Move On Along to Colorblind Chemistry for more Bumper Cars!

This is just to say

I have allowed
Dr. Marshall
to take over
this column

and which
you were probably
clicking
for updates

Forgive me
they needed a home
he has time
I have less

With apologies and kudos to both William Carlos Williams and Chemjobber, who enjoys adapting it from time to time.

Chemistry Bumper Cars, 2018

Multiple anonymous internet comments agree: Faculty moves still occur with rapidity and fluidity. Think of them like a "jobs plasma," flowing around major campuses every few years.

The 2017 list had grown like a wild blackberry bramble, so it needed a trim. If you hear of an impending 2018 move, please tell me in the comments, and I'll post in the "Pending Confirmation" section. Escape from this purgatory involves sending me a link or other documentation from the new institution. Happy speculating!

Moves

Nozomi Ando (Princeton to Cornell)  two sources
Alan Aspuru-Guzik (Harvard to Toronto)  three sources
Yimon Aye (Cornell to EPFL)
Mark Banaszak Holl (Michigan to Monash)
Christoph Bostedt (Northwestern to EPFL)
Kenneth Brown (Georgia Tech to Duke ECE)
Tim Cernak (Merck to Michigan)
Philip Cole (JHU to Harvard)
Qiang Cui (Wisconsin to BU)
Tanja Cuk (Berkeley to UC Boulder)
Li Deng (Brandeis to Westlake Inst, China)
Eilaf Egap (Emory to Rice)
Aaron Esser-Kahn (UCI to Chicago)
Fabien Gagosz (CNRS to Ottawa)
Sharon Hammes-Schiffer (UIUC to Yale)
Eva Harth (Vanderbilt to Houston)
Jen Heemstra (Utah to Emory) 
Ryan Hili (UGA to York)
Rong Huang (VCU to Purdue)  
Kami Hull (UIUC to UT Austin)
Tristan Lambert (Columbia to Cornell) 
Jared Lewis (Chicago to Indiana)
Fu-Sen Liang (UNM to CWRU)
Michael McGehee (Stanford to UC Boulder)
Brian McNaughton (CSU to Delaware)
Christian Melander (NC State to Notre Dame)
Pere Miro (UNF to South Dakota)  
Garrett Miyake (UC Boulder to Colorado State) 
Bill Morandi (Max Planck to ETH)
Peter Nemes (GWU to UMD - College Park)
Jens Norskov (Stanford to DTU)
Hien Nguyen (Iowa to Wayne State)
Rob Paton (Oxford to Colorado State)  
Christine Payne (Georgia Tech to Duke ME)
Poul Petersen (Cornell to RUB)
Scott Phillips (PSU to Boise State) 
Jen Pokorski (CWRU to UCSD)
Mario Rivera (Kansas to LSU)
Michael Rubenstein (UNC to Duke)
Jayaraman Sivaguru (North Dakota to BGSU)
Christine Thomas (Brandeis to Ohio State)
Bill Tolman (Minnesota to Washington U St. Louis)  thanks, Chemjobber and Bill!
Jeff Van Humbeck (MIT to Calgary)
Greg Verdine (Fog or LifeMine)
David Walt (Tufts to Wyss Institute) 
Ryan White (UMBC to Cincinnati) 
Elizabeth Young (Amherst to Lehigh)
Junrong Zheng (Rice to Peking) 

Pending Confirmation

Karena Chapman (Argonne to Stony Brook)
Ming Hammond (Berkeley to Utah)
Tom Mallouk (PSU to Penn)
Douglas Philip (St. Andrews to Northwestern)  two sources
Ian Webb (PNNL to IUPUI)

OK, it's an imperfect employment metaphor, but stellar profs *are* like mutant superheroes....right?

