Reduction of sodium hydride by fluorine gas in vacuum
November 24th, 2009 by LiqCIT is ON again: Na Promoted Aerobic Oxidation of Alcohols to Ketones, Tet. Lett., 2009, in press. [tx mt and Excimer][1]
I’m not quite in a position yet to judge English (but shouldn’t there be a hyphen in the title?) In fact, what pissed me off is the negligence that led to a blatant (in my view) typo in the abstract. It is not nickel (III) chloride that should be there, but nickel (II) chloride. Because nickel (III) chloride does not exist in the hands of people who manage to pull this shit off. It immediately gets oxidized to Ni (MMXII).
I don’t have problems with believing the chemistry. Shit happens, you know. Nickel and sodium metals under nitrogen will oxidize your mom. The reviewers have obviously had better things to do than paying attention. Or writing blog rants. Then, the confused reader is wondering: “Maybe it happened on quenching? Maybe their nitrogen was not pure?” and directs his attention to supplementary information. Which is? Bingo! Not there, ’cause it’s TetLett. I understand that you can’t tell everything there is in a four-page communication, and I’m sure that the authors are working on a follow-up, working so hard that they can’t even double-check what’s in the abstract of their fucking paper. They know it will attract attention, this is why they decided to work on it. Yet — they don’t give a fuck.
Just fucking shoot me. I just can’t express my concern with the fact that this kind of thing happens all the fucking time, everywhere. I’m telling you, twenty years from now, when the internet kids will raise their kids, the last grammar nazis will be prosecuted the same way as the actual nazis are. Then y’all be crying like spanked bitches. I really hope that fucking neutrinos become microwaves way before this, so that we build giant floating buckets of hope and go adrift off the shores of Himalayas.
No big deal? The consequences of chronic, ubiquitous neglect extend well beyond scientific publishing and writing. As it could’ve been put in Soviet Russia, today you neglect to notice a typo in the abstract of your paper, tomorrow you’ll sell the Motherland. In Soviet Russia, which might have suffered from neglect (among other things) more than any country in the world. I’m willing to go as far as blaming the failure of the cute little idea of communism on the fact that people don’t give a fuck, not because they’re evil or greedy as a society. Ok, I’d better wrap up now.
I kind of feel miserable sitting here and spewing shit for no apparent reason. Why did I spend an hour writing about it, and fifteen more minutes editing it, why do I give a fuck? What if I don’t? Will you?
[1] If the link doesn’t work, don’t blame me. I’m not the one who can’t make DOIs work for articles in press and publishes ISHTAR.
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You leave my mother out of this!
Nobody will be spared. We’re all going to die.
Ok, ok, jk. I feel better now.
Accepted manuscripts: these are articles that have been peer reviewed and accepted for publication by the Editorial Board. The articles have not yet been copy edited and/or formatted in the journal house style.
Going apeshit about NiCl3 on a manuscript that hasn’t been copyedited is a bit unnecessary. Yes, it’s a stupid mistake. But you pick your battles. The nickel(0) thing is… well, go bust out your glove box and get back to me.
That have been peer reviewed — you said it. It will be corrected, but at this point I have more faith in magical blogging powers than in the editors who may or may not be chemists.
I have never worked in a glove box, and I hope I never will. No disrespect, I just think there’s a lot to do under ambient atmosphere.
I have never worked in a glove box, and I hope I never will.
Keep your glovebox virginity as long as you can. It is precious! Do not allow the giant rubber hands to defile you as they have me!
Jeez, woman!
There, there. This too shall pass.
happens all the time – no need to go nuts and rant about one particular typo (are you stoned, btw?). and, anyway, why read Tet Lett and isn’t it what you’d expect from them? – Nature and Science are more fun, inspirational and ARE proofread.
cheers
I came to realize that all the things I come up with when I’m stoned are… bullshit. Drinking has been more much more eventful, more in a positive than in a negative way.
It just feels good to do this every now and then. Y’know, one thing layered on another, and I just couldn’t hold it. It happens VERY rarely. I like to think that it’s at least entertaining.
Cheers!
HAHAHA Love it. So angry! That rant may possibly be the fastest to get off topic.
The title reminds me of something funny. I had to do a 6-week long “original” research project when I took freshman chem. One group decided it’d be awesome to measure the speed of sound in vacuum. Research proposal was submitted, experiments done, data recorded and posters made. The TAs said nothing because they wanted to see what the kids would come up with.
