Archive for the ‘Grammar & Style’ Category

The F Word

Tuesday, July 24th, 2012

You may have noticed that I don’t typically use profanity on this site. It’s not that I have anything against swear words—there is plenty of profanity in the comments here—I just don’t think you get enough bang for the buck with them in long pieces of prose. Written down, I find swear words are usually more distracting than effective at communicating ideas. In contrast, I find profanity to be much more useful in conversation, where you can shape the meaning of words phonetically.

So…what the hell I am babbling about? Well, it turns out that I have the dubious distinction of being the first person to use the “F-word” within the pages of Nature Chemistry. N-Chem has been playing down a man following Neil Withers’ move to Chemistry World, so Stu Cantrill has asked a few bloggers to help out with the monthly Blogroll column. Chemjobber wrote it last month, and I had the honor of writing it for the August 2012 issue. My contribution went live this morning.

Given that my use of profanity in a prestigious chemistry journal could raise some eyebrows, I wanted to take a couple of minutes to defend it. By “it”, I mean this:

Dr Rubidium, an analytical chemist who blogs at the Journal of Are You Fucking Kidding, contrasted several cases of homicide by the paralytic agent succinylcholine with its medical use in life-saving tracheal intubations ( Although that post was shockingly free of swear words, an ode to tetracyanoethylene (TCNE) on Carbon-Based Curiosities was as vulgar as it was informative (

As I understand it, the purpose of the Blogroll column is to promote interesting items and discussion on chemistry blogs to a wider audience (e.g., to stodgy old-timers who believe the Internet is full of garbage). Usually, the column covers any major subjects from the previous month and is then rounded out with one or two smaller items. My first draft for the column was due June 20th, and the major event that stuck out from the month previous was the splendid Favorite Toxic Chemicals carnival hosted by ScienceGeist.

I read through all of the contributions to the carnival, and the one that stuck out as the best was this one on succinylcholine. Naturally, I wanted to make this the example post of the column, but the name of its parent blog is the Journal of Are You Fucking Kidding. The traditional citation given to posts featured in the Blogroll column is (name of blogger) at (name of blog), so if I were to use it, Nature Chem was going to have to publish “Fucking”, censor the name of the blog, or change the typical citation format.

The more I thought about it, the more strongly I felt Dr. Rubidium’s post deserved to be the #1 representative of the carnival; it really is an interesting, well-written piece. My only question, at that point, was how to deal with the swear word. The three options, as I saw them, were to call the blog:

(1) the Journal of Are You Fucking Kidding

(2) the Journal of Are You F-cking Kidding


I ended up leaning towards option 1, because it was the proper, full name of the blog. You can’t replace a word in a proper name with a synonym or scrubbed letters without taking something away from the name. “F-cking” is different from “Fucking”. Since Dr. Rubidium often abbreviates her blog’s name as JAYFK, I thought option 3 was also fine, but less clear.

At this point, I e-mailed Stu (the editor) a couple of days before my draft was due and asked permission to use the F word. The ruling was not immediate; Stu conferred with the rest of the editorial team, and the decision was made that “Fucking”, in this context, was fine. One good point that was raised in their discussion was that some unsuspecting readers might be more offended by clicking a link to “JAYFK” rather than just seeing the F word in the text of the journal.

While I think the proper name argument alone is strong enough to win, I would also raise the point that this variation of the F word is among the most benign. Dr. Rubidium uses it as an adverb to modify “kidding”. To me, this embodiment should count as less offensive than its use as a gerund.

Once the succinylcholine post was chosen as the centerpiece, I decided to highlight Excimer’s tetracyanoethylene post, because in addition to its being informative and entertaining, I could juxtapose this truly vulgar piece against the JAYFK post. And while there were a number of other really nice posts that could have been mentioned, the whole column is only 300 words, so I had to be picky. Sorry. For the closing part of the column, I thought that the traditional old fogeys who only read journals and never read blogs might have their interest piqued by the latest round of discussion of the death of organic synthesis. That’s always a topic that gets people going.

Anyway, that’s the behind-the-scenes tour for this month’s (possibly offensive) Blogroll column. At the end of the day, will people care about one swear word in a chemistry journal?

If so, they can f— off.


Friday, August 13th, 2010

“Grad student” is short for “graduate student.”  That is pretty obvious, and any chemist who doesn’t know as much has probably inhaled too many solvent vapors.  While it might be a bit more complicated, I am continually amazed by how many people in our field  misunderstand and misuse the term “postdoc” in both conversation and writing.

So, let’s get some things straight:

  • The term “postdoc” is a shortened version of postdoctoral scholar or postdoctoral fellow.  I imagine there are other administrative variations in how institutions identify those engaged in postdoctoral research, but those two titles are pretty standard.

Minor usage note:  In my book, all postdocs are postdoctoral scholars, but only those who hold funded fellowships are postdoctoral fellows.

Usage note:  “Postdoc” is a colloquial term and should not be used in formal documents like CVs.  Instead, “postdoctoral scholar” (or the equivalent) should be used.