New Hires

Netz Arroyo (JHU)
Bram Axelrod (Purdue)
Keriann Backus (UCLA Biochem)
Buz Barstow (Cornell)
Kwabena Bediako (Berkeley)
Elizabeth Bess (UCI)
Ambika Bhagi-Damodaran (Minnesota)
Aaron Bloomfield (Duquesne)
Zarko Boskovic (Kansas)
Jennifer Bridwell-Rabb (Michigan)
Carl Brozek (Oregon)
Carson Bruns (UC Boulder)
Jonathon Caranto (Central FL)
Amanda Cook (Oregon)
Luke Davis (Tufts)
Selvan Demir (MSU)
Megan Fieser (USC)
Joseph Fournier (Wash U St. Louis)
Stephen Fried (JHU)
Rebecca Gieseking (Brandeis)
Robert Gilliard (UVA)
Grace Han (Brandeis)
Hee-Sun Han (Illinois)
Scott Hansen (Oregon)
Jordan Harshman (Auburn)
Dugan Hayes (URI)
Mark Hedglin (Penn State)
Shabnam Hematian (UNCG)
Raul Hernandez Sanchez (Pitt)
Glen Hocky (NYU)
Scott Horowitz (University of Denver)
Ashlee Howarth (Concordia)
Ying Hu (UIC)
Tao Huan (UBC)
Michael Inkpen (USC)
Jiangbing Jiang (Cincinnatti)
Tim Johnstone (UCSC)
Rashad Karimov (Auburn)
Christopher Kelly (VCU)
Sarah King (Chicago)
Lydia Kisley (CWRU)
Abigail Knight (UNC Chapel Hill)
Joshua Kogot (Miss State)
Kevin Kou (UC Riverside)
Mike Larsen (Western Washington)
Steven Lopez (Northeastern)
Marek Majewski (Concordia)
Lara Malins (ANU)
Amanda Manhart (Temple)
Jeff Martell (Wisconsin)
Jarad Mason (Harvard)
Jesse McDaniel (Georgia Tech)
Quentin Michaudel (Texas A+M)
Jeff Mighion (Kent State)
Phillip Milner (Cornell)
Thomas Montgomery (Duquesne)
Shuming Nie (UIUC)
Lea Nienhaus (FSU)
Lisa Olshansky (UIUC)
Zachariah Page (UT Austin)
Malay Patra (TIFR)  
Amanda Patrick (Miss State)
Shauna Paradine (Rochester)
Joe Patterson (UCI)
Nicholas Race (Minnesota)
Monika Raj (Auburn)
Lindsay Repka (Middlebury)
Jon Rittle (Berkeley)
Anthony Rojas (Salisbury)
Sudeshna Roy (Ole Miss)
Michael Ruggiero (UVM)
Tomce Runcevski (SMU)
Joel Smith (FSU)
Rachel Steinhardt (Syracuse)
Troy Stich (Wake Forest)
Alexandra Strom (Smith)  two sources
John Swierk (Binghamton)
Sesha Vempati (IIT Bhilai)
Bess Vlaisavljevich (South Dakota) 
Wenjing Wang (Michigan)
Alison Wendlandt (MIT)
Sidney Wilkerson-Hill (UNC)
Xin Yan (Texas A+M)
Elizabeth Young (Lehigh)
Ran Zhao (Alberta)


Pending Confirmation

Robert Comito (Houston)
Scott Cushing (Caltech)
Ryan Hadt (Caltech)
Neel Shah (Columbia)


--

For 2017 moves, click here
For 2016 moves, click here
For 2015 moves, click here
For 2014 moves, click here.
For 2012-2013 moves, click here. 

Conference Talks, Great Success!

'Tis the Season for stitching up the last year of your life, making a few key graphics, and tossing them into a (presumably) 30-minute talk to inform and entertain your colleagues. That's right, Summer Seminar Vacation!

But wait - will your message come through? Will I, as an informed audience member, walk out of the auditorium singing your praises, or desperately fighting off Morpheus?

I'd rather watch this grow all day than listen to certain speakers again...

Without further ado, I'd like to capture some honest feedback, both given and received, that I'll call the "Summer Talk Axioms." Certainly, nothing is new under the sun: I tread in tracks left by Derek, Chemjobber, Fabian, ChemBark, and many other sage counselors. I question only that, given these many posts (and more sure to come), how has the message has not percolated into the community faster? 

Anyway, to the meat of it:

• Help me learn: What are the big takeaways? Why did you do them, and how? If you were forced to deliver this same talk in 2 minutes, could you do it, while maintaining understanding in your listener? That's a tough benchmark!

• Timing: For the love of all that is holy, please do not attempt to deliver a 50-minute "pre-fab" slide deck inside of 30 minutes. Ditto a 30-minute deck inside a 15-minute lightning talk. If you are switching slides every 20 seconds, it's nigh impossible for your poor audience to keep up...

• Engagement: Stop every few minutes to look someone in the eye. Tell a joke. Modulate your voice. Take a drink of water to let a point sink in. Presentation skills belong to that witches' brew of soft skills and social norms blended with (some) content. Often, we listeners engage more with the person and their body language in place of the content.

• Tell a story. One. Not multiple vignettes of seemingly unrelated threads. Present a logical whole.

• Don't repeat "this is exciting!" If you have to reinforce this, your content almost surely isn't.

• Know your time, and practice delivery. As a hint, you're probably over time when the audience begins to check their phones. Or mutters. Leaves for cigarette and bathroom breaks. A good talk has a clear beginning, middle, and end, and has distinct landmarks for major points and applause / recognition. Know yours.

• Proofread. Ask someone who loves you to proofread. Ask someone who hates you to proofread. Proofread. Proofread. Especially embarrassing - misspelled titles!

• The four "Thank-Yous" - Thank your host for introducing you. Thank the organizers / school / company for the opportunity to visit. Thank your group, coworkers, or boss for their collegiality. And thank the audience for listening. This goes a very, very long way.

• Answer questions succinctly. Two or three sentences, and a promise to follow up after the talk, should be sufficient. Anything more holds the other 99% of your audience captive, while you dig through back-up slides and comment about long-departed group members. 

Your talk was nice. Very nice. Great success!

Readers, I'm sure I've missed some, and welcome any input in the comments. 

Happy Summer!

Help Wanted: C&EN Audience Engagement Editor

Hello, intrepid readers. Hope those of you living above the Tropic of Cancer are enjoying the start of Summer.

Though this usually falls into the Chemjobber camp, an inside source asks whether I can recommend an engaged, excited, passionate web-denizen for a newly-created role at the newsmagazine. From the horse's mouth (emphasis mine):

"We're hiring for someone to act as the 'voice of the magazine' on our social accounts, writing our newsletters, and helping us shape overall social and engagement strategies. Important would be to have someone who is comfortable with social and loves chemistry."

