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Derek Lowe The 2002 Model

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Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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June 10, 2009

Word For Word - But Why?

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Posted by Derek

I missed this a couple of months ago, but there was a paper withdrawn from the Journal of Organic Chemistry. The original is here, a contribution from the Indian Institute of Chemical Technology in Hyderabad on 2-aryl benzothiazoles.

The JOC editor's note is here, and states:

This manuscript was withdrawn from publication by the Editor-in-Chief of The Journal of Organic Chemistry. The basis for the withdrawal was a violation of the Ethical Guidelines to Publication of Chemical Research of the American Chemical Society. . .

The reason given is plagiarism from a paper in Angewandte Chemie in 2008, which is from Carsten Bolm's lab in Aachen on S-arylation of thiols. And here we find the trouble. Below are two sections - the first from the JOC paper, and the second from the original Ang. Chem.:

Among the various intramolecular reactions, S-arylation is comparatively less studied.(14) Two factors make this process difficult: First, thiols are prone to undergo oxidative S−S coupling reactions which result in the undesired formation of disulfides, and second, organic sulfur compounds can be effective metal binders, which leads to catalytic modification (or deactivation).(15) However, given the prevalence of C−S bonds in a wide range of pharmaceutically active compounds and polymeric materials,(16) it is desirable to find novel procedures that provide efficient access to such highly useful organic products.

Among the various cross-coupling types, S-arylation is comparatively less studied.[3] Two factors make this process difficult: First, thiols are prone to undergo oxidative SS coupling reactions, which result in the undesired formation of disulfides, and second, organic sulfur compounds can be effective metal binders, which leads to catalyst modification (or deactivation).[4] However, given the prevalence of CS bonds in a wide range of pharmaceutically active compounds and polymeric materials,[5] it is desirable to find novel catalytic procedures that provide efficient access to such highly useful organic products.

There's no doubt that this is a copy-and-paste job. And I believe that the ACS policy cited doesn't leave much wiggle room - if you do this, you get slapped down. What's silly about it is that it didn't have to happen. People borrow such background material all the time, to greater or lesser extents. But word for word? Bad idea. Frankly, if the Hyderabad authors had spent twenty minutes rewriting those sentences, no one would have ever noticed a thing. The automated similarity searches that can be done now (which I presume led to this incident) would have passed right over.

But (as far as I know) the conclusions of the JOC paper are still valid. And if you care about 2-arylbenzothiazoles, you might even want to see them. I note that the paper is still on the JOC web site, even though it's been "withdrawn". Is this the middle ground, then, a way to discipline people without yanking the results completely from the literature?

Comments (31) + TrackBacks (0) | Category: The Dark Side | The Scientific Literature


1. MedChem on June 10, 2009 12:41 PM writes...

So only the background information was plagiarized? Was the science still original though? I don't have access to the Angewandte Chemie paper.

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2. A-nony-muse on June 10, 2009 12:44 PM writes...

From my perspective, middle ground seems to be exactly the right place to land. Why should valid scientific data be withheld from the research community. As DL points out, the structural types described are of broad interest. On the other hand, the authors need to be taught a lesson regarding improper use of someone else's words. I dare anyone to run an automated similarity search on this post!

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3. Whateva on June 10, 2009 1:57 PM writes...

If they cut corners by plagiarizing the intro, who knows where else they cut corners? They obviously don't take pride in their work.

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4. Jan Teller Jr on June 10, 2009 3:11 PM writes...

I have to admit that it was quite unfortunate from the indian guys to basically copy and paste one paragraph from a previous paper in exactly the same topic.

I also think that they even choose not to reference Bolm´s work on the paper, which in fact seems something either quite moronic or very cheeky to do.

However, in substance, is it the methodology the same one? I dont see any iron-ish in the JOC´s paper?

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5. GC on June 10, 2009 3:22 PM writes...

Well since this is usually done to get their name "out there" and "be published" then there's no choice but to pull the paper. If you leave it out there, that tends to encourage more of the same.

Plus if their work ethic is this poor, then I sure as hell don't trust their science. It might have all been "done" sitting in front of a computer.

