashtag to find interesting papers (for pleasure... or literature presentations) and hopefully discussion. The idea is not to have a formal, regular discussion between a set group of people, but to quickly highlight cool papers and discuss them with whoever happens to be around.

Other possibilities would be classic papers, weird or unexpected results, or comedy gold.

@pnowak87 has already kicked off with some #BlogSyn fodder:

I'll do a weekly round-up of the best and post it up here for your delectation.

Wednesday, 13 February 2013

Crafty chemistry

Twitter user @andyextance posted this quote earlier*:
'Biologists are better scientists than chemists, they form hypotheses' Dovichi
This is something I wonder about on and off: how does the average synthetic chemist fit into the idealised "scientific method" of hypothesis generation and testing?

Day to day, it often feels that organic chemistry is more like an art than a science. Reactions are often perfected by brute force - keep doing it, tweaking conditions, until it works! It's often not clear why a given set of conditions work on one compound but not another. This is not to say that there aren't good reasons, just that they may be subtle and difficult to predict or explain without careful study. In this way, we're perhaps more like craftsmen than scientists.

On the other hand, every reaction performed, every little alteration to the conditions, tests a hypothesis (or ought to). For example, one of the first papers out of the lab I work in uses a copious dose of TMS-Cl to help along a 1,4-conjugate addition. The addition of TMS-Cl was not arbitrary: it's a Lewis acid, and adding it tested the hypothesis that it would activate the enone to reaction.

Our hypotheses may often be less grand a little more off-the-cuff than those of a biologist, but I don't think it makes us inferior scientists - just messier.

*earlier = about five minutes ago; I am killing time while a Reaxys search completes! 

Saturday, 9 February 2013


I saw a fun video on Boing Boing recently:

The video shows a product called "Ultra Ever Dry", which is apparently an "amazing new nano polymer". It seems to repel pretty much everything with impressive resilience; I gather you're meant to spray it onto things you don't want to rust, or maybe just your boots when you go hiking. Maybe it'd be good for my lab coat...

The website makes some impressive claims:
Dust, dirt, water and other liquids that contain bacteria or radiation never actually contact the surface of the coated material so bacteria and radiation is greatly diminished or eliminated and easy to decontaminate to sterile, if needed.
I'm sure the nuclear industry would be interested to try it!

I was intrigued, so decided to try to find out what it's actually made of. Spoiler: I didn't succeed. My first thought was a perfluorinated polymer - mainly because it sounds snappy, but also because perfluoroalkanes will pretty much repel god. Molecules with many carbon-fluorine bonds have very weak interactions between molecules, and a dense shield of electrons around them, which prevents them from forming strong interactions with solvents and the like.

Which leads to this:
Reprinted with permission from Zhang, Chem. Rev. 2004, 104, 2531. Copyright 2004 American Chemical Society.

What you're looking at is a mixture of water, an organic solvent, and a perfluoroalkane (each with an appropriately -philic dye). Handy lab technique, that one. Also useful in the kitchen; Teflon is a perfluorinated polymer (h/t @V_Saggiomo)

So, what's Ultra Ever Dry made of? They tell us that it's a "nano polymer", by which I understand "polymer we want to market". I spent a whole five minutes scouring the information on their site for clues. There's some useful info on the chemical composition. For a start, apparently it has a "fragrant mint-like odour" and is biodegradable. Application is a two-step procedure, involving two solutions. Otherwise, we learn that it doesn't immediately repel ethanol or skin oils, and is resistant to extremes of pH.

More importantly, we find that the base coat consists of a bunch of reasonably volatile solvents and the magic polymer and additive. The top coat, interestingly, consists of silica and a magic additive in acetone. It may be that my aversion to the word 'nano' is premature; a lot of work on hydrophobic surfaces seeks to create a surface like a Lotus flower, which has a well-defined structure on the nano-scale, often composed of silica. It's this structure, rather than the properties of silica itself, which leads to hydrophobicity.

What surprises me is that, as far as I know, this usually requires special coating procedures. For Ultra Ever Dry, you simply spray on the bottom coat and let it set, then repeat with the top coat. No heating necessary.

Presumably, therefore, the bottom coat acts as an adhesive and provides structure, while the top coat provides the hydro- and oleophobic property. I'm not really sure how you'd get the right kind of structure to achieve this with such a simply application method, so I'm quite impressed.

So how does this work? Leave your wild speculation (or learned opinion) in the comments...