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To Synthetic Chemists: Research Ethics!


UBackwardsChemistry

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Tomas Hudlicky has gotten a bit of a reputation for writing about the seedy underbelly of organic syntheses. Derek Lowe summaries two of his more well known works in this vein:

http://pipeline.corante.com/archives/2012/11/01/hype_malpractice_and_scientific_misconduct_in_organic_synthesis.php

http://pipeline.corante.com/archives/2010/11/12/99_yield_that_friends_is_deception.php

Are these allegations true? Definitely; I've even been guilty of malpractice (error out of ignorance). It is important to be aware of the little shortcuts that we, as scientists, might not have otherwise thought twice about (eg reporting only the highest yield, NMR yields above 95% etc) and how they can really cheapen our contributions to chemistry. Please, when you start your graduate career this fall, think hard about how you can do chemistry in a legitimate, reproducable and honest way.

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I am pretty sure they are true. I'm not in any kind of postition to diss David MacMillan (haha), nor do I want to, or think he's guilty of any form of bad science at all (I don't think he is). But look at the hype that comes from his group for example - that's putting a pretty positive spin on things. 

 

Am I incorrect in saying that you can safely determine a single-diastereomer NMR yield over 95% (but not over some larger percentage whose exact value would depend on all kinds of things), but not a dr? With a large dr, you're comparing a big peak to a teeny one which is strongly affected by noise. With an NMR yield compared to an internal standard, you're comparing two 'big' peaks with similar, small, error due to noise. 

 

You can never *quite* be sure that an inorganic solid hasn't co-precipitated with your product, right?... (Well, you could, but does anyone go that far with every product they label with a yield?)

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Organic chemistry does get over-hyped a lot. 

My belief is that the problem comes from i. contraction of funding to universities (especially from industry) in the West ii. A greater weight being placed upon scientists to publish early and publish "high-impact". iii. More grad students & postdocs coming through the pipeline. These conditions mean that scientists who wish to secure financial backup have to "sell" their results a lot harder in the face of greater competition. 

 

I know a lot of chemists who talk disparagingly of "sellers" - I think a lot of chemists would naively like their research to be conducted and appraised as research for its own sake...that isn't a option in the world we live in. So I'm generally OK with the hype.

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Am I incorrect in saying that you can safely determine a single-diastereomer NMR yield over 95% (but not over some larger percentage whose exact value would depend on all kinds of things), but not a dr? With a large dr, you're comparing a big peak to a teeny one which is strongly affected by noise. With an NMR yield compared to an internal standard, you're comparing two 'big' peaks with similar, small, error due to noise. 

Good catch; however if you weigh out a spike (lets say 10 mg on a microgram balance) and then take the spectrum on a 300 you will probably lessen your certainty a bit. The user can also have a profound effect on this: I've also seen some specs that were shimmed like garbage integrated very generously to tell a good story...

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