Yung JOC
October 21st, 2009 by excimer
My overuse of pop culture references is intended, in part, to alienate our older readers. Old people smell funny and complain a lot.[1]
Anyway. I have a communication in press in the revered Journal of Organic Chemistry.[2] Now, I like JOC. They have the strictest guidelines for compound characterization of any chemistry journal, which I think all journals should emulate. They’re so dead-set on it that the editor-in-chief of JOC, Dale Poulter, complained about when people don’t provide the requested supplemental information, even when it happens only a fraction of the time! That’s dedication right there. Sticking to your guns. I like it.
When I was compiling the SI for my paper, I went through the JOC Author Guide just to make sure I was following all the rules, lest I mess something up and Dale’s soldiers come to my house and throw me a blanket party. I expected the guidelines to be similar to JOC’s younger (and sexier?) sister journal, Organic Letters. And they are, to a point. Except for one little distinction which caught my eye:
“Sources of reactants, reagents, and solvents available from major laboratory chemical and biochemical supply firms should not be identified except in the case of starting compounds that are unusual or not widely available, or when the author has evidence that the use of material from a particular source is critical to the outcome of an experiment… Manufacturers and model names or numbers of spectrometers, chromatographs, polarimeters, and other standard laboratory instruments should not be identified. Commercial and institutional providers of analytical services (or locations of instrument facilities) should not be named.”
To my knowledge, no ACS journal has this distinction aside from JOC. Org. Lett. doesn’t. JACS doesn’t. I find it to be rather arbitrary and contrary to a policy of full disclosure. I would think that you’d WANT to know where they got their chemicals from.
[1] As do many grad students.
[2] To hit RSS feeds soon now! It’s nothing groundbreaking, but it’s cute.
congrats on the article!
i agree that it’s arbitrary, but i can kind of see their point. well, the lazy part of me who dislikes writing and reading exceedingly long experimental sections.
there are the cases where reagent purity has played a crucial role (eg, the brouhaha over Fe catalysis lately), though.
…not to mention this article.
not to mention this article
http://www.unodc.org/pdf/research/Bulletin07/bulletin_on_narcotics_2007_Zerell.pdf
Damn Milkshake, that’s quite a find!
I wonder if the Colombians will try to one up them!
One can never learn everything about scale-up techniques and telescoped procedures… By the way, I just had a and nice conversation with a at Aldrich “Screening Department” after ordering 100g of Na2HPO2 hydrate that is on the gov watch list of precursors (which they did not tell me beforehand when I ordered the stuff) and which then held up the order for several days and they did not feel like actually processing it, and you know, like letting me know about it, it because they “had a back-log” and I had to actually call them up to find out why nothing was coming. I was angry as a bee.
suckers. little do they know, there’s not only a batch of meth on the way… but enantiopure meth.
weird. i always kinda thought that research labs essentially had carte blanche with regard to “watched” chemicals…
and, given that you were indeed shipping stuff to a legit lab, how’d that customer service call go?…
I guess established organizations get less hassle when buying ether, acetone, toluene (these common solvents are on the list as well); the chemical supply companies would have to go nuts otherwise. Methylamine is flagged for “larger-than-small” quantities of concentrated aqueous solution (but you could buy half liter of 33% ethanolic MeNH2 without a papework) . Acetanhydride is also on the list, so is piperidine and benzyl chloride – its getting quite ridiculous, and the worst part is that you cannot always predict what will trigger the verification process and hold up the order. I guess the listed “precursor” reagents that are not used as widely, say hypophosphites, gets full baloney – even if you are buying the “unnatural” enantiomer of norephedrine that you cannot use to make illegal stuff. Chloral hydrate, a commodity reagent useful for making isatins is even more hassle to get because it is class IV since it used to be used as a sleep med like a century ago so it got thrown into the same group like barbiturates…
Optically pure meth is actually the most commonly sold product because the best starting materials, ephedrine and pseudoE, are available optically pure, their hydroxy-keto precursors being made by fermentation of benzaldehyde.
yeah. from what I gather, the watched chemical list is just a major pain in the ass to anyone who’s not ordering gallons of stuff to their garage in Iowa….
