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The Scientific Literature

CA Days

A brief discussion the other day on Twitter got me to thinking about the lost world of literature searching – back when everything was bound journals and paper. My whole grad school career took place in the pre-PDF world, and a good part of it was pre-CAS Online. So those of you from that era will well recall what it was like to search things in the 5-year Chemical Abstracts “Collective Index” volumes.

When I started out, the most recent of those was the 10th collective index, covering 1977-1981 literature. That got more and more painful to use, with constant recourse to the paper-bound updated index volumes, until the 11th CI showed up covering 1982-1986. So in my head the 11th was always “the new one”. I naturally spent an awful lot of time with the 9th and 10th CI sets. The 8th as well, although it was noticeably a bit smaller than the others, and once in a while I’d dip into the earlier ones. A couple of years into my first job in industry the 12th CI came out, and that’s the last one that I really used in hard copy and by the old methods. What old methods were those?

Well, finding an individual compound, in “Hey, has anyone made this?” mode generally involved hitting the Formula Index first, which gave you a confirmation of anything with that empirical formula existing (for one thing) and a look at what the CAS people had named it as. I suspected that their long-term goal was to name every organic compound as a derivative of methane, personally. What you’d find, though, was some root name that you could trust for various substituents (“3-chloro” or the like), but if you decided that you wanted to search a COOH substituent at some position, the name completely flipped around to prioritized that group. (I also suspected that the long-term goal of CAS was to name every carboxylate derivative with an aliphatic carbon next to it as a derivative of acetic acid). So you had to be ready to run a multi-pronged search to get your naming conventions down before heading into the other index volumes to look those up.

You could, of course, get abstract entries from just the Formula Index, but the Name/Chemical Substance Index volumes would give you a look at all those derivatives as well (as long as they fit the same naming scheme), and that could be valuable for a sort of primitive substructure/derivative search. Either way, you’d be sent back to the actual abstract volumes to see a one-paragraph summary that would give you the literature reference itself and an idea of whether you wanted to go look it up. I used to generate all sorts of pieces of scrap paper with those abstract citations on them while rooting through the indices, then I’d take them in order as I worked through the bound abstract volumes, noting down the actual journal citations for the ones that seemed worthwhile. There are surely some of those in my oldest paper files, which I saved for just that reason (all the other paper files went away some years ago, in oddly cathartic sessions down by the recycling bins).

Once you had the journal citations, it was back into the shelves of the chemistry library. Duke’s was quite good, and had a lot of full runs of journals going back to God-knows-when. What strikes me, looking back, is the amount of page-flipping. All those index volumes, all those abstract volumes, all those bound journal volumes, flip, flip, flip, flip. That was the sound of a scientific library – people flipping pages looking for papers. When I found a good one, I’d haul it up to the photocopier, plug in the little counter thingie that charged copies to our research group, and do a motion that became automatic over the years. Push the page of the bound volume’s paper up to the edge of the copier glass, hit the button, generate a page, turn the volume around end-to-end and push the second page up against the edge, hit the button, flip and rotate and push and flip and rotate. This, of course, generated a stack of copied pages that alternated being right-side-up and upside-down page by page, so you’d take the stack off the side of the copier and rearrange them before stapling them together.

Fancier copiers had a “bound volume” mode, with a line marked towards the middle of the platen glass for you to put the page-break valley on. It would then do a double-scan, first one side of the divide and then the other, which certainly saved time. It was set for a full-sized journal volume, so if you were copying off something from a smaller-format publication like Chemische Berichte there would be a big margin of black around each copied page. Sometimes these black margins would be enlivened by ghostly photocopies of your own fingers holding things in place.