Wow, that sounds like the exact job I would have wanted coming out of grad school! However, I can't keep pace with the ever-changing landscape of social media* and iPhone apps. It's best left to someone, methinks, with an "always-on" mentality and a quicker set of thumbs than yours truly.

If you or someone you know are interested, please apply here.
Look forward to crossing paths with you in the Great Social Experiment.

--
*Get off my lawn, you kids with yer Tencent and Snapchat and Baidu and Twitterz and Hipstergram and Skype and Facebook and Yelp and hi5 and Qzone and Friendster!

Chemistry Bumper Cars, 2017

In the age of globalization, Reddit, DM, and coffee shops, it's surprising when you don't hear about a faculty move at least two months ahead of it becoming reality.

(Alert! Repurposed text to follow!)

Last year's list has grown ungainly, and so it's time for a new batch. Same rules apply: If you hear of a move, please tell me in the comments, and I'll post in the "Pending Confirmation" section. Escape from pending purgatory involves sending me a link or other documentation from the new institution. Happy speculating!

Update, May 2017: Are you a newly-minted prof? The stalwart reporting cadre of C&EN want to make you aware of a (private, exclusive) Facebook group to share stories and support your new role. Want in? Go here.

Moves

Huiwang Ai (UC Riverside to UVA)
Adam Braunschweig (Miami to CUNY)
Brian Blagg (Kansas to Notre Dame)  five sources
Gong Chen (PSU to Nankai, 2016)
Qiang Cui (Wisconsin to Boston U)  thanks, SJE!
Mark Davis (Caltech to USC)  thanks, Maxxie!
Michael Fischbach (UCSF to Stanford ChEM-H)  thanks, Carolyn!
Nathan Gianneschi (UCSD to Northwestern)
Karen Goldberg (Washington to Penn)
Jim Heath (Caltech to ISB, admin)
Ryan Hili (UGA to York)
Yannis Kevrekidis (Princeton to Johns Hopkins)
Laura Kiessling (Wisconsin to MIT)
Ken Knappenberger (Florida State to PSU)
Kirill Kovnir (Iowa State)
Chenglong Li (OSU to Florida)
John MacMillan (UTSW to UCSC)
Christopher McCurdy (Mississippi to Florida)  thanks, Cunningham!
Pere Miro (UNF to South Dakota) thanks, Chemjobber!
Randall Peterson (Harvard MGH to Utah, admin)
Ronald Raines (Wisconsin to MIT)
Chris Scarborough (Emory to Syngenta)
Kirk Schanze (Florida to UT-San Antonio)
Daniel Seidel (Rutgers to Florida)
James Skinner (Wisconsin to Chicago)
Carlos Silva (Montreal to Georgia Tech)
Stavroula Sofou (Rutgers to Johns Hopkins)
Christine Thomas (Brandeis to Ohio State)
Greg Verdine (WaVe, WuXi Venture, Eleven, Fog)
Casey Wade (Brandeis to Ohio State)
Daniel Weix (Rochester to Wisconsin)
Michael Wolfe (Harvard Med to Kansas)
Roy Wollman (UCSD to UCLA)
Bill Wuest (Temple to Emory)
Chengguo Xing (Minnesota to Florida)  one source


Pending Confirmation

Aaron Esser-Kahn (UCI to Chicago) two sources
Jen Heemstra (Utah to Emory?) three sources
Rong Huang (VCU to Purdue?)  one source
Andreas Lendlein (HZG to Texas A+M?)  two sources
Rob Paton (Oxford to Colorado State?)  one source
Scott Phillips (PSU to Boise State?) one source
Jennifer Prescher (UCI to Minnesota)  one source
J. Fraser Stoddart (NW to Texas A&M?) conflicting sources...
David Walt (Tufts to HMS?)  one source
Junrong Zheng (Rice to Peking?)  one source

Very unlikely method - too much H2O gets into the deuterium oxide...