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6. Hap on June 10, 2009 3:37 PM writes...

No, the methods don't look anything alike. The Bose method constructs the benzothiazoles (all of which are 2-aryl), while the Bolm paper (which only makes 2-(arylthio)benzothiazoles) connects preformed benzothiazolethiols to aryl iodides. They have (almost) no overlap. (The Bose paper advertises its metal-free nature, as well - not a good fit with a metal-catalyzed thiolation.)

Why would you copy a paragraph of a paper with only tangential relevance to your own work? It's not like I understand copying someone's work or lying about your own, but this act seems to fail even a cursory risk-benefit analysis (particularly with the known existence of text-matching tools which make it much more likely that someone will find your text in juxtaposition with the one you copied from). There isn't much benefit to be gained, a lot (like your integrity and your job) to be risked, and a decent probability you'll be caught. Why do it?

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7. The Slimster on June 10, 2009 3:41 PM writes...

I wonder if this would have been discovered if it wasn't for the fact that Carsten Bolm (who authored the 2008 Angewandte paper) is an also an Associate Editor of JOC?

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8. Jan Teller Jr on June 10, 2009 3:54 PM writes...

I think I might have got that answer.

When you are in a top university with awesome weekly seminars or talks from leaders in the field, or you are a regular attending international meetings or symposia where you can talk to the elite in the subject, you know something more than your field, you get a lot to know how things work from the inside. You might also get to know which things are mandatory to do if you want to publish in top journals or sell your stuff to colleagues in order to build a reputation...

My impression is that in a place like Hyderabad, probably great in terms of human resources but a little far away from where things are happening, is hard to be an insider. Hence this guys understimated the importance of their "crime" and thought that they would get away.

I´d also like to add that writting a scientific paper originally for somebody whose mother tongue is not english can be horrific.

Imagine, if we have to learn Russian or Chinese to write a paper in 20 years time.

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9. Jan Teller Jr on June 10, 2009 3:58 PM writes...

Ask D.W about K.A writting skills

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10. Curious Wavefunction on June 10, 2009 5:14 PM writes...

This is just plain weird. It's not even like they would stand to benefit in any big way from copying that paragraph. My interpretation is simply that the authors innocently saw no harm in doing this. Which is even more concerning and goes to show that ethics workshops should be mandatory at these places.

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11. aytchtewoh on June 10, 2009 9:55 PM writes...

This is small potatoes. There was a guy who plagiarized entire sections of the Merck Index for his own "encyclopedia"...

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12. Andy on June 11, 2009 3:57 AM writes...

If the paper has been withdrawn prior to publication, but is still available, then I might want to use the chemistry therein as there doesn't seem to be any suggestion that it is invalid. With no page number, how would I cite it? I could cite it as an ASAP article, but will it just remain as an ASAP article forever? What if it disappears?

#8 "Hence this guys understimated the importance of their "crime" and thought that they would get away.

I´d also like to add that writting a scientific paper originally for somebody whose mother tongue is not english can be horrific."

This may well be a reason - perhaps also the person writing the paper, or at least a draft containing the offending paragraph, was the student, and thought it would be ok to steal an introductory paragraph, and the boss didn't notice.

Is this in any way similar to sampling in music?

Is there also not a law that says certain amounts of material may be lifted in certain situations? (fair use?). It's fair to say I don't know what I'm talking about, though.

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13. Big Bob on June 11, 2009 4:11 AM writes...

This probably happens more then we realise in the literature. From my experience of seeing first drafts of PhD theses from indian/chinese students huge pieces are copied direct from papers. This isn't an attempts at cheating, it's a cultural thing, something which is as difficult for me to understand as it is to them to understand why it's wrong.
One question for you now, what would I do if I wanted to cite a paper that had been withdrawn, such as this one, I couldn't not cite it if my work was in some way related, the fact that it is still accessible at present means that the whole withdrawal process is meaningless. I completely agree that this is valuable research and shouldn't be removed from the public domain, maybe in cases such as this the authors should be given the opportunity to replace the offending parts or have them deleted from the pdfs available for the paper.

