Friday Fun: Google Scholar Surprises

From Google, a.k.a. the guys with all the data, comes the most recent Google Scholar metrics.

I'm starting to really enjoy the level of specificity Google's learned around academic sub-fields. For instance, in my own sub-field of organic chemistry, who knew that Green Chemistry and Molecules were rising so quickly through the ranks of top-cited publications?

The h5-index Google's using seems like a shot across the bow of the venerable Thomson Reuters Impact Factor. A glance through the top-cited papers across all of chemistry, couched in this 5-year zetigeist, shows some surprising trends in the field: tunable materials, solar conversion, nanoparticles, and genomic medicine win the day - nary a major total synthesis among the top-cited 'scripts of any journal I could find.

If you have a minute, play around - the Google site is clean, easy to navigate, and provides direct links to publications of interest. If you stumble across anything surprising, let me know in the comments!

Happy searching, Happy Friday!
See Arr Oh

Beautiful Chemistry: Hoye's HDDA + Napth Trap

Every so often, a reaction behaves so well that you just publish the crude NMR spectrum.

Professor Tom Hoye's HDDA* reaction, first reported in 2012, apparently fits the bill rather well, wouldn't you say?

From Org. Lett. 2015, ASAP.

Amazing - heat up a heavily conjugated triyne for 2 days, and it just does one thing, reproducibly and immaculately. I wonder whether Hoye and his group have any further tricks up their sleeve to try and control the diastereo  enantioselectivity of that sweet new quaternary center...time will tell.

--

*Please allow me touch of professional jealousy - this reaction opened up so many different questions for the Hoye group that they've published 10 manuscripts on it in just the last 3 years. Damn.

**Perhaps I've developed a love affair with barrelenes. Hmm.

Thanks for the catch, Per-Ola!

Friday Fun: Super-Calcium!

Super-Calcium
Source: Niggemann Group, RWTH Aachen

I like to stroll through journals on quiet mornings, over coffee. After a few months, you start to see trends crop up: The Gold Rush. Carbon-carbon bond cleaving chemistries. Fluorine and boron everywhere.

A new trend almost snuck in under my radar: Calcium catalysis. In the past, a few groups had played around with amino-ene reactions, arylated tertiary alcohols, and made some enantioselective calcium pincer complexes. But I couldn't honestly tell you that I had branded any specific group with the "calcium" label, as opposed to the "palladium" or "organocatalysis" badges worn by many.

Well, the Niggemann group in Aachen, Germany appears to want that distinction. Prof. Meike and her team have released a slew of interesting reactions - Friedel / Crafts, [3+2] cyclizations, cyclopropanations - with more popping up seemingly monthly. But...calcium? The stuff ingrained in our bodies, stapled in the phosphate matrix of our bones and teeth? The stuff I eat in yogurt, milk, and cheese is now a catalyst?

Source: Niggemann Group, RWTH Aachen

Let's dig a bit deeper. To start, Niggemann's group uses a weakly-coordinated calcium complex, calcium (II) bistriflimide. Next, they exchange anions with a quaternary ammonium source, producing the "mixed" catalyst Ca(II) PF6 NTf2, increasing organic solubility. The group claims that this complex exhibits both high selectivity for olefin coordination and stability against air and moisture - both important properties if you're exploring new reactions!

This new catalyst combo, dubbed "Super-Calcium" (with mascot, above), reacts like a wild hybrid of alumnium, gold, and palladium. It activates alcohols as leaving groups (Al). It permits [1,2] hydride shifts (Pd). It's a hard enough Lewis acid to unzip donor-acceptor cyclopropanes, but soft enough to permit hydroarylation (Al / Au). Checking some of the historical calcium-catalysis reactions (above) reveals even more head-scratching reactivity reminiscent of magnesium, titanium, or vanadium.

So, what's really going on here? First, I'd say it's early days: Some deuterium-labeling studies were done on the older reactions, and molecular modeling on this latest batch, but several steps (Vinyl cations? Hydride shifts?) make me wonder exactly how intimately the central calcium atom gets involved. Second, no one yet knows the exact structures of these reagents in solution; look how long it took to figure out LDA!!! Third, Meike's battle cry rings mostly true: reactions exploring the reactivity of early alkali metals (potassium? barium?) remain largely terra incognita.

More reactions will lead to more interest; perhaps a Calcium Craze looms over the horizon? Time will tell.

Happy Friday, Everyone!
-SAO

Another Wordle Challenge

Did you have fun playing the first Wordle chemist challenge?

I recall garnering some good-natured criticism, when I counted papers, for only including male chemists in the first go-'round. In the spirit of equality, here's three more Wordles for well-known female organic chemists!

Entry 6

Entry 7

Entry 8

Submit your answers in the comments!

Friday Fun - Superlative Publishers

Who's got the highest total # of published papers among living synthetic chemists?