New Hires

Samuel Awuah (Kentucky)   thanks, Lippard lab!
Jean-Luc Ayitou (Illinois Institute of Tech)
Jeff Bandar (Colorado State)
Chris Barile (UN-Reno)
Eszter Boros (Stony Brook)
Carson Bruns (CU Boulder) thanks, Carson ?!?!
Andrew Buller (Wisconsin)  thanks, Chemjobber!
Justin Caram (UCLA)
Carlos Carrero (Auburn)  three sources
Matthew Chambers (LSU)
Craig Chapman (UNH)
Xi Chen (CUNY ASRC)
Saurabh Chitnis (Dalhousie, 2018)
Christopher Dares (FIU)  two sources
Laura Dassama (Stanford Chem-H)
Eric Detsi (UPenn)
Todd Doran (UMN)
Letian Dou (Purdue)
Elizabeth Elacqua (PSU)
Noemie Elgrishi (LSU)
Shirin Faraji (Gronigen)
Jeremy Feldblyum (SUNY Albany)
Thomas Gianetti (Arizona)
Todd Gingrich (Northwestern)
Samer Gozem (Georgia State)
Marie Heffern (UC Davis)
Christopher Hendon (Oregon)
Kristin Hutchins (Texas Tech)  thanks, Moore group!
Enver Izgu (Rutgers)
Meredith Jackrel (WU St. Louis)
Carlos Jimenez-Hoyos (Wesleyan)
Tim Johnstone (UCSC)
Matt Jones (Rice)
Evan Joslin (U of the South)  one source
Masha Kamenetska (Boston U)
Jessica Kramer (Utah Bioengineering)
Jiwoong Lee (Copenhagen)
Semin Lee (LSU)
Mark Lipke (Rutgers)
Ashley Longstreet (Tampa)   two sources
Justin Lopchuk (Moffitt)
Long Luo (Wayne State)
Tomoyasu Mani (UConn)
Megan Matthews (Penn)
Jamie Neely (Saint Louis U)  thanks, Paul!
Andrew Nieuwkoop (Rutgers)
Michael Norris (Richmond)  one source
Davit Potoyan (Iowa State)
Eric Price (Saskatchewan)
Rebecca Quardokus (UConn)
Madalyn Radlauer (San Jose State)  personal communication
Maxwell Robb (Caltech)
Andrew Roberts (Utah)
Jennifer Rupp (MIT)
Aaron Rury (Wayne State) from school Facebook page (?!?)
Brett Savoie (Purdue ChemE)
Kimberly See (Caltech)
Christo Sevov (Ohio State) thanks, Sanford Lab!
Benjamin Sherman (TCU)  two sources
James Shepherd (Iowa)
Alexey Silakov (Penn State)
Zachary Smith (MIT)
Alexander Sokolov (Ohio State)
Jamie Spangler (Johns Hopkins)
Mark Tibbitt (ETH)  one source
Pratyush Tiwary (Maryland)
Emily Tsui (Notre Dame)
Gael Ung (UConn)
Alexandra Velian (Washington)
Konstantinos Vogiatzis (Tennessee) one source
Yiming Wang (Pitt)  in department phone list
Zachary Wickens (Wisconsin)
Jingjie Wu (Cincinnatti)
Han Xiao (Rice)
Xingchen Ye (IUB)
Joseph Zadrozny (Colorado State)
Julia Zaikina (Iowa State)
Melissa Zastrow (Houston)
Jianyuan (Jason) Zhang (Rutgers)

Pending Confirmation

Jennifer Bridwell-Rabb (Michigan)
Scott Hansen (Oregon)
Dugan Hayes (URI)
Scott Horowitz (UC-Denver)
Rashad Karimov (Auburn)
Stephen Lopez (Northeastern)
Lara Malins (ANU)
Jarad Mason (Harvard)
Jeff Mighion (Kent State)
Jia Niu (Boston College)
Sudeshna Roy (Ole Miss)
Bess Vlaisavljevich (South Dakota)
Ran Zhao (Alberta)

--

For 2016 moves, click here
For 2015-2016 moves, click here

For 2014-2015 moves, click here.
For 2012-2013 moves, click here. 

Better Than Word of Mouth

Hello, dear readers. It's been...a while. I promise the blog is not dead, just sleeping for now. My 2017 New Year's resolutions include sculpting specific time out for all the sci-writing goodness. Stay tuned.

Enough maudlin overtures. Now, on to the fun!

Strem has, as any synthetic guru would attest, the highest-quality metal precursors in the biz.* Now, you could spend a weekend cracking ampoules to find out, or just open to the Supporting Information of one of Jeff Bode's recent publications in Org. Lett. Perhaps you remember this reaction - SnAP synthesis of saturated heterocycles - best from a cheeky Derek Lowe tweet:

That's in reference to the stoichiometric incorporation of tin** in the reagent, which serves as a linchpin for the eventual transmetalation to a copper species and ring closure, neatly without disturbance of the ipso heteroatomic group.

Well, much to my surprise, Prof. Bode has climbed on the recent trend of showing one's work through tactful inclusion of smartphone pics to buoy up procedure adoption. Especially with fussy transition metals, valency, contaminants, poor environment, and a whole host of other factors lead to catalyst poisoning and color changes. In the SnAP case, the litmus test seems to be formation of a correctly ligated Cu(II) ion in lutidine relative to the (probable) hexaaquo cuprate species formed as a blue heterogeneous train wreck.

The kicker? The fairly indiscreet preference for the Strem copper(II) precursor over all other suppliers. Look at the change! Night and day, and key to making these reactions work.

You couldn't buy better advertising than this....right, Strem?
Bravo, Bode group! I look forward to seeing your colorful coupling chemistry in future reads.

--

*Dear Strem: please send non-sequential $50 bills to See Arr Oh at Big City Company, USA
**SnAP. Get it? [drum kit]

A Tale by Mail

Long-time readers will no doubt be aware of my running affectation with the "Profiles, Pathways, and Dreams" series of books from ACS; books which, had I not read them in grad school, would probably cause this blog to never exist.

So I have a sneaky hobby: scouring the Internet's used book counter to assemble an entire set. Thus far, I've collected 17 of the 22 from the original 1990-1995 run. As I'm simultaneously trying for thrift, I'm proud to say the most I've paid for one of these books was around $25.

One of the best came in the mail only today - a first-edition, basically mint copy of Djerassi's Steroids Made it Possible. You know, the one with the picture of Nobelist R.B. Woodward going Mike Tyson's Punch-Out! on another esteemed chemist?

