A group down the hall recently cleaned out their lab space and a number of free books appeared in the hallway. I quickly snatched up a book published in 1978 entitled "Guide for the Perplexed Organic Experimentalist." My admiration of chemists of the past has grown over the years. It is easy to take for granted the NMR located 30 feet from my desk or the instrument facility downstairs to which I can submit a sample for MS and receive a spectra back in less than a day. Not to mention the wonders of my computer, which I can use to quickly draw chemical structures, predict NMR shifts, process/print/and store NMR spectra, render accurate 3D models of my molecule, determine if a substrate that has never been synthesized in a lab will (theoretically) fit in the binding pocket of a protein, search published chemistry literature for a specific reaction (as long as no one else is trying to do the same), type and revise manuscript or report drafts, and email coworkers or colleagues and potentially receive speedy replies to my inquiries. The list goes on…
Over the past month, I have been reading Loewenthal’s guide, noting his particularly witty or outdated remarks for this weblog entry. I’m not writing to pick fun at the old ways of chemistry, but rather to spread my appreciation of modern practices. All quotes are taken from Loewenthal, H.J.E. Guide for the Perplexed Organic Experimentalist, 1978, 1-174. My commentary is in italics. Loewenthal’s in bold. Enjoy.
Refrigerators and Cold Rooms. These may malfunction, and catch fire or explode, at any time. Really? Good thing my hood is 2′ away from our freezer.
At least once a day while in the laboratory stop and ask yourself what you would do should an accident or fire occur at that moment: …Where is the nearest sand bucket? Does it contain sand or cigarette butts? Just checked. Our sand bucket contains neither sand nor cigarette butts.
When the components [of a prep-TLC plate] are coloured in the visible region one is often tempted to preserve the plate for posterity as the dernier cri in post-impressionist painting (anyone wanting to go in for his seriously is advised to use crude products from an oxidation with dichlorodicyanoquinone). Our million dollar idea, Jeff? I think Carbon Art LLC needs to sell mine.
In many institutions the demand for cleaning tissue reaches alarming dimensions at which point it becomes clear that it is being used for purposes best described as non-scientific. I now suggest a reasonable and far more economic alternative: toilet paper. In principle, it is exactly the same. You will soon get over the psychological block; and if the secretarial staff do not, so much the better. Non-scientific? But Bob told us not to pick our noses in lab.
…that part of any library which houses [Beilstein’s Handbuch] is the most frequented one and that area should be reserved for Chemical Abstracts readers only. It should also go without saying that no volume of this work should ever leave that area and that its binding should receive special care. I love interlibrary loan. I haven’t been to the library in search of scientific literature in months.
There was a time when the abstract would refer directly to all new compounds made, their melting or boiling points and possibly other physical properties, and outline details of their preparation. And at that time the actual papers were just as boring as the abstracts.
[When writing to the author of a publication], do not forget to check whether there has not been a change in address from that given in the article, lest you commit the unpardonable offence<sic> of not knowing that the man has moved to a more prestigious institution. I hope his email address hasn’t changed.
On organizing your information: ‘Having it at your fingertips’ is a figure of speech commonly used. You can turn it into reality only in the form of a Card Index. There should be a card for every topic, and there should be cross-referencing cards pointing in all feasible directions. You should always have a supply of cards with you; envelopes or paper napkins get lost, mixed up or used for other purposes. There is no need to use the customary stiff cards; slips of ordinary paper cut to appropriate size will do just as well…Your Card Index is an extension of your memory cells and as such should remain strictly your private domain. As your stack accumulates your popularity as a source of information with your co-workers will grow, but-never ever lend out cards to anyone else. Am I screwed if my computer password is written on a napkin?
It is safe to assume that any author who has taken care that his work is reliable and reproducible will have taken equal pride in describing the work accurately, clearly and unambiguously. For example, the word ‘treat’ (’the solution was treated with…’) is frequently a convenient term to use when the author has forgotten exactly how it was done. Wait, I’ve used the word ‘treated’ before…
It has been reported that placing a sheet of aluminum between the stirring motor and reaction flask improves evenness of stirring… I love my IKA stirrer/hot plate combo. And I don’t even have to use foil to make it work.