Most of those chemicals look like they have plenty of other legit uses aside from illicit drug manufacture, and any ambitious degenerate can easily lookup drug syntheses from non-watched chemicals.
but, yeah. ya got me there. If you had Na2HPO2, you’d most likely be reducing ephedrine… if you want to go about it the not fun way. But I’m a chemist, not a drug lord, so I’d prefer a more synthesis based approach, thankyouverymuch.
Well, cute is what we aim for. Congrats! I almost fell off my chair when I saw the Yung Joc picture. Good one.
Damn, strange!
If you must disclose your hardware then you must also disclose your wetware,
http://infoproc.blogspot.com/2009/10/affirmative-action-numbers.html
Congrats on the paper. Did you make a good use of both of the most versatile lab instruments? http://pubs.acs.org/doi/full/10.1021/jo900641t
“uhuhuh I got a JOC paper uhuhuhuhuhuh look at me”
Speaking of regulated chemicals: this shit gets way more ridiculous in Russia. People have come with all kinds of workarounds. Sometimes it’s as simple as ordering “ethoxyethane”.
Someone had huge troubles ordering deuterated solvents. The word “isotopes” in Cambridge Isotope Labs caused a major stir in little brains of the morons who processed the order.
wow… I thought I have problem ordering acetic anhydride (with police permit, declaration letter, forms to fill) on my side, because of …well, where I am from. But Milkshake and you have problem too? WOW. :O
Yeah but I called the head of Aldrich customer service who got me to the head of their DEA-screening department who then got an earful from me (how they care far more about pleasing the government officials more than about their customers, and that i grew up in commie country and the officials there operated a lot like her department), this was at about 4pm on Thursday and the next morining, today at 10 am I got the bottle of sodium hypophosphite sitting on my bench. I run 2 two reductions with it and brought my material, all 12g of it, to the next step. So you see raising the pitchfork sometimes works in this country.
Way to go Milkshake.. Poke them more with the sharp pointy pitch fork…. Even after I get all the paper work done (and subjected to approval) I will still have to wait for 3 months… They cannot fly Acetic Anhydride, it must come by cruise…ship. Same goes for DIBAL. The shipping charges cost more than the DIBAL. Crazy….
here is how to make a fully-automated publication engine in Singapore: 1. Order a drum of acetic anhydride, get through the permits and wait until the boat arrives. 2. Few months later when you are finally in the possession of Ac2O drum (and you locked it away as to comply with the regulations) you let your faculty colleagues know that they can have some of it for their experiments, for a small admission price of you being included in the author list…
I am not making this up, I used to work for a man who – apart from being a secret police informant (StB was a Czech version of KGB) – made his long publication list by synthesizing L-tert-leucine once, and spooning off few grams of it to his peptide chemistry colleagues, for s nominal co-authorship fee. You see these biology papers have so many co-authors that including one who controls the supply of a key building block is not too hard.
Ha! Ha! I know. After all, I am sg’s immediate neighbour.. When my next paper is out, you can go ahead and count how many names is on it.
Hmm, it is extremely difficult to get chemicals in Singapore and you have to plan your synthesis at least 1-2 month ahead, and regulations are truly crazy, but I never heard about including anybody in a paper for chemicals, at least not in organic synthesis.
Ah… we might be neighbour… but strange things do happen.
Your story about “ethoxyethane” reminds me how I ordered Ac2O about 10 years ago in a beautiful town Kupavna. We bought about 20L of Ac2O, but in all documents and also during discussion with provider we both called it as “Special acetic acid”. Cool??? That was like a special code and I was like a James Bond at least.
wow. epic threadjack, milkshake.
life’s full of adversities but we do best we can under the circumstances. Congrats to your paper.
Great job checking for copper impurities!