The bound volumes, naturally, were supposed to be returned to the shelves. But there were always some piled up in the copier room (and perhaps various other flat surfaces around the place as well), so you could well find a gap in the procession of volumes when you went to look something up, and would have to wander through the library looking for it. I did a lot of wandering around in there anyway, because I found some of the volumes interesting from a historical point of view. For example, I never recall finding many useful citations for my own research in the Anales de la Real Sociedad Española de Física y Química, but it was unnerving to see the size of its bound volumes on the shelf drastically shrink in size when the Spanish Civil War began in 1936, ceasing publication altogether for a while in 1938 as I recall. Then when things picked up again, you opened the first resumed volume to be greeted by a frontspiece of Francisco Franco and a shining cross, in case you had any doubt about who won the war. Similarly, the numerous German journals showed the strain of the Second World War as it went on, becoming smaller, thinner, and printed on increasingly nasty grades of paper. I recall an issue of Die Chemie, the wartime name for Angewandte Chemie, with a message from Albert Speer (signed simply “Speer”) printed on the cover, all about production goals and the like. The German journals tended to lurch to a halt during 1945 – of course they did – and only resumed, in many cases, in 1947.

As for Chemical Abstracts, by the time the 13th Collective Index came out for the literature up to 1996, I was using SciFinder instead of rooting through the paper volumes, and (like the rest of the chemical world with such access) I never looked back. There was a 14th CI, and I may have seen that in some library somewhere, but I’m not sure. And there was even a 15th in hard copy, a quaint and forlorn effort by that time. I’m positive that I’ve never seen one, and I wonder how many of them even exist. And that was that – the paper form of CA disappeared in 2009, and there was thus no 16th Collective Index at all. Who’d have thought?

 

45 comments on “CA Days”

  1. Some idiot says:

    And Beilstein… Don’t forget Beilstein!!! 🙂

    1. Russ says:

      Houben-Weyl!

    2. 10 Fingers says:

      Ooof. Yes.

      I will never forget a journey through Beilstein to an 1899 Chem. Ber. prep that I (painfully slowly) translated. I was a little proud of myself until it was clear that my reaction completely failed. Certain that it couldn’t be because I did anything wrong (/s), I puzzled over this for some time. Finally, I realized that the state of my reagents in 1899 was unlikely to be the 99% pure form that I ordered from Aldrich, and eventually that the best they likely had was an aqueous solution (and that the prep didn’t mention this as it was well-known to practitioners of the art then, as they say…). Dilute to 30%, and the reaction worked perfectly.

      A lesson in many things, humility among them.

    3. Isaac Asimov has a lovely little short story, a murder mystery, which hinges on Beilstein!

    4. Sylvia says:

      ah…Beilstein….I remember those days. I was one of the writers of the “Beilstein Handbook” before a miracle transformed my career path. To create the Beilstein Handbook articles we wrote with pencils on small strips of paper. Extracted data and synthesis steps exactly as printed in publications, error checked, used our scientifically educated brains to judge whether a synthesis was really what was printed etc.. It was a massive process, involving almost 100 writers, their editors, a department to nothing else but create proper nomenclature and others who sorted those hundred thousands of paper strips so an article could be printed. It makes me fee like a fossil when I think back like “whoa I did what?”

      Thank you. I love that you pointed Beilstein out 🙂 nice the name is not forgotten!

  2. Bob Seevers says:

    Derek, you have done a nice job of capturing the sheer grunt work of a literature search. My thesis advisor, Ray Counsel at the University of Michigan, was an idea a minute kind of guy. In self-defense, I developed a three-tiered strategy. The first time I heard an idea I would nod and make a note to myself. The second time the same idea came up, meant that I would take myself to the library and do the appropriate literature search to see what had been done by others. Only if I heard the same idea three times from Ray did I start working on it in the lab. Over my five & a half years this strategy served me well.

  3. Isidore says:

    Then, sometime in the early 1980s, Eugene Garfield’s “Current Contents” came about and made it much easier to keep up, with the titles, at least, of journals in a relatively broad area of research.

  4. neo says:

    I watched Shoemaker-Levy 9 impact Jupiter on a computer terminal in the same room as you did your manual CA searching, so I can confirm that the internet did eventually make its way to the Gross chemistry library.

  5. Dr. Manhattan says:

    You forgot to mention the inevitable blurring of the copy at the binding if the paper was in the middle of a very thick bound copy….