Major usage note:  Postdoctoral scholars and postdoctoral fellows should hesitate to use their full titles in everyday conversation.  “Postdoc” is sufficient.  Anyone who introduces himself as a “postdoctoral scholar” is a pompous twerp.


  • Postdoc can be used both as a noun (the position) and a verb (to serve in that position)


  • The grammatical and orthographical rules of English still apply to the term postdoc.  Remember, when conjugating postdoc for its use as a verb, you may have to add a “k”.  For instance:

Guido is a postdoc for Erick C.
Guido postdocs for Erick C.
Guido is postdocking for Erick C.

And after Guido is terminated for not working 100 hours/week…

Guido postdocked for Erick C.


I’m not just making this crap up; the same rules apply to the verbs frolic, mimic, panic, picnic, and traffic

The variations “postdoced”, “postdocing”, and “postdoccing”  are plain wrong, and using them will make people think less of you.  Sadly, even Science Magazine and the National Postdoctoral Association royally screw this up.

I guess English Ph.D.s don’t postdoc.

I Judge People By Their Grammar and Knowledge of Phenol

Saturday, March 10th, 2007

Some commenters in a previous thread took umbrage at the fact that I admit to judging people by their grammar. Well, I do, and I’m not going to change anytime soon. I’ll put poor grammar on par with poor hygiene, dressing like a slob, and bad table manners—while they don’t automatically invalidate a person’s ideas, they will cause me to treat anything the person says with more skepticism than usual. With respect to the four errors I found in the first paragraph of this recent paper from Org. Lett., the misplaced apostrophe in “Evan’s” was the most aggravating. While the chemistry in the paper was good, as The Chem Blog has noted, the authors’ lack of attention to detail was borderline disrespectful. I expected more from one of the most storied labs in synthetic organic chemistry.

A lot of people will complain, “So what if I make a few mistakes? Why don’t you focus on the ideas?” That’s the thing: I want to focus on your ideas, so why don’t you stop whining and learn to write properly? The rules of grammar are not up for discussion—just follow them out of courtesy to your readers. Grammatical errors are distracting and will cause them to lose sight of what you’re writing. If you are someone who has no trouble reading documents riddled with mistakes, that’s great, but when you are writing, you aren’t writing for yourself.

While grammar shouldn’t be the sole criterion for evaluating intelligence, I will admit to judging some things by a relatively obscure set of criteria. For instance, I have a list of favorite subjects for judging textbooks and course packets. One of the first things I do to determine the quality of a sophomore organic textbook is to look in the index for phenol. As you all know, phenol is more acidic than “standard” aliphatic alcohols. If you took a survey, most people would ascribe this fact to a resonance effect by drawing the following structures:

There are a number of variations on this theme, including drawing out all of the unhybridized p orbitals and showing that an orbital on oxygen containing a lone pair can overlap with the pi system, thereby allowing for increased delocalization of the extra negative charge density.

It turns out that an inductive effect—not a resonance effect—is the predominant reason for the increased acidity of phenol relative to aliphatic alcohols. Whereas aliphatic alcohols have a C(sp3)—O bond, the carbon to which the hydroxyl group is bonded in phenol is sp2 hybridized. The increased s-character of the carbon orbital used to form the C—O bond makes it more electron withdrawing, which leads to greater stabilization of the conjugate base of the alcohol. For the purpose of comparison, look at the pKa of phenol compared to that of enol tautomer of acetone:

Even though you can only draw two resonance forms showing delocalization of the extra negative charge in the conjugate base of the enol (vs. four for phenol), the acidities of the two protons differ by less than an order of magnitude. For those interested, these data come from Evans’ Chem 206 lecture notes (Lecture 20, restricted access), where the point is hammered home in glorious detail. Professor Evans’ PowerPoint slides should be framed and displayed in the Smithsonian.

While we’re discussing phenol and errors, let me also use this example to illustrate one of the main problems with Wikipedia. Wikipedia is great, but it is home to a number of edit-happy users who think they know more than they actually do. If you look at the discussion page for phenol, someone actually addressed the resonance vs. inductive effect argument, but was unceremoniously (mis)corrected by another user, who references an incorrect explanation on the Internet. Thus, the main article (as of today) gives the incorrect (resonance > inductive) explanation:

Phenol has a limited solubility in water (8.3 g/100 ml). It is slightly acidic: the phenol molecule has weak tendencies to lose the H+ ion from the hydroxyl group, resulting in the highly water-soluble phenoxide anion C6H5O. Compared to aliphatic alcohols, phenol shows much higher acidity; it even reacts with NaOH to lose H+ whereas aliphatic alcohols do not. This is due to orbital overlap between the oxygen’s lone pairs and the aromatic system, which delocalizes the negative charge throughout the ring and stabilizes the anion. This effect is attenuated, however, due to oxygen’s relatively high electronegativity. [1]

God knows that we in the chemical blogosphere love the Wikipedia, but read it with skepticism.

This concludes today’s lesson. Your homework for the weekend is to find all of the grammatical errors in this post. For extra credit, find an error in a chemistry article on Wikipedia, fix it, and brag about having done so in the comments. Class dismissed.