Criteria: The person runs a group that makes things - sorry, no theorists this round - and works principally in some sub-field of synthetic chemistry (organic, organometallic, inorganic, photochem, med-chem, polymers, etc). 

I opened the discussion up on Twitter this morning, and used SciFinder, backed up with [cough] group websites that often need updating [cough]. 

Here's the list, as of 10:00 CST...

(All counts rounded to nearest 100 for convenience. SciFinder is an imperfect metric, since it includes abstracts and some duplicate entries. Please refer to caveats, below, for more detail.)

Alan Katritzky: 2,200 website; 2600 SciFinder

Source: exchangewire.com

Robert S. Langer: 2000 SciFinder

George Whitesides: 1,200 website; 1900 SciFinder

Leo Paquette: 1500 SciFinder

*E. J. Corey: 1,000 website; 1500 SciFinder

J. Fraser Stoddart: 1,000 website; 1400 SciFinder
Tobin J. Marks: 1,000 website, 1600 SciFinder
Paul v. Rague Schleyer: 1,300 website; 1600 SciFinder
Jean Frechet: 800 website; 1300 SciFinder
Irina Beletskaya: 1300 SciFinder

Barry Trost: 900 website; 1200 SciFinder

K.C. Nicolaou: 700 website; 1200 SciFinder

D. Reinhoudt: 1200 SciFinder

J. S. Yadav: 1,000 website; 1200 SciFinder

Ben Feringa: 1100 SciFinder
J-M. Lehn: 1100 SciFinder

E.W. "Bert" Meijer: 1000 SciFinder

Robert "Bob" Grubbs: 1000 SciFinder
Virgil Percec: 1000 SciFinder

Samuel "Sam" Danishefsky: 700 website; 1000 SciFinder

Ryoji Noyori: 800 SciFinder

Steven Ley: 900 SciFinder
Amos B. Smith: 900 SciFinder
James Tour: 500 website; 900 SciFinder
Stuart Scheiber: 500 website; 800 SciFinder
Karen Wooley: 700 SciFinder

Peter Langer: 700 SciFinder
Carolyn Bertozzi: 700 SciFinder
Jean'ne M. Shreeve: 500 website; 700 SciFinder
JoAnn Stubbe: 600 SciFinder

John Hartwig: 300 website; 600 SciFinder

K. Barry Sharpless: 600 SciFinder
Jacqueline Barton: 300 website; 600 SciFinder
Gautam Desiraju: 500 SciFinder
J.K.M. Sanders: 500 SciFinder

Ted Taylor: 500 SciFinder
Laura Kiessling: 400 SciFinder
M. Joullie: 400 SciFinder
Cynthia Burrows: 300 SciFinder
Melanie Sanford: 200 SciFinder

(Update: 1PM - Added Tobin Marks, Virgil Percec. 6PM - Added top-author women chemists. 7PM - Added Frechet, Desiraju, Sanders. 12AM 6/1 - Added Shreeve, Beletskaya)

Some caveats: I know it's folly to attempt correlating total publication count : scientific 'genius.'

If you only publish one paper, but you cure a major disease or invent a top-selling polymer additive, you're doing just fine! 

Also, I note that not everyone agrees that folks on this list belong in the "synthetic chemist" bucket - see ScienceGeist's (noted) exceptions here. (Update: P-O. Norrby noted another exception...)

Importantly, graduate students shouldn't feel down and out about this list. You can have a perfectly fine career with just a handful of papers; these superstars are the exception rather than the rule.

Curious thought: Publications in large synthetic groups certainly seem to follow a power law** - it takes ~15 years to get those first 100 papers, then about 8 for 100 more, and then the pace picks up dramatically. Presumably, this represents added hands and minds, along with building respect and excitement for one's work. I don't know how many other factors (prizes, location, grants, "buzz") are involved, but they probably belong to another post.

Readers, what say you? Have another person I've missed on the list?

*Who knew E.J. pwned ejcorey.com? (show of hands?) I think I smell a fantastic cyber-squatting campaign ...danishefsky.com, anyone?

**An example we discussed on Twitter: Phil Baran. It took him 15 yrs (1997-2011) to get 100 pubs. Next 25 or so have only taken 2 yrs. If power law holds, he'll have >400 pubs by age 50.

Can I Include My Wikipedia Page?

How often have you seen this old chestnut used when discussing hiring managers?

"They can't read, but they can certainly count."

Simple translation: When choosing between two similarly-qualified candidates, scuttlebutt suggests that the person with the most publications will advance to the next round of interviews. Of course, this begs another question...what counts as a "publication?"

Ask five scientists, and you'll get five different answers. Certainly, anything peer-reviewed merits inclusion. Ditto invited submissions, books, patents, reviews, or essays. But here's where the boundaries grow fuzzy. 

