WWWTP? – Sci-Fi Classic Edition

September 17th, 2012

It’s time to start attacking the ChemBark mailbag. Let’s begin with this little gem sent in by Excimer:

Photo credit: Excimer


Excimer writes:

I’m currently reading the sci-fi classic series Cities in Flight by James Blish, and hooray! there’s organic chemistry in it. Unfortunately, it looks like this.

Indeed. You’ve gotta love the: (i) Texas carbon, (ii) doubly-bonded hydrogen, and (iii) calcium–carbon bonds. I guess this sci-fi classic is heavier on the fiction than the science.

13 Responses to “WWWTP? – Sci-Fi Classic Edition”

  1. Anon Says:

    Perhaps not calcium: the a is subscripted.

  2. David P Says:

    The Texas carbon/double bond hydrogen looks more like a misprint to me, as they have everything else correct. The calcium is weird yes, but it has a valency of 2.

    The carbon-calcium bond is just not yet known. Open your mind to the possibility.

  3. qvxb Says:

    It would be appropriate to listen to Boston’s “More Than a Feeling” while reading Blish, since the album cover may have been inspired by his writings. http://en.wikipedia.org/wiki/File:BostonBoston.jpg

  4. swivel frits rule! Says:

    What about the hydrogen (is it atomic hydrogen, a proton, or a hydride?) floating by itself not bonded to anything in the top left portion of the molecule… my 1st semester organic students would love that on their first exam. I am sure it is a misprint but like the calcium-carbon bond the mind opens to the possibilities.

  5. Curious Wavefunction Says:

    The carbon-calcium bond is just not yet known.

    What about calcium carbide?

  6. TakeAChillPill Says:

    I understand that this is just a blog, but this post is one of the reason that people hate chemistry and chemists. Here me out and take what I say as not an attack on you, but the generally insular chemistry world with it’s atmosphere of superiority towards people who don’t get everything 100% right.

    1) I agree that the Texas carbon issue, as well as the dangling hydride, are misprints. Think of the situation: proofreaders and printers in the normal publishing world know nothing of proper valence. Moreover, requiring perfection in a time when printing chemical structures is somewhat presumptuous.

    2) While a C-Ca-S bond structure is strange, it is only so to you, a seasoned chemist. As stated by another blogger, Ca does have a valence of two, so why is this so strange? Once again, think of the layman – it’s pretty good for them! Moreover, the C-Ca bond is alpha to a carbonyl. Granted, the carbon is next to a nitrogen, but to a layman this is a pretty good extrapolation. If a ketone or aldehyde can be deprotonated at the alpha position, why not this molecule? Again, to us this may seem ridiculous, but to a layman its a really big step towards actual chemistry knowledge.

    In light of this, instead of critiquing the structure, it should be PRAISED as an attempt by a layman to get it correct. The amount of research that went into getting this correct was most likely long and well intentioned. To ridicule the book only serves to make chemists seem more arrogant and superior. No wonder everyone says they hate chemistry or can’t do it. This makes people run away from chemistry, or even worse be hostile towards it.

    Many posts in your blog are rightfully critical of the ‘Chemicals are bad!!” mentality. How can we combat this, by nitpicking well-intentioned attempts at correct chemical structures? This is not the door to a chemistry department, or a recruiting ad for a school. It is what it is – a fictional book with a chemical structure. How often do we see that, even if SLIGHTLY incorrect? Star Trek goes against a lot of physics, but it is stlll respected by physicists! But chemists seems fit to point out and ridicule any slight misrepresentation of a structure.

    Once again, this is not an attack on you, but a call to be more reasonable towards people who try to learn more about what we love – chemistry. Constant negativity and calling people out like this only serves to make laymen and young people want to be chemists even less. This blog, as well as many chemists in general, seem to lean towards this type of criticism. In my opinion, it does not seem to portray chemists in a good light.

  7. TakeAChillPill Says:

    *Hear, not here. Please excuse this slight error

  8. Paul Says:

    @TakeAChillPill: I believe I understand where you’re coming from, but I completely disagree with your analysis. First, this is a blog for chemists. I don’t think criticism on this blog leveled against a chemical structure from a book written a long time ago is going to deter many non-chemists from doing anything.

    On the other hand, I think that chemists will find this structure informative in terms of seeing, once again, the prevalence of errors made in structures in popular culture. We have a lot to do to improve chemical literacy of the general public.

    I think Star Trek and Breaking Bad do science fiction “right” by consulting with scientists to make the fiction more plausible. While writers can do anything they please, I don’t think chemistry is well served by having people jot out imaginative structures with tons of errors, so I am not going to go “PRAISE” them to use structures however they please and just be happy that they’re using chemistry, however perverted it may be.

    As an analogy, if you’re going to have a character in a movie speak Mandarin, why not use real words instead of having the guy say “ching, chong, ding, dong, kong”?

    I am all for encouraging writers to use chemistry, and I think *we as chemists should help them*. And while we are generally insular—that is a great point and I have written so in the past—I think that we are starting to get better. If a writer wanted to double-check a structure, she could easily post it on this blog, or chemmit, or a variety of other sites and get advice for free. I’d be happy to help.

    Finally, I think your analysis of the bonding in the weird structure is very generous. They could have put the Ca anywhere and justified it. in fact, if you are going to have the enolate serve as a ligand for Ca, I would favor showing the interaction at the oxygen (based on an argument rooted in HSAB and what you see in product ratios for O-vs-C attack by enolates on hard vs. soft electrophiles). Of course, I have not read the book—maybe I am jumping to conclusions and the bizarre structure makes perfect sense based on the plot. Somehow, I doubt it.

    Thanks for the comment and thoughtful dissent. I agree completely that we need to do more to foster a positive image of chemistry and part of that will involve incorporating more chemistry into pop culture. I just disagree entirely that WWWTP posts do more harm than good.

  9. vanad Says:

    why are you assuming this is calcium? that’s not what it says in the structure (C-subscript(a)-S). maybe it says it in the text, which i cannot read from here, but on the basis of the structure alone it looks like some undefined abbreviation. frankly I have seen much worse efforts than this in the mainstream chemical literature, meaning that I often often see misprinted/misdrawn structures (bonds, heteroatoms missing etc), cartoon blobs used in place of parts of structures, but also ambiguously drawn stereochemistry, wrong enantiomer drawn etc.

  10. Lyle Langley Says:

    “I think Star Trek and Breaking Bad do science fiction “right” by consulting with scientists to make the fiction more plausible.”

    It’s fiction, why does it need to be plausible? Star Trek’s Transporter is “plausible”?

    I know this is a blog only read by chemists, but the “look how stupid people are” – douchery is laughable.

  11. Andrew Says:

    This is clearly supposed to be a representation of disulfide linkages.

    The book was published in 2004 but I bet this diagram was copied from an old (text) book. I would not be surprised if the letters were typewritten with hand-drawn bonds (copied by a non-chemist) inserted.

    The CaS is really C2S, with a dodgy 2 on the typewriter which makes it look more like an a.

    Of course it should be -CSC- or more accurately -CH2SCH2-

  12. Anon Says:

    A disulfide is –S–S–.

  13. subnaught Says:

    Dimethyl Calcium reported in JACS in 1958: http://pubs.acs.org/doi/abs/10.1021/ja01552a081

    I thought you were an inorganic chemist?

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