Tuesday, October 23, 2012

Personal Log, Stardate: Mole Day

Well, I certainly 'fished my wish' for this carnival! Only two days in, and I've already compiled the requisite 10 entries for my own post. So, here goes...

Your current job: I'm a medicinal chemist at a (very) small startup company. How small? Let's just say that everyone at the company still fits around one table for lunch.

What you do in a standard work day: Like many folks at small companies, there's hardly a 'standard' day; I rapidly shift between lab and non-lab responsibilities. For instance, in the past month, I've written grants, met with vendors, fixed small equipment, scaled-up our final product, drafted provisional patents, tested new routes, and (nearly) finished our safety handbook. 

Never relaxing, but never boring.

What kind of schooling / training / experience helped you get there? Since I use the #phdlife hashtag from time-to-time, it shouldn't surprise you that I have my doctorate. But let me tell you why I went back to school. I had been working as an RA at a medium-sized biotech back in the "boom years." Every Friday, the Ph.D. chemists would meet in a conference room, and emerge with fresh data and synthetic ideas. 
Patriots coach Bill Belichick
attended Wesleyan around the time
Max Tishler became a chem professor

I wanted to be like them. 

[Soapbox Moment] - I can't recommend enough actual lab work as an intern or undergraduate assistant. Without that experience, I'd never have become a chemist.

How does chemistry inform your work? My nose often points into the pages of Aldrich, Alfa, Fisher, Green & Wuts, and Silverstein & Webster. Reaxys and the primary literature feel like best friends. Thick binders of NMR and HPLC data festoon my top shelves. I'm known to doodle structures on nearby scrap paper, so don't throw away anything on my desk, please!

Finally, a unique, interesting, or funny anecdote about your career: Gosh, lots of 'em. Moving shaky mercury-filled Schlenk lines on rusty old elevators (not recommended). Nearly catching myself and a balance on fire during my first week as an intern. Grading huge stacks of tests while blaring terrible pop music and noshing on pizza.

Here's one I suppose informed the theme of this carnival: my High School chem teacher was also one of our football coaches! So, periodic trends in class, linebacker drills on the field.

One more - Didja see the post title? I still recall one of my early "Aha!" moments as the ST:TNG episode "Night Terrors," where the alien race describes hydrogen as "eyes in the dark, one moon circles" (one proton and one electron). Must have really stuck with me!

Monday, October 22, 2012

Chem Coach Carnival, Day One

It's a gorgeous Fall day outside, a perfect way to kick off National Chemistry Week 2012. We've had a few bites on the #ChemCoach carnival already, so let's cut to the chase.

1. Julie, Associate Faculty. Julie blogs at The Stoichiometric Equivalent. She's a new mom, currently teaching one class. Julie teaches labs, lectures, grads, and maintains Blackboard for her class. She was hired in a most unusual way (as chemistry profs go) - by playing a flute concert. Way to be first, Julie!

2. Azmanam, O-Chem Lecturer. Adam blogs at Chemistry Blog. He's psyched to be doing exactly what he always wanted to do - teach chemistry - and has a bunch of really fun stories about on-the-fly analogies, 'suctration,' and Peyton Manning.

3. Laura, President and COO, Quintessence Bioscience. Laura blogs at The Next Element. She wears a lot of hats. She was Employee #1 at a small start-up biotech, and has optimistically slogged through 22 Wisconsin winters.

4. Stephen, Assoc. Prof. and Department Chair. Stephen blogs at The Simple Candle. Instead of a traditional postdoc, Stephen returned home to Oklahoma City to found a new charter high school. He knows a hydrogen bond when he sees one, and students have called him "1% man, 99% science!"

5. David, UK Undergraduate. David blogs at Chemically Active. He has a bunch of great advice for UK-based students seeking chemistry careers. Once, during an interview, he blurted out something that was "part truth, part guess, and part utter tosh." (We've all been there)

6. Stuart, Chief Editor, Nature Chemistry. Stu dabbles in writing, mostly at The Sceptical Chymist and Chemical Connections. He serves as a bridge between referees, authors, Editors, and the public, while also taking a long view towards future development of the journal. He (correctly) opines that "sometimes the subtleties of chemistry are lost on non-chemists."

7. Dawn, Sustainable Technologies Assoc. Director, Dow. Dawn sent me her entry by email, so I'll post it here, as promised:


"I work for Dow Chemical in the department of Sustainable Technology.  Our goal is to help our scientists, developers and marketing community imbed sustainable chemistry and engineering at the earliest stage of technology development – a “get it best early on” mentality.  This is accomplished through meeting the needs of People (technology has to function well, meeting a consumer need), Profit (if it isn’t profitable, we won’t be in business for long), and Planet (minimizing the impacts).  Specifically we aim to

-          reduce hazard (product, process, use of our products),
-          improve energy footprint (energy efficiency in our plants; energy efficiency for our customers through the use of our products; diversified feedstocks; technology for renewable energy),
-          maximize atom economy through optimal yield, lowest auxiliary use (solvents, protecting groups, etc.), minimal waste, and even concepts like optimal functional unit efficiency (e.g., meets the performance need but maybe with double the lifetime, thereby maximizing every use of those atoms as compared to an incumbent technology),  
-          and holistic design – considering “cradle to cradle” concepts that explore the use of renewable and recycled raw materials, a sustainable supply chain, through customer use phase, and end-of-life scenarios.

