chemistry in the briny deep ... sort of

When I was a graduate student I simplified a synthetic route and foolishly included an interesting conjugate addition of a cuprate. Eventually I got the details worked out, but spent quite a bit of time learning the intricacies of the voodoo that is copper chemistry. Ever since then I've read Bruce Lipshutz papers when they pop up. He has always seemed to do interesting chemistry, whether mundane or exotic, and does a halfway decent job of explaining the practical aspects of the methods.

Nothing pisses me off like some fucker publishing an incredibly skewed "new" method, that is just a rehash of someone else's work, and a quick perusal shows it is just a series of incredibly loaded substrates with no real utility.

So today I was in the midst of catching up on my reading that has piled up over the last few days, and there is a Lipshutz paper in the Org Let ASAPs for 12-23-08. It's basically about a surfactant type ligand for RCM catalysts, something I would have normally blown right by, but since it's Bruce I figured I would check it out. Nothing really struck me until I got to this:

Seawater? Hells yeah!

This has to be the stupidest/most awesome thing I've seen in a paper in a while. I can only imagine what the discussions leading up to that reaction involved.

This reaction works so well that I don't even need HPLC water, tap water works!
Screw tap water, try it in that dirty muck-filled bowl you jokingly refer to as a coffee cup.
Better yet how about in a can of Coke or a beer?

Eventually settling on something that is only just outside the line of reason.

It reminded me of a joke a long time ago between me and some post docs in the group about quenching reactions with pee. If you actually did it, how would you write it up properly? What sort of comments would acccompany the standard notebook boilerplate? "Next time clamp chair" or perhaps "I can't quench it when you're watching"?

Texas is big, real big

I just found out that there is a Texas A & M in Doha, Qatar. I suppose it makes sense that strong american programs want to expand to magnet areas like Education City, but it just seems odd to me that a state school, with its parent state as part of it's name no less, is in another country.

the Palin goodness just won't stop

The GOP should just come right out and sell her as both hotter and less evil than Cheney, and stop trying to actually make her seem like a good candidate on her own talents.

Package Of Bacon Forces Evacuation

Could anything possibly be as bad ass as this headline? I think not.

Oddly enough this pork related attack had nothing directly to do with vegans, Jewish people, Muslims, or any other swinophobes.

the delicious offender being removed by a properly trained professional

Apparently the representative who's office was attacked with nitrated goodness, has some constituents who feel signing the $700 billion bailout is pork barrel spending. Interesting because a spokeswoman said "... he (Boehner) has spent his career fighting pork barrel spending.".

And the best part: no injuries were reported.

politics 3: Sarah Palin with a vengeance

Apparently Governor Palin has some fans and enemies out there. Who knew?

Here is a lovingly crafted depiction of her devotion to our great country and its freedoms:

all she needs is a can of light beer to complete her ensemble

And here are some fun factoids from Rolling Stone magazine.

I have no idea of the veracity of the claims, but I love the fact that they have political commentary at all. Sort of like looking for the hottest new jams in the Wall Street Journal. I suppose it should be "teh hawtest nu jamz", or some such thing, actually.

miracles of modern science

I just read an article that came out in nature a few months back, that is so intriguing I had to share. I unceremoniously ripped it off and have it here for your viewing pleasure.

Nature, 2008, 453, 267

There are so many wonderful things in this teeny article it's hard to know where to start! In ongoing research to reduce the failure rate of condoms, which seems hover at the 1% mark, a team developed a testing device to more closely mimic real world conditions. The novel machination's aptly named 'thrust-hole' is adjustable to, presumably, mimic the differential in opening aperture one might encounter with differing partners and/or orifices.

To determine the type of failure that was in need of alleviation 972 condoms with breaks that had been returned to the company were examined. What a fun job, isn't science neat?

Politics - Part 2

This is the funniest thing I have seen in quite a while.

lab safety

Right now we're in an interim space while our new lab is being located, designed, and built. This particular space is devoid of synthetic chemists save us, and so hoods were not an important part of the original design and there are too few of them. We have approximately two people working in each hood, depending on how you look at it.

Last week my hood mate, who is a decent researcher, made a simple mistake that ended up with a face full of butyllithium.

I wasn't there when she had her accident, but what I was told transpired was: she transferred a large disposable syringe full of BuLi to a reaction, tried to refill the syringe from the BuLi bottle, it got stuck, she wailed on it, it came apart, BuLi everywhere.

Most of the BuLi didn't make it out of the hood, the stuff that did landed predominantly on her gloves, coat, and safety glasses, but some hit her cheek and lip. Both got burned and today she is missing a small patch of skin on her cheek.

Hooray for safety equipment!

She did almost everything correctly, and the thing she did incorrectly is a thing I feel a lot of people would similarly do incorrectly. I think that most people's reaction to something they want to move which resists is to try to move it with more force. It's always a good idea to think before you go back and wail on it, even if the appropriate solution is, in fact, to wail on it.