  6. MTK says:

    Back in the day I perfected a photocopying technique that improved efficiency.

    a) copy back to front for any article so they ended up in the right order. (Our copiers always spit out the copy printed side up.)
    b) select 2 copies rather than 1
    c) position the journal or bound volume as usual but after the scanner made the first pass and was repositioning itself, quickly move the journal over so that copy #2 would be the second page.

    All of this resulted in hitting “copy” 50% less often and all pages being in the proper order and same orientation.

    Good times!

  7. navarro says:

    i remember taking advanced inorganic, which i took as an elective because of my intense difficulties with organic chemistry (long story but basically i never worked harder for an “F” in my life). The first assignment was a literature search and i drew “sodium anions.” i went through the most recent edition of chemabstracts and found six or seven articles so i copied down the references in the appropriate format along with copies of the abstracts and turned it in. everything seemed great but i made an 80. in the margin he wrote a citation for a particular article along with the notation “-20”. i asked what was up with that and he said that while i had found all but one of the relevant articles in the literature i had missed the most important article. the article itself had been dropped by mistake from the most recent edition of ca but if i had gone to the one before it, or any of the ones before it, it would have been there. then he asked a devastating question– “did you happen to notice that article was listed first in the bibliography of every other article on the phenomenon?”

    1. Anonymous says:

      Originally (1907), Chem Abs was prepared by professional abstracters who would read the articles and write the abstracts themselves. Lots of old abstracts have details taken from the body of the article, not just the basic intro. Into the 80s and 90s, journals started requiring author written abstracts that would be suitable for direct (and automated) inclusion in the relevant databases. Bye bye abstracters.

      I had the good fortune to be in big cities where I had access to great libraries, even in high school. I went to college in Boston and had access to the MIT, Harvard (Cambridge and Countway Library at the Med School), and several teaching hospital and other libraries. Those combined libraries were fantastic. The Harvard Chem Lib was beautiful but, as luysii pointed out, it is now a fraction of its former self having been substantially converted into labs and offices. Woodward’s office was directly across from the Chem Lib and I’m sure he used it a lot.

      I had easy access to Chem Abs, Index Medicus (which became pubmed), Biological Abstracts, Science Citation Index and its extra parts (Index Chemicus, Current Chemical Reactions) and so on. I worked for a guy who subscribed to Current Contents and it circulated through the lab when he was done with it. (NOTE: Science Citation Index started in 1964, not the 1980s. I think Current Contents also started in the 1960s. I got to know Garfield in the 1990s during correspondence about some matters in the history of science and “Citation Classics”. In particular, the flash paper by Clark Still, JOC, 1978, is a very highly cited paper but I don’t think it was ever recognized as a Citation Classic (someone please check that – I do not have lit access at this time). I think it was because Still didn’t want to write an essay about the paper and its significance. Garfield was a very nice and helpful in our correspondence and conversations.)

      It used to be that you could subscribe to individual “sections” of CA very cheaply, e.g., the Organic Section. (I subscribed as a grad student.) I forget: was it monthly or bi-monthly?

      Derek mentioned the non-obvious ways that compounds might be compiled in Chem Abs. IMO, Beilstein was even wackier. My German is not so good, but I had the user handbooks and guides to using Beilstein and Patterson’s German-English Dictionary for Chemists (which I still have). I found a LOT of good manually abstracted info in Beilstein. (It was mostly an index of chemical compounds, not chemical literature, so MP, BP, and other compound info was in there.) Beilstein went to publishing in English in the 90s. Gmelin is sort of the inorganickers’ Beilstein.

      I also loved to use (the now defunct) Theilheimer’s Synthetic Methods for two reasons: (1) it had another unusual indexing system that I knew how to use very well (that many others did not have the patience to learn) and (2) the “Trends” section of each annual volume. HOW GOOD WAS THEILHEIMER AT IDENTIFYING (or misidentifying) IMPORTANT PAPERS IN THE TRENDS SECTION? Back then, each volume of Theilheimer was around $400-$500 and a PI I worked for had a complete set. But he would tell his foreign postdocs to buy him the cheap ($40-$50) knockoff copies from Japan or India (that was in the 80s, before Japan agreed to comply with Int’l copyright laws) before moving stateside to his lab.