My typical day involves elements of training, project consulting, reporting on sustainability metrics, tool development (like sustainability assessment tools for early-stage projects), and university sustainability workshops (we’d like everyone to learn these principles early in their undergraduate and graduate education!).

I have a Ph. D. in Organic Chemistry and was a post-doctoral fellow in Bio-organic Chemistry.  I have 22 years of industrial experience in a variety of leadership roles across many of Dow’s business and corporate research teams, as well as diverse geographical experience with global responsibilities, including assignments in Europe and Asia.  My experience includes businesses and technologies such as Dow AgroSciences, Corporate Research - New Products & Math Modeling, Dow Building Solutions, Specialty Films, Plastics, Asia-Pacific Corporate Research, Asia-Pacific Epoxy and Specialty Chemicals, and now Sustainable Technology. 

My most unique experience was being on assignment in Switzerland (the richest country in the world) and then to Shanghai, in a developing economy.  Quite a juxtaposition of experience!  In Shanghai I was part of the leadership team that established a world-class research capability.  Key contributions during this last assignment included business research responsibilities as well as establishing a solid foundation in Dow’s Environmental, Health & Safety culture and practices across our new research organization.  It was the most rewarding experience of my career.

I have a personal passion for sustainability and achieving scientific innovations that have a positive impact on the world – a passion that became a catalyst for change in several of the Dow businesses I’ve served."


SAO here again: Wow, guys! I can't believe I've just received seven entries on the first day! Keep 'em coming, and don't forget to use the hashtag #ChemCoach on Twitter.

Sunday, October 21, 2012

Announcing: The Chem Coach Carnival

Do you work in chemistry?

Want to help folks interested in chemistry do what you do?

I like to think about chemistry
during timeouts.
In celebration of the 25th National Chemistry Week (Oct 21-27, 2012), I've decided to host a blog carnival called the Chem Coach Carnival. (Unfamiliar with the carnival format? Check out the "Favorite Reactions," "Toxic," and "Science Writer" carnivals)

Why the theme? After writing a tongue-in-cheek post last week, I received several comments through email, Twitter, and on the blog about an actual online repository of chemistry job success stories. Wouldn't it be nice to ask professionals questions like these?

What do you do all day? What chemistry skills do you use in your line of work? How do you move up the ladder in chemistry? What do I need to do to be in your shoes?

Here's the specifics: To keep the carnival timely - and since I didn't give a lot of advance notice (sorry!) - we'll keep posts short, about 300-500 words. If you'd like to toss in a (small) picture that helps the reader, go ahead. The general structure will be:

Your current job.

What you do in a standard "work day."

What kind of schooling / training / experience helped you get there?

How does chemistry inform your work?

Finally, a unique, interesting, or funny anecdote about your career*

The most important question to ask yourself - If I were just coming into the field, would I learn something useful from your story?

Whaddaya mean these mechanisms
aren't right?
I also want to stress that you don't have to be a blogger or writer to participate. I'd love to hear from every kind of chemist: professors, bench chemists, formulators, artists, Wall Street advisors, authors, Editors, engineers, grad students, historians, Olympiad participants, forensic scientists, safety officers, advertisers, biochemists, Nobel laureates, you name it.

Everyone is welcome.

As far as posting, you can either post on your blog and I'll link to it (preferred), or I can take your entry by email (seearroh_AT_gmail_DOT_com) and post them on Just Like Cooking. If you've posted something, send me a line at @seearroh or use the hashtag #ChemCoach.

I look forward to celebrating National Chemistry Week by reading about all your employment adventures. Thanks in advance!

*Bonus motivator - I'll be writing a post, too, but I'll only post mine after I receive at least ten entries from around the campfire. Happy writing!

Saturday, October 20, 2012

Picture Book: Fall

Thus ends the first week where, Chemjobber-style, I tried to write at least one post per day. Thought I might reward myself with a pictorial post. I'm not the world's premier photographer, so bear with me...

Hard to tell from the photo, but this is about 6" tall!
Familiar to anyone?
Train station: a "grey-dient" runs L to R. 
Triple helix banister
Dichloromethane: slow evaporation, humid room
Huzzah! I've solved the liquid helium shortage.
Every food should appeal to consumers this way.

Goodness Gracious, Great Balls of...Sunscreen?

Actual AP headline yesterday: "Banana Boat recalls sunscreen due to fire risk." CNN, ever one for a scare, upped the ante with their headline: "Sunscreen could burst into flames on skin." (emphasis mine). Did I miss the part when sunscreen formulators started including white phosphorus in the mix?!?

Kidding aside, I'm not talking about "toxic chemicals" here; sunscreen already occupies a special place at Just Like Cooking due to the clouds of chemophobia swirling around it. The fire risk appears to involve two factors: engineering and consumer usage. An Energizer Holdings* corporate spokesman said the canister spray valve applies too much product, which leads to longer-than-average drying times. The exacerbating factor? Customers suffering burns engaged in barbecuing and welding immediately after application.

