Who the R.F. Heck is: Henry Eyring

The subject of the advanced organics class this week is rate laws and transition states. With that, there have been many different names thrown around, Hammond, Morse, and the like. But none have been more prominent than Henry Eyring.

Eyring was born in a Latter-day Saint (Mormon) colony in Mexico in 1901. When he was about 11 years old, the family moved to Pima, Arizona by way of El Paso, Texas. He showed apititude for science and math, and after studying mining engineering, metallurgy, and chemistry, he pursued his graduate studies at UC Berkeley. He was recruited to Princeton where he taught for 15 years until he was offered a position at the University of Utah. He was elected president of the ACS in 1963 and the president of the Association for the advancement of science in 1965.

His religion was very important to him. He was a devout Mormon and wrote many books and papers on the subject of Science and Religion. Of his three sons, two went into science and education, while a third, Henry B. Eyring, is a prominent leader in the Latter-day Saint church.

It is arguably this reason that Eyring never received the Nobel Prize for his work. He developed Transition State Theory, one of the most important developments in chemistry ever, and some received Nobel Prizes based on his work. The Royal Swedish Academy of sciences apparently did not understand his contributions until after his death in 1981, however some argue that there was prejudice against him for his quirky personality and his religious beliefs. He eventually received the less prestigious Berzelius Medal in 1977.

What this means to you, the undergrad: Do science for the love of science. Make breakthroughs for the sake of advancing human understanding; any prizes are merely nice afterthoughts.

-Woodward

Nobel Prize in Chemistry

Early this morning the Nobel Prize in Chemistry was announced. Three scientists -Martin Karplus of the University of Strasbourg and Harvard University, Michael Levitt of Stanford University, and Arieh Warshel of the University of Southern California - will share the prize this year for their work in developing computational chemistry. Together, the three of them developed the tools necessary for modeling reactions that take place on a atomic level using computers back in the 70's. You can read the NPR summary here.

Some argue that the choices for this selection were not spot on 100%. Many agree that Karplus is deserving of the award, but the others are debatable. What should be clear is that this award is really going to the field of computational chemistry, but the committee needed some faces to go along with it.

So what should this mean for you, the handful of undergrads that read this blog and therefore the intended audience? It means that we should honor those who went before. It means that every time you read about some basic and not-so-basic reaction in a textbook, someone has probably used a computer to simulate that reaction. It means that in our very near future in industry, we will be using these advancements to design drugs and materials before getting to the lab. It means that this field is so important today, that the committee decided to honor it forty years after the fact. And it means that you are not likely to get out of college without knowing something about it.

Link to the official announcement

What do you think? Was this the right call? Are the three scientist deserving of the prize? Who else would you include? Leave a comment below.

Notes from Group Meeting 3 - Leaving Group Violations

Sorry for the delay, recently upgraded the computer and didn't have access to the wonderful world of ChemDraw. This post will be about the first meeting, and a second will come later this week on last weeks meeting.

This past Thursday fulfilled its promise of group problems. The majority of them, however, were something you would see in Sophomore Organic Chemistry. Sure, they were some upper end stuff, but Sophomoric none-the-less.  It did provide an opportunity to council younger students on the dangers of saying "never".

The two problems shown here each have an abnormal leaving group. The first scheme can be written a number of different ways, but it is generally agreed that the final step is the displacement of a hydroxide group. Normally, you would never see it, but in basic enough conditions you can work some magic.

The second reaction (presented here to work out on your own) shows a methyl as the leaving group, again, a big no-no. Yet, through the magic of Iodoform (hint-hint) reactions, it can pop right off.  Have fun!

-Woodward

Class Notes 2 - Heitler-London Theory

It's been a while, what with school getting under way. But I have a minute for a quick post, so I'll take it.

In Advanced Organic Chemistry the other day, we briefly talked on the Heitler-London theory. We were really getting into Valence Bonding theory, and the professor mentioned the theory in passing before moving on. So of course I had to look it up.

Walter Heitler was a German chemist who, among other things, advanced Valence Bond theory to a higher level of understanding. He applied Schrödinger's wave equation, recently published the year before, to the wave-functions of a hydrogen-hydrogen covalent bond.  He then called up a young Fritz London, and together they worked out the details of the theory that night. This theory really marks the beginning of "modern valence bond theory", and is still useful today. (Although, as I understand it, MO theory is used for most calculations.)

I'll talk more on London another time, since he has such a  remarkable career.  However, let me comment on the life of Heitler. He made significant contributions to chemistry during his time, was on the board or was the head of a number of universities, and faced a not insignificant amount of persecution. He was Jewish at the time Hitler came to power in Germany. Thankfully, Max Born was able to secure him a position out of country in Bristol, and was spared for the most part from the dealings of WWII. In his later life, he wrote a number of books on the philosophical reasoning of science and religion, which is not something we talk much about these days. (Perhaps another blog post on this front?)

Bottom line, let us honor our scientific ancestors and respect the work they've done. Standing on the shoulders of giants and all that.

Notes from Group Meeting - 2

School year officially started this week, meaning we finally have group meetings again. A couple of people were mentioned jokingly between professors that I had to look up, cause I sure don't want to be left out of the loop.

The first person was Phil Baran. We were discussing a synthesis, and the presenter showed how a group achieved their goal by performing six steps to protect, oxidize, deprotect, an so on. Professor B said to Professor A (paraphrase), "With that many steps just for protection, Phil Baran must be in pain!"