Steroids Made it Possible, ACS Books, p. 60

I open the plastic packaging, breathe in the old-book-paper smell.  But wait, there's no library markings. And the book is, what, 26 years old, and is basically undamaged? Curiously, I opened the cover, and realized that Djerassi himself had dedicated it:

To whom, exactly? Why, to Larry Lehmkuhl, the previous president of St. Jude Medical, according to Bloomberg. And is that really Carl's signature? I've compared it against two *for sale* on eBay and at Amazon - $89 euro and $39.85, as of this writing, respectively - it's the real McCoy.

This, of course, raises more questions: Did Lehmkuhl ever read his gift? Was he from a chemistry background? (I can't find much about him through the usual channels).

Did Djerassi mail out copies of his books, en masse, to anyone interested? If so, perhaps other signed treasures are out there, waiting to be found.

ETC: Vonnegut, Djerassi, and a Mystery Polymer

I've recently finished the 1973 novel Breakfast of Champions, by acclaimed science fiction / humor writer Kurt Vonnegut. For those unfamiliar with Vonnegut's work, I enjoy drawing parallels* between him and "chemical provocateur" Carl Djerassi.

These two men share some odd similarities: born within 13 months of one another, each man suffered the Second World War - Djerassi as a refugee; Vonnegut as a POW - and had their personal lives scarred by young, tragic deaths in their families. Nevertheless, both became prolific writers of short stories, novels, and plays, and both lived to be elder statesmen in their chosen careers: Vonnegut to 85, and Djerassi to 91.

I'd even wager that they looked somewhat alike, with their bushy mustaches, well-coiffed hair, stylish clothing and impish eyes:

Novelist Kurt Vonnegut
Credit: Enotes

Chemist and writer Carl Djerassi
Credit: DLD / Stanford

Breakfast of Champions convinced me that Vonnegut may have had more than a passing fancy for chemistry, himself. Consider this hand-drawn rendering of a mystery plastic, ostensibly factory run-off that main character Kilgore Trout has unfortunately found stuck to his feet after wading through a river in Midland City, Michigan:

Credit: Kurt Vonnegut, Breakfast of Champions

Clearly, that's a cyanoacrylate co-polymer - think Superglue - and it seems to be drawn with a dendrimeric A-B-A architecture. I'm guessing that the ethylene glycol spacers (O-CH2-CH2-O) are meant to suggest the foaminess several characters encounter in the novel, that this mystery polymer is "...the stuff f***ing up Sacred Miracle Cave...", an in-book tourist trap overrun by large, odorous brown bubbles.

Incidentally, I love Vonnegut's inference for the continued polymer chain; where we chemists might write n, Vonnegut inserts his time-work "ETC."

Why? I'll let the author explain his philosophy:

"The man who taught me how to diagram a segment of a molecule of plastic was Professor Walter H. Stockmayer of Dartmouth College. He is a distinguished physical chemist, and an amusing and useful friend of mine. I did not make him up. I would like to be Professor Walter H. Stockmayer. He is a brilliant pianist. He skis like a dream.

 And when he sketched a plausible molecule, he indicated points where it would go on and on just as I have indicated them - with an abbreviation that means sameness without end.

 The proper ending for and story about people it seems to me, since life is now a polymer in which the Earth is wrapped so tightly, should be that same abbreviation . . .it is in order to acknowledge the continuity of that polymer that I begin so many sentences with 'And' and 'So,' and end so many paragraphs with '...and so on.' 

And so on. 'It's all like an ocean!' cried Dostoevski. I say it's all like cellophane."

Sometimes you encounter (surprisingly accurate) chemistry in places you didn't expect.
So it goes.

--
*Bonus: Here's Roald Hoffman interviewing both authors in a 1999 piece for American Scientist magazine

Enthusiasm Goes a Long Way

Earlier today, I watched a scientific speaker drive people out of the seminar room.

Was the person combative? Not at all; a well-respected mid-career chemist at a Top-5 school.
Unprepared? Nope; knew the slides backward and forwards.
Bad material? It was the linchpin talk of the session, so...no.
Perhaps haughty, egotistical, or rude? Still no - a model in professional conduct.

The talk was just, in a word...boring.

Source: Sydney Morning Herald

However exciting the science, you can't capture the audience if the delivery is dull as dishwater. Literally dozens of posts, listicles, humor attempts, even entire blogs (here, here) have been dedicated to the practice of scientific communication. So why don't these suggestions permeate into the wider community? Why do smart people not consider how their message comes across?

I won't go into the particulars of the talk I saw overmuch. Suffice to say that slumped shoulders, wooden expression, monotone delivery, and stiff arms will have your audience reaching for their smartphones in no time. Ditto: wordy slides, insider jargon, and attempts to somehow mash a 50-minute talk into a 30 minute time slot.

One wonders if, after a certain number of conferences, chemists have become inured to terrible talks. Perhaps we should consider installing a "canary" in the lecture hall "coalmine" - a speaking coach or senior faculty member, placed front and center, that can debrief the overall performance after the session, offer pointers, maybe even solicit feedback from the audience.