Well, what is so flammable about spray-on sunscreen, anyway? The ingredients list shows all the usual suspects: UV blockers, vitamins, surfactants, and polymers - none of which are particularly flammable. Two components catch my eye, though: isobutane and SD Alcohol 40. One commonly finds isobutane, the simplest branched hydrocarbon, in refrigeration coils and aerosol products. It could certainly ignite, but high volatility means that most of it flies away mere seconds after you spray it on. SD Alcohol 40**, however, is almost straight ethanol, and makes up a large portion of the overall spray. It would also fit the bill for physical properties: boils at 173 deg F, vapor pressure 40x lower than isobutane. A fog of ethanol slowly evaporating from your arms certainly invites ignition.

*Fast fact: Did you know Energizer Holdings owned Banana Boat? I didn't. They also apparently make shaving creams and tampons. Huh.

**The Code of Federal Regulations (CFR) actually tightly regulates specially denatured (SD) alcohols for use in lotions, oils, creams, and sprays. Here's the page for blend "40." I was rather surprised to find out that sunscreen actually contains trace amounts of complex alkaloids: quassin, brucine. The bitter taste and side effects discourage drinking SD-40 for recreation.

Friday, October 19, 2012

Friday Fun - Up, Up, Up The Mountain Ahead

Dream big, kids.
When you join a new company, you instinctively adapt to the work pace, flow, and org chart. Some changes take longer than others, and I believe, like Yogi, that "90% of the game is half mental." It takes time to wrap your brain around unfamiliar information, and job titles are part of that adjustment.

What do I mean? Work in science awhile, and you'll collect proper nouns like Halloween candy. Chair of some committee, Head of a department, Scientist 1,2,3,4...infinity. Manager, Director, Prez, Chairman, and of course "Senior" or "Emeritus" appended to every title later in life.

Germane to our earlier discussion about chemistry "life coaches," I feel the community needs a list of all the different things you can do in chemistry, parsed artificially by job description. Here goes, from bottom to top, best I can muster (suggestions welcome!):

That Kid who likes Science
Student
Test Tube Washer
Intern
Science Fair Winner
Chemistry Major
Teaching Assistant
Science Fair Judge
Tutor
Technician
Research Assistant
Grad Student
Research Associate
Lab Manager
Scientist
Postdoc
Habilitant
Assistant Professor
Adjunct Professor
Research Chemist
Associate Faculty
Visiting Professor
Manager
Grantee
Hey, look, a hyper-literal metaphor!
Scientist II
Principal Scientist
Senior Scientist
Specialist
Associate Professor
Senior Chemist
Project Head
Special Advisor
Senior Manager
Chief Scientist
Assistant Director
Full Professor
Associate Director
Dept. Head
Director
Chaired Professor
Vice President
Assistant Dean
Chief Scientific Officer
Research Fellow
Advisor
Dean
Vice-Chancellor
President
Vice-Chairman
Chairman
Ribbon-Cutter
Laureate
Chancellor
Board Member
Knight / Dame
(see post title)
CEO
Founder

...and, of course: "Emeritus" (everything above).

Readers, what did I miss on this life expedition? Suggest 'em in the comments, and I'll toss suggested titles in where I think they fit best. 
Happy Friday!

The [3,9] - Reach Exceeds Grasp

Fight in the organic octagon long enough, and you're certain to come across boatloads of sigmatropic rearrangements. There's your classic [3,3] - Cope, Claisen, etc - the [2,3] Wittig, and [1,3] hydride shifts. Sometimes, interlopers crop up, like [4,4] and [5,5] shifts. Molecular modeling even lends support for a [7,7]!

But have you ever seen a [3,9]? Can you picture what such a system might look like? Well, Wegner, Kessler, and Neuburger (Basel) would like you to try. As they report in their latest JACS ASAP, they've posited a rather cool [3,9] to explain the products of a tandem IEDDA (inverse-electron-demand Diels-Alder) followed by a cyclopropanation:

Wegner et. al., JACS 2012
Toss out everything you learned in second-semester organic. The authors describe an "...'allowed' supra-antarafacial [3,9]." This means that the oxygen atom of the putative dihydrofuran lets go from the "top" face, while at the same time the cyclopropane forms on the bottom. They've run calculations on the system, and metal-stabilized versions have been shown to react in similar ways. Heady stuff.

Even more interesting? The catalyst is a bidentate diboron Lewis acid. That's right: each boron atom grabs hold of a single nitrogen atom in the diazine to promote the D-A (You don't see that every day!) The authors make a tiny squeak at the end of their paper regarding possible future synthesis of 'unsymmetrical' versions of their catalyst. I bet that that'll be tough, given the proposed transition-state binding model - one ring flat, one sticking straight up at the incoming dienophile.

My guess? They'll likely try to hang a helically-chiral group on one side, or else staple a PHOX or Evans auxiliary on. 

Time will tell.