Can you include anything 'scholarly' on your CV to pad the stats?

[Insert embarrassing admission here]: I'm the guy who clicks on the "Show CV" link on faculty webpages. I find a strange (masochistic?) pleasure in comparing my career, such as it is, to those in similar age brackets or research areas. Certainly, these are folks who've played the game and won, so what do they choose to include? Here's a partial list: 

Abstracts
Publications "In press," "Accepted," "ASAP," "Proofs," "Submitted," "In Preparation"
Book Chapters
Conference Proceedings
Foreword / Introduction / Prologue
Afterword
Newspaper or magazine articles
Poetry
Plays
Book reviews
Perspectives
Research Summaries / Synopses
Blogs / Tweets / Comments

I'm sure I'm missing some; please suggest any others you've seen in the Comments section.

The simplest way to avoid any ethical boondoggles? Maintain separate lists of publications by type, or simply list "peer-reviewed" vs. "not." Will you be hired over the person who lumps 'em all together? 

Wish I knew.

R.I.P. Jerome Horwitz, Medicinal Chemist

Multiple news outlets (NYT, SciAm, Karmanos) now report the passing of Jerome Horwitz, 93, a career medicinal chemist behind AIDS drugs such as AZT (1964), stavudine (1966), and dideoxycytidine (1967). Most obituaries focus on two facets from his life:

1. His invention of AZT, a drug so synonymous with AIDS treatment that it's been mentioned in raps, novels, and Broadway shows.
2. His perceived failure to patent his antiviral molecules, thus "costing" him and Wayne State University millions in revenue realized instead by Burroughs Wellcome (later GSK). 

First report of AZT, J. Org. Chem. 1964, p. 2076*

I want to take a slightly different tack on Horwitz's career. For my money, he met all the criteria for a successful career in organic chemistry. He published >100 articles and book chapters; not a one-trick nucleoside pony, Horwitz's work covered sterols, acridines, tetrazoyl ylides, epoxide rearrangements, and analogue development of anticancer drug XK469. He had a fifty-year career as a professor at two universities. His work led to (at least) three approved drugs.

He even has a statue installed at Detroit Medical Center.

Even more interesting, he accomplished nearly everything in his career while staying in one place: Michigan. He jumped outside (briefly) to Illinois for a postdoc at Northwestern, but all other schooling and professional work came from in and around Detroit. It's amazing to me, given how much I and others have moved around for a career in science, that his tenure in one metro area lasted for a lifetime.

*Side note: When I look up old papers, I enjoy seeing who else I recognize among the authors in the same issue. 1964 must have been quite heady - in the same issue with AZT, we have papers by Nakanishi, H.C. Brown, Bill Dauben, Alfred Blomquist, and John Baldwin.

Keith Fagnou - Eternal Authorship

If you died tomorrow, would someone continue your work?
...even up to publication?

Prof. Keith Fagnou
Credit: U. of Ottawa

This thought gave me pause yesterday, as I browsed through journal contents and realized that Prof. Keith Fagnou, formerly of the University of Ottawa, was still publishing well into 2012.


For those unaware: Fagnou passed away unexpectedly in November 2009 after a short bout with H1N1 flu, only 38 years old. His research group, dubbed "The Fagnou Factory," kept coming to work, and kept publishing.


Between 2010-2012, despite Fagnou's death, he authored nearly 20 publications (and counting!). And these aren't retrospectives or reviews, but deep mechanistic and methodological studies, which landed in high-end places like Org. Syn., JACS, and Angewandte Chemie. 


So what's the secret to Fagnou's seemingly eternal success?


First, it pays to work in a "hot" scientific area. In the mid 2000's, C-H activation chemistry was booming, and KF was among the vanguard. From direct Pd-catalyzed arylations of pyridine N-oxides and alkylations of perfluoroaromatics, to Rh(III) cyclizations and explorations into -OPiv metal coordination, Fagnou's research had just begun to take off.


Second, his beloved "Factory" really seemed to love him back. Over his seven-year career at Ottawa, Fagnou mentored 4 postdocs, 24 graduate students, and 22 undergrads, many of whom would later stay on with him to pursue their doctoral degrees. After Keith's death, his group members organized a symposium in his honor, and even assembled a "Chuck Norris legends"-type tribute to him, in a mock JACS template.


I briefly met with Keith after a seminar, and he told us stories of his time as a schoolteacher and hilarious blooper-reel recaps of his time in the Canadian Navy. Everyone at the table felt his enthusiasm for chemistry (and life in general) really got him out of bed in the morning, and inspired others to do the same.


Here's to continued Keith's continued success; if I see an abstract in 2020, I'll hardly be surprised.


Update (2/15/12, 7:30) - Almost forgot this mini-review, published over at Chemistry Blog about a year ago. Derek's post on Keith generated an overwhelmingly supportive row of comments.