Optionally, what about Improv? Many fields - business consultants, customer service, construction, education - have benefited from comedy troupes teaching teams to think on their feet. Anyone have something like that occurring at their lab or university?

I'm not arguing that scientific talks be misconstrued as entertainment, yet I feel I could have learned more if I were actively on the edge of my seat, waiting to hear the next assay result or to see the next structure proof.

Anyone else agree?

Synthetic Endgame

Inspired by this paper from Melanie Sanford's rocking organometallic group at Michigan.

--

*Pun contest! I could also have called this post...

Gotta Make 'Em All

Poke-Ball and Stick Models

Chantix Charmander

Putting the Fun in C-H FUNctionalization

'All Thumbs' Synthesis

Friday Fun: Semi-Legal Starting Materials

I ran across this entertaining anecdote today while researching Lord Todd's research into vitamin B1.

From Todd's 1997 obituary in the Independent, written by fellow Nobelist "Kappa" Cornforth:

"[Todd] also worked on cannabis, and in his excellent autobiography A Time to Remember (1983) he tells with relish the story that, having naively imported 6 lb of distilled cannabis resin donated by the Indian police, he had to promise Customs that he would send 25 copies of any ensuing paper to their Bureau of Drugs and Indecent Publications."

Apparently, the "ask forgiveness, not permission" dictum applied in mid-1930s London. It bears reminding that this same choice, made today, would result the appearance of severe gentlemen in dark suits with thick briefcases and Summons in hand at the lab entrance...

Happy Friday,
See Arr Oh

Undergrad Tech: Remember When?

Recently, I sat with a friend sipping coffee, watching passers-by hurriedly moving from one tall building to another. Remarks drifted back towards research - as they're wont to do when chatting with chemists - and she said: "Remember how hard it was just to order things?"

I knew exactly what she meant. Lab tech changes quickly, and you may not even notice until you take a step away from the bench. I'm not part of the generation who spent hours sketching molecules by hand from a rubber template pre-ChemDraw, but nor am I a grad student in the era of tablet computers that can access PDB or Aldrich from a free wireless connection in any lecture hall.

Maybe I'll take a quick stroll down memory lane to see how different things really were when I first started undergraduate research...

Planning: Then, as now, most projects kicked off using pen-and-paper or chalkboard sessions; whiteboards were in about 30% of classrooms and gaining ground, but my first experiences with drawing molecules for my coworkers covered my fingers in tacky powder. I can still smell lab chalk: musty, earthy, sometimes tinged with a faint amine odor if stored too near the reagents cabinet.

Courtesy of Dr. Freddy, at Synthetic Remarks, who seems to recall
chalkboards much more fondly than I.

Once you'd had the discussion, you transcribed it into a lab notebook - usually bound with black vinyl, perhaps featuring brown or maroon faux-leather accents and a bookmark string - and signed the page. Then it was time to dive into the literature. First, you staked out some territory at one of the few hulking beige monitors attached to your shared lab computers. Plan for coffee, since reboots and blue-screen crashes could usually be expected to last 10 minutes, with accompanying Windows jingles or goofy Mac cursor wheels.

(Why were operating systems always a generation behind on shared computers?)

Your 10-minute excuse to go grab a coffee.

Beilstein and SciFinder both offered installed systems with single-user seats. This meant you walked down your lab hallway, shouting "Does anyone need anything on SciFinder?" before logging in. The user interfaces were very Internet 1.0 - muted grey windows, inscrutable black text, fuzzy structures. Mostly, you would up transcribing the reference into your notebook alongside the idea. To get the paper, you usually brought a stack of dimes down to the reference library, and spent the next 20 minutes finding and then copying (don't forget to rotate every other page!) the journal article. The still-warm, toner-scented stapled copies were lugged back to your wooden desk to be pored over until evening. My fingers would often be tinged with more than one color of highlighter or colored pen after a night of intense study.

SciFinder Scholar, 1999. Source: ISTL.org

Synthesis: OK, you know what you want to make, so you need some reagents. Maybe first you glanced through the 2,000-row Excel file your lab has as its de facto "inventory" system. I remember some groups also had a dog-eared, yellowing notebook dangling from a rope of masking tape that listed all the chemicals no one needed any longer - hope you enjoy distillation! Failing these approaches, the trusty catalogs are all lined up against the single lab window, effectively blocking out 20% of the available visual real estate. Names of vendors I remember included Fisher, VWR, Aldrich, Sigma, TCI, and Columbia. Each one had different account reps, pricing, and delivery specs; you'd better believe your boss would ask if you looked up pricey, boutique reagents in more than one source. Someone had the lab job of calling these vendors every few days, providing the lab P.O. number or group credit card, and then taking delivery later that week. Collections of cardboard boxes large and small would be piled near the front door, and every week was Christmas (even if it was just your reagent-grade TEA).

The first and last physical Aldrich catalogs I remember ordering from.
Source: Alfred Bader, Sigma-Aldrich

At some point, you'd have everything needed to run your experiment. Hours passed, TLCs ran, and you scribbled long-hand in that same lined lab notebook. I'm fairly certain I spent thousands of hours hunched over, detailing exactly how the workup went, or scrawling single-line corrections (with initials!) for changes and errors.