Google tells me Phil S. Baran is a professor at Scripps, and his focus is on "Aiming for the Ideal Synthesis". His mantra: "Total synthesis in this century must therefore be keenly aware of this ultimate challenge – to be able to provide large quantities of complex natural products with a minimum amount of labor and material expenses." He follows JB Hendrickson's dictum, …creates a complex molecule… in a sequence of only construction reactions involving no intermediary refunctionalizations, and leading directly to the target, not only its skeleton but also its correctly placed functionality." He recently published in Science about a 14 step efficient synthesis that his group performed. He is well respected in his field. Many of his papers are protecting group free, and would be considered 'elegant'. Hence, the joke from Prof B to A.

The second person, I didn't actually get his name down, or exactly what happened. We were taking about ethics with all of the apparent fraud going on, and Prof A mentions Jim/John/Joe McNair/McClair/McBear and how he faked his NMR spectra for cylcohexanol (?). This was the big deal in the 90's, or so I'm told, long before I was ever in the industry. I wish I could find more on him, but the internet gods are not with me today. If you know more or can find something interesting about this, contact me and I will put more about him in. Anyway, that's all from group meeting this week. Next week there are practice problems, so I'll see if I can dig up anything fun/interesting/juicy about them.

-Woodward

Edit - Chris Vonnegut and Joshua Sacher (@ArgyleAardvark) have found who I was talking about. James LaClair was the man who published a synthesis of Hexacylcinol, in 2006.  Check out the blurb on Wikipedia.

What the R.F. Heck is: a Lignan?

(See what I did there? That's clever and you know it, even if it is overused)

Getting back to the roots of this blog, it's time I talk about something that made me look it up. The current synthesis our group is working on, a molecule with no name yet, is described as a "Lignan".  It is also described as a number of other things as well, but that's going to require more space than I have to cover it all. But, in an effort to understand more about this molecule, I did have to look up "lignans", and since that's the case, I have to blog about it as well.

Lignans are a group of chemical compounds that are mostly found in plants. They generally take the form of two aromatic ring, usually phenolic, connected by a chain that, on some level, can be considered symmetric. An example of a lignan is Enterodiol.

They are a major subgroup of the estrogen-like phytoestrogens and can act as an anti-oxidant, making them pharmacologically interesting.

What you don't want to do is get these confused with lignins, which are much larger compounds commonly found in wood. (As a side note, most of the artificial vanilla made today comes from lignins as a by-product of the wood-pulping industry.)

However, both lignans and lignins can be formed by a precusor called a monolignol. These most commonly take the form of substituted cinnamyl alcohols.  In fact, the first step of our groups synthesis is forming a substituted cinnamyl alcohol.

If you wanted to go hunting for lignans, you'll most likely find them in sesame seeds and flaxseeds. Mammals can modify some lignans ingested and create their own too. New lignans are being discovered regularly, too. Li, Zhenxing et al. published a paper in Chemistry of Natural compounds describing two lignans found in the roots of the Chinese Fir back in May of this year.

Sorry this post is not as interesting, but its a great way to keep learning and be able to better converse with your peers.

-Woodward

Chemophobia - and How to Deal With It

In the post Keeping up with the Jonses I talked about trends in Organic Chemistry, discussing things like 'green chemistry' and calcium catalysts.  On a more meta level, there are trends about the discussion of chemistry, on blogs, podcasts, etc. In case you haven't been keeping up-to-date, Chemophobia (if your Latin's a bit rusty, "the fear of chemicals") is the go to topic ('fraud' also happens to be kind of big too). I figure I should throw in my two cents (0.0128 pounds sterling at current exchange rates).

In popular culture, it is fashionable to be afraid of chemicals. I'm not saying that people are running in fear, just that they tend to avoid it when possible. Natural diets, home cures, organic foods, and the like are all the rage and promoted by high profile individuals. There's nothing wrong with a person's right to choose how they live their lives, but it brings about a fear of anything that can be labeled "unnatural".  And as much as we despise it, the word "chemical" has been branded "unnatural".

Can't really blame the people, there have been some unfortunate run-ins with "chemicals" in the past; DDT and Agent Orange come to mind. It is unfortunate the bad consequences of these chemicals have been placed on good chemicals as well.  Pesticides and prescription drugs all get a bad wrap. Public reaction, however, has become over-reactionary. Walk into a your local big box store and you invariably find soap, cleaners, and the like labelled as "chemical-free".  Never mind that it still has chemicals like water in it.  Never mind that the formula hasn't changed in 50 years. People will appreciate and gravitate towards these products because of the pejorative use of the word chemical. And this sort of use of the word 'chemical' will continue until chemophobia starts being less prevalent. And how do we that?

By making Chemistry more accessible. The argument has been made that Chemistry is the least accessible science. Astronomy has lots to look at, physics makes roller coasters go, biology is squishy but still understandable. Chemistry doesn't have any sort of equivalent. It is inaccessible to the Average Joe.  One of the reasons I started this blog is because I felt much of the chemistry going on today was inaccessible to an undergrad as well. We need to find ways in which chemistry can be more easily understood by the population in general, not just by professors and post-docs. This will be an uphill battle, and there is no easy solution, but if we start now, by blogging, talking with friends, using social media, and the sort, perhaps we can make chemistry a more friendly field for the next generation of scientists.

-Woodward

A great article at The Collapsed Wavefunction talks about not "punching down" chemophobia.
See Arr Oh wrote a great article highlighting the pervasiveness of chemophobia at Just Like Cooking.
Here's a graphic that shows how everyday chemicals can have scary sounding names.
Edit - Perhaps xkcd has the best way to deal with chemophobics