Above all, their [a Dewar’s] protective metal enclosure makes magnetic stirring well-nigh impossible. Did I mention that I love my IKA? I don’t have to use foil AND it can stir through a Dewar.
Wooden boiling sticks (applicators) are quite out and should be thrown away or put to some quite different use. If applicators have been ‘out’ since 1978, why the hell are my students still required to use them when boiling a solution?
In many laboratories [ensuring an inert reaction atmosphere] is tackled by an array of often colorful and sometimes grotesquely (not to say downright Rabelaisian) shaped rubber balloons at strategic positions. This looks cheerful on slides, but one soon finds out that this approach has severe limitations. My balloons are quite festive. They look cheerful in person, too. I have yet to discover any limitations worthy of the ’severe’ descriptor.
On rubber septa and syringes: Some people swear by their use. Many others swear while using them. Only the most expensive types of septa are made of an elastomer which is resistant both to chemical attack and to the results of repeated puncturing. Also it is difficult to find septa in a sufficient range of sizes to fit various openings or even just to fit all standard joint openings in common use. A quick walk down to the stockroom and I can outfit my hood with appropriate sized septa for all of my glassware, resistant to chemical attack AND repeated puncture. I both swear by their use and swear while using them, but then again, I tend to swear a lot.
Dropwise addition from a syringe, except when using an expensive and space-consuming device, can never be as simple and accurate as from a burette. In my opinion the use of a syringe can be justified only where volumes of less than 0.05 ml are involved. Just did a dropwise addition from a 10 mL syringe yesterday. It was simple enough.
[Removal of grease from joints] is best done by wiping them several times with a tissue paper lightly soaked in a solvent such as carbon tetrachloride. Carbon tetrachloride is scary shit. Stick to hexanes.
On packing a column: In all cases the column should be perfectly vertical and should be vibrated by hand or with an electrical vibrator until the adsorbent has completely settled. You keep a vibrator in the lab?
On TLC: How did we ever manage without it? On the question of whether to make your own plates or to invest in the commercially available ones it is hard to give any definite advice. How did we ever manage without commercially available TLC plates?
[Spotting TLCs] should always be done as uniformly as possible and reliance on home-made capillaries is not recommended. Hey, my capillaries are home-made. I’m damn proud of them too.
There is no sense recording [Rf values] unless with reference to a standard substance run on the same plate and at the same time [under the same atmospheric conditions]. Unless you are working in a laboratory which has automatic air conditioning these are entirely beyond your control. I have air conditioning and I still see no sense in recording an Rf value.
It was said of Adolf von Baeyer that his success [in recrystallization] was in large measure due to his large beard harbouring seeds of every compound ever made. However, even if beards are in fashion again this alone is not a good enough reason for following his example. Some people believe in mascots or singing operatic arias; at least it cannot do any harm. I need a mascot for my recrystallizations. Suggestions?
Should you come across an ancient sewing machine, of the foot-operated type, requisition it. The treadle, when connected to an electric motor, is a very suitable support for items to be shaken, and the open lattice work usually encountered makes firm attachment by springs or rubber bands an easy matter. Talk about space-consuming. Geesh. Just use the sonicator. It doesn’t require the use of springs and rubber bands to work.
A good tool for cutting [small filter paper circles] out of larger sizes is a very sharp and scrupulously clean cork borer with the appropriate diameter. I wonder if the stockroom sells cork borers. Wait, they sell every size of filter paper I could ever conceive using.
That’s all for now. I doubt Loewenthal realized that he was writing a comedy for the 21st century. Let it be known that I love my IKA stirrer, teflon stir bars, rubber septa, commercial TLC plates, argon balloons, the stockroom, and my computer. In all fairness, I should also note that this book contained good suggestions that are still relavent to the modern perplexed organic experimentalist. Not THAT much has changed. This book is available for checkout on my desk…just don’t steal my giant stack of notecards.