      Something that all should be aware of: THE INDEXES AND ABSTRACTS ARE NOT COMPLETE!! You will surely find compounds in the primary literature that are not abstracted in Chem Abs or elsewhere. The humans and software programs simply do not get them all. I used to be able to rattle off quite a few examples. Also, they make mistakes!! Despite the structure encoding and check digits and all the rest, sometimes the structure being searched was entered incorrectly or the structure you find in CA cannot be found in the cited paper. Do not rely on the indices alone and neglect reading the primary literature.

  8. Leucine says:

    The current generation can’t even relate to what we all went through. I think in a way we are all lucky to have the experiences of the past and present. Literature search used to take good 6 months to understand what had been done and what can be done on your project/synthesis. Everything got sophisticated and simpler …exciting days for developing novel reactions/reagents/synthesis etc, however, short of funds. I am sure it is the case with the other fields as well. I think China and India are doing by pouring excessive funds in to scientific research at right time than the flat budgets of NSF and NIH of US.

  9. luysii says:

    The following dates back to Graduate alumni day at Harvard in 1962

    Libraries have certainly changed. The library in the Harvard Chemistry Building is a beautiful wood paneled affair with comfortable chairs and big elegant wooden tables. All the returnees on our tour of the department wanted to see it. The graduate student leading our group noted that she almost never goes there, getting what she wants from her computer.

    The library was unchanged, except for the fact that there was no one in it about 11AM. The librarian came out of her den anxious to talk to a few living breathing humans, and wouldn’t let us go. Solitary confinement is hell.

    Most of you are too old to remember the Jack Benny radio show, but the poor librarian was like the denizen of ‘the vault’ — one of Jack Benny’s gags where he kept all his money guarded by numerous traps and an old man who had not been out of the vault in decades.

    1. luysii says:

      2012 not 1962 sorry

  10. anon says:

    the Chem Library in old Venable at UNC had a spiral staircase, and it was the only part of the whole building that didn’t smell like natural gas.

    No microfilm or microfiche readers at the library in Gross?

  11. Steve says:

    Derek,
    you forgot the key loop step. Copy down the numbers from the 5 year index, go to the individual entry, find you had copied a number down wrong, return to the 5 year index, repeat

  12. Christophe Verlinde says:

    Not only do I vividly remember the laborious searching through the CA tomes but also the shelves with new issues of the most obscure sounding journals. One was called “Fette, Seife und Anstreichmittel”. I just found out that it still exists, but with a new name “European Journal of Lipid Science” – how boring, give me the old name.

    1. LF Velez says:

      The lipid sciences texts have been through a lot of changes over the last 40 years, as I learned to my horror as I helped update a chapter for a reference book. Extra fun when the old citations didn’t use the full journal title because ‘everyone’ knew what “Fett” should mean!

  13. MoMo says:

    I miss the smell of ozone coming from the copiers at the Hayden MIT library on a Sunday morning.

    Todays scientists wont ever know the joy of crawling the stacks and seeing the exotic scientific topics in the books and journals housed there.

    Went back there recently and the place was empty.

    1. Anonymous says:

      MIT Hayden Copiers: I could not believe that the MIT Libraries stuck with old fashioned wet process copiers for so long. I always figured it was some kind of kickback deal or that the Library Director owned stock in that company.

    2. Isidore says:

      This brings back memories! I spent so much time in the Hayden Library I ended up going out for a few dates with one of the librarians. And the upper floor housed the humanities library, which had many current non-science magazines, a good place to take a short break or a short nap.

      1. Anonymous says:

        The Great Dome (the picture post card view) of MIT housed the MIT Barker Engineering Library. The book stacks wrapped around the perimeter on 3 (or was it 4?) floors. The new periodicals / reading room was directly under the dome and had deep comfy chairs. I could not read in there; as soon as I sank into a chair, it was lights out for me. It seems it is now a study space and I have linked a photo in my handle.