All three members of the said group changed majors in the following semester.
LMAO!
What kind of data did you get?
I did not get what the problem is – is it just one typo? One typo in the abstract of something that “will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.” ???
Dear Al,
have you read the background at all?
I’m willing to bet all I’ve got and more that this typo would not have been fixed in the post-production without this post. Too bad you’ll have to come up with the time machine to prove me wrong.
Once again, the typo was just the trigger.
Himilayas
*ahem*
Himalayas?
Oh, snap.
Thanks!
Peer review in action!
Is it just me, or does this chemistry seem a bit improbable/impossible? Sodium metal is not going to oxidize ANYTHING… If it is the oxidant, than what is reduced?
More importantly, what is the rate of air oxidation of benzhydrol (or other related alcohols) back to ketones? Does 40 h sound about right?
In this case, screw the typos – how about the chemistry?!
Oh, I see your reference to the earlier posts now… Yeah, coupling the crappy chemistry with typos is a recipe for… Tetrahedron Letters?
I care about the mistakes in theory, because if there is no ability to distinguish research quality (which depends on reviewers and editors actually, like doing their jobs), then the literature and whatever other outlets there are for research become useless. If I have to recreate a validation of someone else’s research to do my job, well, then not much is going to get done by anyone. How long do you think it’ll take to develop those new drugs, plastics, solar cells, or cleaning products if people have to start from scratch to do so?
On the other hand, I don’t care about this so much because it’s TL. They’ve earned their reputation. If you can’t be bothered to read the title of the paper you’re reviewing or editing, and you actually keep your job, well, then I guess you and your journal deserve each other. (Unfortunately, I’ve seen misspelled titles and titles with nonexistent words in other eminent journals, and it drives me batty. Do you think that your readers are not going to notice the titles of your papers? Why can’t you use spellcheck on titles?)
I assume that sodium could generate the ketyl, and oxidation by Ni (with reoxidation by O2) could generate the ketone, whereas direct oxidation of the ketyl by O2 should generate peroxide intermediates which would either suck up more Na or generate peroxyhemiacetals which might not be so good. Do they get any pinacol products?
No mention of by-products.
They do it on 0.2 mmol scale – this is 0.4 mmol of Na, or 9.2 mg. I imagine this amount puts on a peroxide coat pretty rapidly. Moreover, they add in two 0.2 mmol (4.6 mg) portions, each cut up in small pieces “under nitrogen”.
I wonder if lithium content could influence how fast it gets oxidized. Lithium reacts with nitrogen, sodim doesn’t. Perhaps the lithium trace aids in corroding the metal piece, exposing it further to oxygen… anyone?
I don’t know how to react anymore. The chemistry works. We all know how to read between the lines, but it’s just… wrong to leave the discussion between the lines.
One of the authors is a real live professor in the United States, with tenure? (and a subsequent reputation to defend, I would hope.)
We are all guilty of an occasional pentavalent carbon, like retaining that extra angular methyl in testosterone to estradiol. Do penance by TAing a Chemistry for Nurses section. Trichloronickelate(II) is reasonable, [NiCl3]-. A guy wth a tail of alphabetic crap dangling after his surname ought to take more care, chemistry and language – or was it a privileged minority diversity hire? The Officially Sad must be emolumented not criticized, by law.
Elitism insists the better is preferable to the worse. Uncle Al is an elitist.
Corpus Christi. You do realize that that picture’s from Texas (of the world-beating educational system and its resultant products) and so the misspellings have lots of explanations…
it’s also photoshopped by a racist
I think the difference between you and me is that I’m an optimist. I believe there’s hope. Somewhere out there. Maybe.
really, though, this post is way out of order. it’s a typo. get over it & quit player-hating
1 of my least favorite things about reading chemistry blogs is the journal snobbery coming from grad students
Like I said, this does not happen to me often. I never liked bashing people or papers.
Oh, what the fuck, why am I explaining this.
From TotSyn:
http://www.thieme-connect.com/DOI/DOI10.1055/s-0029-1217115
What a…? Pd/C and NaBH4 yielding ketones and aldehydes??? A little bit contradictory to all I’ve learn so far….
Seems like it is not the first time those authors published that work :/
http://dx.doi.org/10.1055/s-2006-956457
Or try
http://www.thieme-connect.de/DOI/DOI?10.1055/s-2006-956457