Analysis: Instruments fell largely into two camps - things you ran and printed out to later affix into 3-ring binders, or numbers on an LED screen you hastily scribbled onto a Post-it note. UV-Vis and optical rotation fell into this latter camp; I still smile whenever I see a forgotten, tucked-away bookmark reading "+8.75 deg."

I worked in lab right at the death knell of chart-recorders - little red pens in threaded holders that traced a curve based on numeric readouts from an IR or GC. NMR, graciously, always emerged on an ink-jet printer in the corner of a sub-level lab. I was a Bruker shim-jockey for quite a while, bragging that I could shim, acquire, FT, pick, and integrate an 8-scan 1H in under 2 minutes. Of course, many academic labs now have robotic cherry-pickers and automatic data transfer, which must save tons of time (unless you're a biophysicist or monitor kinetics; we might as well chain you to the 600MHz).

Source: Cal State LA / Bruker Instruments

Presentation: My first lab group still owned an overhead transparency viewer, and we were encouraged to print or sketch acetate slides each week for discussion. As these smudged easily when warm or done hastily, there were many grumblings and thrown elbows at the photocopier from fellow labmates on group meeting day. PowerPoint was reserved for "big" talks - oral exams, defense seminars, or preparing a poster for ACS meetings. Once saved and laid out the way you wanted, these were burned onto a CD-R or stored on a 100MB USB flash drive your boss might loan you. The walk to FedEx felt tense, because you didn't want to lose this uncomfortable piece of plastic, which contained the only copy of your slides.

Just don't write on the glass itself, or the PI will get really angry. Trust me.
Source: Amazon

I'm sure that I'm missing more fun events from lab life and technology from the late 20th century. Readers, if you have a special memory from back in the day, please feel free to share it in the comments. I'll update the post if I've missed something vital.

Big Fish, New Ponds?

Have you kept your ear to the ground? Felt something on the breeze? Getting a "gut feeling"?

The most recent edition of Chemistry Bumper Cars - Faculty Moves, for the uninitiated - leans towards bigger deals and dramatic poaches as the Fall term looms over the Summer horizon. Here's the latest I've heard about, with my own opinion about whether the rumor holds water.

Dave MacMillan to leave Princeton, for...?
Odds: Low

I hear what you're saying: MacMillan has already moved twice (Berkeley -> Caltech -> Princeton), and we're talking about a researcher who averages an award every year and a new named professorship every four. However, he's fairly well settled into a tight relationship with Merck, who are local to NJ. He's also helped propel Princeton back up in the rankings over the past decade. I can think of only one university that sounds like any kind of a step up, and they have plenty of organic power at the moment.

Dirk Trauner to NYU
Odds: Medium

Though I've heard this more than once, I'm scratching my head about how it makes sense for Trauner. Part of his motivation in returning to LMU was to continue the Mulzer mystique: the powerhouse European natural products group that makes densely-functionalized products appear as if by magic. Then again, NYU seems to be aggressively searching for a certain kind of chemist; maybe Dirk is slated to be the new Phil Baran of the East Coast?*

Update: As seen in the comments, Dirk himself confirms. My gracious thanks to the Professor.

Tom Rovis to Columbia
Odds: Certain

Signed, sealed, and delivered to Columbia back in the Spring.

Dave Liu to Broad from Harvard
Odds: Low

First he was an undergraduate wunderkind with Corey, now one of the youngest Full Professors and an HHMI scholar, all before age 40. He's already a core faculty member with Broad while managing his Harvard group, and I see no reason for Harvard (or for Liu) to wish to terminate his current position. This may sound like wild speculation or stargazing, but I fully suspect Liu's name goes on a nomination for a Big Prize within ~5 yrs, and I think Harvard would do everything they could to keep him in the fold for that day.

Update: As noted in the comments, does appear Liu will have to be physically present on the Broad's campus.

Karen Goldberg to leave U. Washington
Odds: Low

I very much want to believe, especially since UW lost Jim Mayer a few years back, that they can retain Goldberg, a C-H activation and general OM superstar. She boasts a local Center and a named professorship, as well as a Department with plenty of talented young blood: Boydston, Bush, Cossairt, Fu, Lalic, Schlenker, Theberge, Zalatan, all hired in just the last 6 years, doubtless some drawn there through her influence. I'm sure she'd succeed at a Caltech or an MIT, but I really don't know enough about her motivations to say any more conclusively.

Greg Verdine leaves Harvard to run companies full-time 
Odds: High

It's said you can throw a rock in Cambridge these days and hit a VC. Seeing how much apparent fun and success Verdine has had with his previous ventures into the private sector, I'm betting he continues this line full-time and slowly winds down managing theses and group meetings.

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*Today's ridiculous statistic: In the past 20 years, Baran and Trauner have authored a combined 372 research papers. That's 2-3 entire careers, and these are guys with 20+ years ahead of them. Damn.

Sudden Tamiflu

Hey there, JLC fans! Long time, no post.

Today's inspiration comes from a molecule I've enjoyed watching the synthetic, process, and educational chemistry communities go to town on for the past 18 years: (-)-oseltamivir, also known by the trade name Tamiflu. See that cyclohexene in the middle? This molecule mimics the transition state of a mostly-flat oxonium cation derived from sialic acid, so well that it interrupts the flu virus's ability to release further infectious particles, allowing the body to "catch up" and reduce overall time spent hovered over a steaming bowl of chicken noodle soup.