  14. Martin Stoermer says:

    I remain in awe of the people at CAS extracting chemical structures from an ever-expanding chemical literature in those days

    1. 361 says:

      While I agree with you. I do not think it is 100% guaranteed that the scifinder or Reaxys type of tools that we have are as reliable. It does not make me comfortable to think it does not exist if it is not popped out on scifinder or reaxys. There are always some typos and misleading on scifinder and reaxys which make feel that there can be omissions as well because I feel it is the manual entry. There should be some mechanism in place where any published research should automatically be indexed/documented in those search tools so that there is no lapse. What do I know about inner workings of those search engines….so just my ramblings.

  15. dearieme says:

    (1) I remember the joy of first using the Scientific Citation Index.

    (2) I was required to demonstrate a competent reading knowledge of a modern foreign language of relevance to science. It was infra dig to use a language you’d learned in secondary school. And so it was that I learned to read German. I did consider Russian but then decided that the USSR would prove to be a flash in the pan.

  16. Chacko Jacob says:

    I remember in 1977, at the library of the Indian Institute of Science, Bangalore, finding the 1905 volumes of Annalen der Physik, with Einstein’s papers. I wonder if they are still there?

  17. The ghost of bridgehead heterocycles past says:

    Ah those were the days when those that could knew their imidazo[1,2-a]pyridine from their imidazo[4,5-b]pyridine and those that couldn’t didn’t know their azole from their arsehole…

  18. LDP says:

    Let’s not forget the high value in that era of the PI’s “little black book” or our individual recipe card boxes of references.

  19. Diver dude says:

    Index Medicus. ‘Nuff said.

    But I have encountered more thought provoking things by simply reading the article next to the one I was looking for than by any other means.

    1. Louis says:

      This!

      The sheer pleasure of hunting a compound or reference down, was one thing. Sure the “pleasure” was a pain in the neck sometimes, but more often than not I’d end up spending at least one additional hour reading around as I’d discovered something interesting by accident.

      This still happens, but it’s quicker to find the “idea stimulating” novelty (and for some reason the increase in time spent reading around has increased to compensate for the search time saved)

      1. Nick K says:

        Good point. While computerisation has made searching for compounds infinitely faster and easier, it has also made the serendipitous discovery of new reactions and chemistry almost impossible. I once found the ideal reagent for a transformation quite by chance while looking for something else.

    2. loupgarous says:

      As an undergrad in biomedical engineering in the 1980s, I was introduced to ebola and marburg viruses while researching different things physically adjacent to reviews of the literature (and in one case, a bound set of papers on the work extant to that time on marburg, which was great for following how understanding of what filoviruses WERE gradually increased as electron microscopes got better, and details of protein structure were gradually teased out).

      University administrators are wrong there – the elective system isn’t necessary for “broadening” the minds of technical undergraduates. A good university library (and those were mostly good in the universities of Louisiana, I’ve used them stretching from Louisiana Tech’s in the northwest to those of LSU and Tulane Medical Schools in New Orleans) put to work by someone with good research skills would, over a few years, broaden one’s knowledge quite a bit.

      Of course, the Internet does so even more markedly, to the point one sometimes has to not indulge one’s lateral thinking bump when looking things up.

  20. Chris Phoenix says:

    A few years ago I strolled into a public library and wanted to find a book. I momentarily didn’t remember the modern phrase for computer-with-catalog, so I asked a librarian where the card catalog was.

    She was completely unfamiliar with the term “card catalog.”

    1. El Tordo says:

      Back in early 1980, my first chemistry-related paid job was for the Analytical Chemistry department professor, writing *in pencil* cards with summaries of CA reports on new analytical methods for trace analysis.
      As I didn’t speak English, i had my Spanish-English dictionary (almost as big as a CA volume!) always with me.
      So, i was triple dipping: learning chemistry, learning English and making a few pesos. The latter were quickly invested at the science bookstore.
      I’ve been lucky to find at such early age one of my passions. I’m grateful to those who gave me the opportunity to grow them.