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14. Smoki on June 11, 2009 5:41 AM writes...

I also think that the copying of the paragraph might be connected with the struggle of writing the paper in English. I believe from my first-hand experience that copying parts of other articles might be a fairly common practice in many non-English speaking countries. But typically it would involve plagiarizing a large number of papers, taking one sentence from this, another from that article and so on, meshing everything together. In this way, the misdemeanor is not as obvious, it is harder to detect and less likely to offend the authors of previous papers.

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15. MTK on June 11, 2009 7:26 AM writes...


You would cite it by its DOI #.

I'm going to cut these guys some slack. There certainly seems to be no intent to deceive or take credit where credit is not due.

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16. Andy on June 11, 2009 7:42 AM writes...


Does that mean then that it is going to remain 'withdrawn but available' (I suppose that happened when printed papers were later retracted in the past) in a sort of chemical purgatory? It hasn't actually been published in an issue, which is the difference from printed retractions. Are they free to publish it somewhere else? If the paper is going to be removed at some point, the DOI would be meaningless.

I think most people agree with you - the problem is that JOC doesn't.

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17. g on June 11, 2009 8:05 AM writes...

If there were some cheating/plagiarism "middle ground", things would get too complicated and political connections could help high-profile labs avoid full consequences. There needs to be strict consequences for cheating/plagiarism no matter the magnitude, which could be argued and influenced.

Totally withdraw the paper. If this is truely novel and important information, that lab, and probably some others, will try to repeat it and get it published in a lesser journal.

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18. cookingwithsolvents on June 11, 2009 8:58 AM writes...

I would probably reference person X, person Y "unpublished results" with a DOI. . .

Weird kind of limbo for a scientific result. I do believe that it's a misdemeanor but still a crime to plagiarize intro paragraphs.

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19. Anonymous on June 11, 2009 9:03 AM writes...

If a paper is withdrawn, would the authors be able to resubmit with the offending sections corrected?

I guess with the new blast tools available for comparing texts, this sort of thing could be sorted out prior to publication in the future.

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20. Chemjobber on June 11, 2009 9:04 AM writes...

Once I was editing the paper of a Chinese student and he had lifted a lovely passage of text from the literature. When I pointed it out to him, he replaced the lifted passage with another lifted passage from the literature! The funniest part is when you have a paper that's written in broken English and then there's a passage that's clear as day -- what changed?

Ultimately, though, I agree with Big Bob. It's cultural and is likely changing over time to standards closer to our own.

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21. Nick K on June 11, 2009 9:13 AM writes...

This is rather reminiscent of the Paquette scandal of a few years ago: the plagiarism was not in the chemistry (which was original and good) but rather in the introductory text. Most strange and difficult to understand. Big Bob is quite right when he says Indian and Chinese workers are prone to this kind of plagiarism. An Indian grad student I knew essentially wrote the introduction to her thesis by copying out the texts of literature papers.

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22. RTW on June 11, 2009 10:16 AM writes...

In many instances just because an article has been withdrawn it does not remove it from circulation. Lets take some other examples from Nature and Science for example.

Using CAS Search or other online tools the withdrawn article will more than likely still be in the database systems without flags indicating it was withdrawn.

Additionally people that subscribe to print versions, its not like those pages magically disappear, or are removed from peoples file cabinets if they photocopied it because it was relevant to their research 3 years ago. They may not ever notice the published withdrawal or published corrections.

Has anyone wondered how this is all handled electronically via citations. Not everyone can afford access to journal papers online, to get the corrected versions. I might be able to afford to do a search but need to use my print copies... How does one determine a print or photocopied article has been corrected or withdrawn?

I use to have electrinic access to all the relavant journals when I was with Big Pharma. Now that I am not a member of such a large organization anymore I have to rely on print at the local library or my own personal subscriptions which are getting hard to afford.

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23. LLJ on June 11, 2009 10:41 AM writes...

