Tuesday, February 12, 2013

Stop using that word: Facile

Certain words tend to catch on in the scientific literature, such as "novel", which increased exponentially in usage starting in the 1980s. One of those catchy words is one that I previously* used like candy: facile.

Chemists like to describe reactions as "facile." By that, they usually mean easily-performed, smooth, or simple. You know, not much fuss involved. And indeed, that's one of the definitions (from the OED):
adj. (1) a. That can be achieved with little effort; straightforward, easy. In later used freq. in disparaging sense: contemptibly easy. b. Of instructions, a device, etc.: easy to understand or make use of; simple. c. Of a course of action, a method, etc.: presenting few difficulties.
That is the original, historical meaning. Another (more modern) definition carries a different implication (from the Oxford Pocket Dictionary):
adj. (1) ignoring the true complexities of an issue; superficial; or (2) (of a person) having a superficial or simplistic knowledge or approach
And if you type "facile" into Google, you get this immediately:
adj. (esp. of a theory or argument) Appearing neat and comprehensive only by ignoring the true complexities of an issue; superficial
Essentially, "facile" in modern usage (last century or so) has a negative connotation. And take a look at the synonyms for facile (Oxford again):
simplistic, superficial, oversimple, oversimplified, schematic, black and white; shallow, pat, glib, slick, jejune, naive
It's interesting to note that wiktionary has a chemistry-specific entry for "facile":
(chemistry) Of a reaction or other process, taking place readily.
Of course, language is defined by usage, so maybe I'm being picky here. But why not describe procedures as "straightforward", "robust", "easily performed", or any number of other, less ambiguous descriptors? (My intuition says those terms sound too common/"blue-collar" to many academics)

When did "facile" catch on? Well, from a crude PubMed search, it looks like the late 1990s was the tipping point (incidentally, PubMed makes it way easier than SciFinder to get data on this kind of thing. Sorry, CAS). Additionally, most of these references are (not surprisingly) from synthetic organic chemistry papers. See also this description of the two meanings of the word and their historical context.

The shrouded meaning of facile adds overlooked complication when authors start to invent words (after all, organic chemists are wont to derivatize things). There's a handful of examples from the literature that use "nonfacile" (which isn't even a word; go ahead, check the OED or Merriam-Webster).

Take this example from an otherwise-good trifluoroborate-preparation paper (Lennox, A.J.J., Lloyd-Jones, G.C. Angew. Chem. Int. Ed. 2012, 51(37), 9385-9388. doi: 10.1002/anie.201203930):
Replacing MeOH with diethyl ether led to co-precipitation of 2a with other potassium salts (KF/RCO2K etc.), thus making isolation of pure 2a nonfacile. Switching to MeCN kept trifluoroborate 2a in solution, but an excess of carboxylic acid (e.g. acetic or ortho-iodobenzoic acid) was still required (Scheme 2).
So if "facile" means "contemptibly easy" or "appearing neat and comprehensive only by ignoring the true complexities of an issue", what does "nonfacile" mean? Was isolation of 2a not contemptibly easy (just acceptably easy?). Did isolation merely appear difficult while really, under the surface, it was simple?

Stop using that word.

* i.e. before a reviewer pointed out the proper definition.


  1. Then there's the issue of how to pronounce facile...

  2. You, and your reviewer, are unduly hung up on the fact that “facile” has more than one definition and one of those definitions doesn’t quite fit the description of a robust, straightforward and easily performed chemical synthesis. But context is everything and if you say a reaction is “facile” nobody is going to think that you are suggesting that your reaction is superficial or possessing of a simplistic knowledge. The word “discriminate” also has multiple meanings, but when I say that I have “discriminating taste in music” everybody knows that it means I don’t listen to Justin Bieber and not that I don’t listen to Miles Davis. I would argue that “facile” is, in fact, less ambiguous than “straightforward,” “robust,” or “easily performed”, precisely because of its prevalence in the literature. While all these words technically mean more or less the same thing, “facile” has developed a connotation that implies more easily than “easily performed.” In other words, so easy a caveman (or even I) could do it. Also, facile rhymes with hassle.

    1. the same goes for "exploit." why are organic chemists always exploiting certain types of reactivity? at this point, shouldn't the reactivity know better?

    2. Good point about the “exploitation” in chemical synthesis literature. I should also add that despite the fact that I regularly “employ” certain reactions, reagents and even chemical principles, none receive benefits or wages. I’d also point out that the word “simple” which is suggested (in adverb form) as a replacement for “facile” also has multiple definitions including “unsophisticated, naive and stupid.” Perhaps this post should have been about how unhelpful it is (and inappropriate?) for reviewers to address stylistic-rather than technical-issues.

    3. Good points on all accounts. As to "facile", outside organic synthesis it usually means (as in the first definition) "contemptibly easy" -- i.e. in broad usage it tends to be derogatory. So I can't quite bring myself to not be a little irked at its use within the discipline. I understand the "everyone uses it to mean X" argument--and I'm certainly not saying it's being broadly misinterpreted by readers of the literature. But at the same time, one of the tenets of scientific communication is to eliminate ambiguity in the name of clarity--I just recommend keeping alternate common-use definitions in mind when writing technical literature.

      I do want to address your second point about it being unhelpful for reviewers to address stylistic vs technical issues (this might become a subject of a later post). I don't think it's inappropriate or unhelpful. There are numerous instances where bad style gets in the way of understanding: (1) an author has poor command of English, leading to awkward phrasing that is grammatically correct but difficult to read/parse; (2) the work is readable but language is overly flowery [inefficient and pretentious] or harshly curt [jarring and cold]; or (3) an idea can be presented in a more fluid manner via sentence restructuring. The principles of rhetoric are applicable to science, else we wouldn't bother writing journal articles at all and would just scan our PowerPoint slides and Tweet them to each other.

      To get at what I think the thrust of your comment is, though: a real disservice occurs when those reviewers who fancy themselves to be good writers (i.e. they're really just good spellers) think correcting diction and spelling counts as thoughtful reviewing. Like you're hinting at, content is foremost. In the world of writing pedagogy, tutors are taught to help revision of "higher-order" (scientific argument, broad organization) concerns and to ignore "lower-order" concerns (grammar, punctuation) until last. Reviewers usually receive no such training, and it's easy to be tempted by the "quick fixes" of simply rewording sentences.

      And it's pronounced "fah-KEY-lee", obviously.

  3. I think that the use of "facile" to indicate an easy reaction stems from the Spanish word "fácil" which means easy. It may have negative connotations in English, but not at all in Spanish. There are lots of words like this in Organic Chemistry, aren't there? For example, "sinister" to describe counter-clockwise chiral centers: sinister has a very negative denotation in English, but it stems from the Latin root "sinister" which simply means left. Or when we describe a substituent as being "gauche" to another substituent of a Newman projection; gauche means left in French. Though there is no connotation in English for gauche, it is very clear that many of the words in Organic Chemistry (and English for that matter!) are directly borrowed from other languages, where they carry different denotations and connotations. I don't think it's necessary at all to discontinue their use simply because they carry different meaning in common vernacular versus in scientific language. After all, the majority of words and phrases used in the sciences do have different definitions than when applied in non-scientific ways.