  21. rhodium says:

    Before Current Contents, which was a godsend, I would try to keep up with the literature by looking for papers from people I knew. I would scan the references for papers I should read. Another oldie: reprint request cards. Getting them when I started out made me feel like a grownup. Finally, recalling photocopies, journals like Chemical Soviety Reviews that could be copied two pages at a time were favorites.

  22. yuriwho says:

    Oh the delight when finding an Org. Syn. Prep. for a compound you needed but couldn’t afford. Also, Natural Product Reports was fruitful lunch and bathroom break reading.

  23. When I was a mathematics grad student I eventually got around to wondering Just How Far Back from of the journals went. Suffice it to say I found Galois’ paper about field extension, in a beautiful leather bound journal volume.

  24. Anonymous says:

    The Columbia chemistry library had Comptes rendus back to the late 18th century. Somehow that impressed me since the chemical papers predated atomic theory by twenty years. It had a complete run of Chemische Berichte including through both World Wars. The war year volumes were all stamped “property of the custodian of alien property”. I always imagined a spy flying to Zurich, buying them from a science book store and flying back to Lisbon with the journals stuffed into his pants. As I recall there was no May, 1945 issue but they started back up in June.

    1. Nick K says:

      The Chemistry Department at Penn also had Comptes Rendus going back to Lavoisier’s era. It was a huge thrill to read the papers on combustion and respiration in his own words.

  25. Thomas McEntee says:

    The habits I learned doing CA-based literature searches in the mid-1960s have been immeasurably valuable. It became quickly apparent that a thorough and defensible literature search was not something you wanted to have to go back and re-do because you hadn’t been thorough, or you’d taken some shortcuts, or couldn’t organize the information, or your documentation was scribbles on any convenient piece of paper. The concept of a job done in a professional manner–one that your advisor couldn’t tear apart with a “Jones, I see you missed von Nibelung’s papers in 1902-4”–became instilled in me.

  26. Fluorine Chemist says:

    Derek, as usual, superbly articulated. I pretty much went through exactly what you have written during my graduate program in the early 1990s, at Iowa. The library was really good, and the librarian was a real gem, who was more than willing to lend a helping hand. I still remember when I had to give my first seminar during my second year – I had chosen Synthesis of Vitamin D, with Posner’s paper being my main reference. At that time, we had just gotten the online search functionality, and our librarian, Leo, stayed back till about 8:00 pm to get the search done. At that time, the online search costs were considerably cheaper after 6:00 pm. I still remember getting multiple cuts on my index finger after flipping through 100s of pages of journals! Thanks for the memories!!

  27. InfMP says:

    Speaking of wartime Angew. Chem., last year editor emeritus Peter Golitz did a presentation at ACS about the history of the journal and actually started crying when he covered the part where Nazi features were in the journal. I will never forget it.

    1. Wavefunction says:

      InfMP: I was there! Indeed a poignant moment. Golitz is a great guy and we had a drink later.

  28. Ted says:

    I started a summer internship at Reed in ’91, and none of my profs were around when I finally started lab work. I felt reasonably ambitious, and the first step of my synthesis required tethering few wayward glucose hydroxyl groups as isopropylidene moities. The procedure seemed straightforward and even ran overnight, but I was a little stymied by the ‘Dean Stark’ trap reference. None of my lab based texts seemed to have it, my fellow undergraduate aspiring organic chemists were unhelpful, and the only profs were of the PChem or Inorganic flavor.

    It ws hours in the stacks (Dean Stark? Stark, Dean? D. Stark?) before I finally tracked down the original E.W. Dean and D.D. Stark paper in the 1920 Journal of Industrial and Engineering Chemistry. I think I might have been at the brute force ‘every paper co-authored by a Stark’ stage. My victory was complete when I saw the handy dandy illustration – certainly worth 1000 words… I went traight back to lab and built one. Finally, back on track! Around the time I had it fired up, Randy, the stockroom manager, came by the lab and saw my setup. “That’s nice!” he said, continuing, “I’ve never seen anyone build their own…”

    Later that afternoon, I found a brand new, standard taper DS trap sitting on my desk. Still, no regrets!

    -t

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