During my recently completed Ph.D. I tried to repeat some reactions reported by Bose and Idrees in the articles: (a) Synthesis 2007, 6, 819-823; (b) J. Het. Chem. 2007, 48, 667-672; and (c) J. Org. Chem. 2006, 71, 8261-8263. The reported reaction conditions did not give the reported products, but led only to degradation of the starting material. Bose never replied to my, nor my supervisor's, e-mail inquiries as to how we could properly obtain the desired products using the reported methods.

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24. SpanishNativeSpeaker on June 11, 2009 12:56 PM writes...

I understand the reason behind the copy-and-paste of an introductory paragraph. However, not citing the source is a no-no, even if the methods developed are not related.
And about Jan Teller Jr's #8 comment:"I´d also like to add that writting a scientific paper originally for somebody whose mother tongue is not english can be horrific". You are right, it is horrific and you spend a lot extra time trying not to sound like the background papers that you have read.
I envy the people who can write with the ease and eloquence that Derek and other frequent posters here write
(I just spent 45 min writing this, I need to go back to real work!!)

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25. DC on June 12, 2009 4:08 AM writes...

Has anyone noticed that the quality of English expression in papers from Chinese groups have risen dramatically. One Chinese prof told me that papers would be sent to an American firm specializing in proof-reading texts to get the English up to scratch. Pretty good!

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26. Anonymous BMS Researcher on June 12, 2009 3:16 PM writes...

One tool that has been used to spot potential plagiarism is:

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27. Kate Ebneter on June 12, 2009 7:05 PM writes...

While I suspect that the authors' being "non-native speaker(s) of English" may play some role in this, it happens in other cases, too, where it's clearly just sheer laziness. Back when I was an astronomer, I noted another's Ph.D. dissertation and the published paper derived from it that lifted several paragraphs nearly word-for-word from my first published paper, which was a review article about the same object. Reading the dissertation's introductory section was kind of a deja vu experience.

I didn't do anything about it; perhaps I should have, I don't know.

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28. ss on June 13, 2009 12:10 AM writes...

I think this practice of minor plagiarism is only the tip of the iceberg, the iceberg being more serious infractions, "boosting" reaction yields, (70% instead of the actual 40% etc.), including some "additional substrates" in the list of successful substrates, those that have not been subjected to the reaction conditions, or those that have and dont work, or even more serious ones cooking up the whole paper.

I have first hand experience of having watched these happen and also a lot of "hearsay" evidence of this happening in several Indian research labs and universities.In fact that was one of the main reasons why I did not want to do my Phd in India. These problems are widespread but no action has been initiated to clean up this mess. The main reason is the lack of administrative will,lethargy, lack of guts or basically an attitude of CYA or not wanting to wash dirty linen in public.

I think the only way to correct this is for reputed journals to blacklist the whole institution from which such a paper emanates till the concerned guilty person has been suitably punished.

And as no.10 mentioned mandatory ethics workshops may also help.

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29. spsp on June 15, 2009 3:46 AM writes...

Please don't complain about non-native speakers of English when you means "people from India, China, or other less developed countries". Europeans do proofread their papers. The difference is cultural: in the West, authors know that broken English is simply not acceptable in scientific papers. Indians, on the other hand, constantly make irritating and inexcusable mistakes, like frequent typos in common words.

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30. spsp on June 15, 2009 3:51 AM writes...

D'oh. "When you means". ... Sneaky little hobbitses messes up our spellings, Preciousss ...

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31. Dan on June 26, 2009 12:12 PM writes...

I am afraid that some of the comments here will confuse people, so as someone with editorial experience I wanted to make two points clear. First, the passage quoted would be plagiarism whether or not the paper it was taken from is referenced. The only way that such a passage would not be plagiarism is if the passage were put into quotation marks. If you put your name at the top of a paper, you are saying that you wrote the paper. If it is someone else's words, you did not write the paper and the authorship is a lie. Whatever the reasons or excuses, plagiarism cannot be tolerated.

Second, the penalties for plagiarism at journals go beyond withdrawing the paper and typically start at a multi-year ban on publishing with the journal. It should also be recognized that plagiarism is easy to catch once it is suspected; you just google a unique-looking phrase.

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