But enough about the Why, let's get to the How; as the authors of this paper pitch in their opening line: Time is Money!

Hayashi and Ogasawara, no strangers to Tamiflu themselves (syntheses in 2009, 2010, and 2013), report in Org. Lett. ASAP a synthetic economy we don't always consider: time. They claim a one-pot Tamiflu synthesis, five steps, average step yield around 70%...finished in just 1 hour.*

Compare that against the benchmark of the previous 1-pot reaction - 57 hours. Wow!

Several interesting modifications to their previous syntheses have enabled this savings. First, addition of a hydrogen-bond donor catalyst to a nitro-Michael addition, which accelerates the reaction 3x. Second, swap of a base in an HWE reaction: 3.5 hours in cesium carbonate becomes 20 mins in tBuOK. Finally, a sacrificial move - rapid epimerization of the penultimate nitrohexene, knowing that only 50% of the product will successfully reduce to the desired diastereomer.** A short silica column completes the rapid realization of this antiviral drug.

Lest you believe that I'm hornswoggled by a synthetic sprint, a quick glance at the Supporting Info*** provides a cold shower. There's some lingering impurities in those 1H NMRs, enough to make me believe that the yield, even at gram-scale, isn't really 16%. And the reagent equivalencies used to drive these nitro-boosters aren't pretty: 30 parts Zn, 3 parts phosphonate, 15 aliquots of TMSCl. To touch upon an allusion the authors themselves make - perhaps a Jamison-style flow reactor is the next logical step for this speed-demon of a route.

--
*As I wrote this line, I couldn't stop comparing this to other "just 1 hour!" claims from consumer products: teeth whitening, photo development, tax preparation, LensCrafters, oil changes, and pizza delivery can all refer to the 2016 Hayashi Tamiflu synthesis as a spiritual brother of sorts.

**I don't believe that there's a spontaneous kinetic resolution here, but if any sharp-eyed reader can prove differently, I'm all ears.

***Counter-counterpoint: The one-pot is so streamlined that it now takes only 281 words to synthesize Tamiflu. 
Damn.

Postdoc Required? Check the Job Ads!

Both the New York Times and C&EN have written pithy pieces today referencing the recent Science survey about factors influencing postdoctoral study. 

The tone of all three comes across as confused, painting Ph.D. students as ill-informed, directionless lambs who take on postdoctoral appointments as, in the words of the Science authors, "default...holding patterns" because they "...don't know what they want to do with their lives." (NYT).

Well, for those of us, like me, who postdoc'd with the intention of going into industry, why did I "waste my time in a post-doc" (Science) for seemingly no reason? Here's some telling quotes, highlighting from me:

From Science: "...career goals are quite diverse even among these postdoc-planning students...[t]his may be surprising, given that the postdoc is not typically considered a stepping-stone toward nonacademic careers"

From C&EN: "Many students don’t have a sense of how many jobs are available or what background they require, Doyle says. Chemistry students think they need a postdoc for some high-level industry jobs in the pharmaceutical industry, for example."

From NYT: "[in 2013]...the most common reason students gave for doing a postdoc was that they thought it would increase the chances of getting the job they wanted."

These sound bites sound aloof at best, slightly pandering at worst. Here's my question: Did anyone quoted for this story, or the authors of the Science study themselves, actually read the job ads for the industrial positions in question? Maybe students' fears are well-justified, because the ads I'm seeing from multiple companies read like this:

GSK, API Chemistry Automation Team Member

Pfizer, Sr. Scientist - Obesity + Eating Disorders

Amgen, Scientist, Immuno-Oncology

Genentech, Sr Scientific Researcher, Discovery Ophthamology

In case you missed it, all recommend postdoctoral research. I didn't have to go digging for these, either - simply typing "chemistry" along with "postdoctoral" or "post-doc" into the Career search engine on any corporate site will reveal roles like these. I find it rather ironic that the last quote from the Science lead author reads: "We don’t know enough about the industry labor market” (C&EN write-up). That seems to be the only part of this whole situation I completely agree with. 

OK, grumpiness aside, how can this situation be fixed? I actually appreciate the incentive strategy advanced in the paper, which neither news outlet captured well. Here's most of the penultimate paragraph from Science, highlighting again mine:

"Whereas the recent National Academies report recommends that students make career plans early in the Ph.D. program, we argue that they should consider labor market conditions and career options before starting a Ph.D. program. Doing so may avoid escalating commitment to a research career and may prevent individuals from entering a postdoc holding pattern. Graduate schools could encourage career planning by requiring that applicants analyze different career options and justify why a Ph.D. is the most promising path forward. Funding agencies could implement similar requirements, especially in conjunction with moving a larger share of funding from research grants to training grants and individual fellowships."

Amen. One thing I believe saved me from five years of postdoc purgatory was walking in "eyes open," understanding exactly what jobs I'd qualify for and where I needed to end up to pay back all my student loans. I also realized it would be no cakewalk: I began applying for jobs in my second year of study, and never looked back. 

Grad students: If you're confused about your options, feel free to drop me an email at seearroh_AT_gmail. Confidentiality guaranteed.