By the way, she's ok. She got a burn on her cheek where it took off some skin, and got some on her lower lip, which swelled nicely. My feeling is that most of the swelling came from worrying at it, but I don't doubt that it felt none too pleasant.

lovely, lovely computers

I was riding my motorcycle in to work today and I saw one of these for the first time:

ooooo, pretty

I was too far to be able to read it, but I could easily make out the puzzle pieces. The first thing that popped into my mind was "Why would anyone want to protect the plug-ins?".

Firfox + add-ons = sweetness
Safari is for losers

I need to get out more. Or at least spend more time at my bench instead of my desk.

politics

We have a guy working in our lab, who is a retired volunteer researcher. He's in his 80s and spent the bulk of his career working in one area as a PI, and moved to chemistry, I believe, after he retired. He likes coming in and working at the bench, and talking with the other researchers. In general he's a really nice guy, an exceedingly hard worker, and very thankful for assistance he gets, when he needs it. He even asked me to learn about reading proton NMR recently (he had a lab tech do it for him before), and was really into the undergrad NMR training web pages I found for him.

As is not uncommon for someone of his general background he's extremely conservative, politically. He's good natured about it, and likes to make jokes with the more politically liberal lab members, which is a bit unusual, but very welcome.

Yesterday we were talking about politics in a general sort of way, and the coming elections' main players. He mentioned he's a registered Democrat, which I thought was a joke, but he claimed to be true. He said that while the GOP was his party, the primaries were very boring. That and he likes to go to the competing party's primaries and vote in such a fashion as to fuck things up just a little bit.

While my political leanings are pretty opposed to his, I think he may be my new hero. Long ago I had thought that would be an interesting and nefarious way to massage the system, but hadn't the motivation to do it. Talk about balls, damn.

"so I was doin' this chick in the pooper, right?"

Why don't more conversations I'm involved in start this way? That conversation is going to be nothing but gold, whether it's heard from a guy or a girl. Of course girl would be way more interesting.

I mean there is really no downside. If it is an awesome story of sex and debauchery, of course I want to hear it. If it is an awesome story of sex and debauchery with some sort of odd twist (interruption, mistaken identity, loss of consciousness), also wanted to be heard. If it is a story purporting to be awesome and of the sex and debauchery variety, but is actually an uncomfortable and strange tale that is difficult to both tell and listen to, still awesome. It will just find its awesomeness in other ways at a later date, perhaps in its retelling.

The Coolest Disease Prevention Effort Ever

This is one of the coolest things I have ever heard of. Genetically engineering mosquitoes to fight Dengue fever.


Here's how it works. Scientists genetically engineered male mosquitoes with a genetic flaw that kills their offspring in the pupa stage. So they release the male mosquitoes, they mate with wild females who lay the eggs, and all the offspring die. The cool thing about killing at the pupa stage is that the hatched eggs still go through the larvae stage and compete for food with the wild larvae thus preventing even more mosquitoes.

I know what you are wondering. How do they grow the mature mosquitoes with the genetic flaw? They added a gene that knocks out the genetic flaw if the larvae are raised in water containing tetracycline. That is just fucking cool.

The article I read states that there are many advantages to this approach:
"This system has several attractive features. First, since it is only males who carry these genes, no one will be bitten by genetically engineered mosquitoes. Second, because the gene construct is lethal, it shouldn’t spread into the wild mosquito population — instead, it should eliminate it. Third, the fact that the gene is lethal at the pupal stage means that fewer engineered mosquitoes need to be released. Finally, in a traditional control program, the hardest part is finding the last of the animals you seek to eradicate; in programs of this kind, the males will do it for you. Males, after all, have evolved to be good at detecting females."

Here is the whole thing:
http://judson.blogs.nytimes.com/2008/09/09/a-genetically-engineered-swat/index.html

I hate sodium hydride

I just set up a relatively large reaction (~1.5 mol) using, you guessed it, NaH. Of course I tried it on smaller scale. Of course I'm trying to both bring through material and improve on the existing methods. Unfortunately the preliminary work I had done was a little capricious, so in the interests of time I retunred to good 'ol sodium hydride. I had gotten everything into the flask, I had added all my reactants, I had added a catalytic amount of ethanol to initiate the reaction, I had monitored the gas evolution, and I had even kept a big bowl of ice water handy to cool if necessary.

Everything was going swimmingly, and as I had hoped and expected. After all the reagents were in the flask and gas evolution had dropped significantly, I started to heat for the second stage two hour reflux, and guess what happened.

I've already spent about 2 hours cleaning things that were in my hood like some of the glass that was nearby, and a stirplate. Tomorrow will be the cleaning of the hood itself, and salvaging the last of that reaction. If I'm lucky I'll be able to reassemble my manifold the next day and install it, then I'll be up and running to work all weekend to try to catch up.

Yay chemistry! Yay sodium hydride!

At least no one was hurt.

more great NM food

For my trip to Austin, when I saw the Toadies show, my hot and awesome girlfriend got some fresh roasted Hatch green chile. Typically the harvest comes in around August/September, and everyone who loves to cook with it in New Mexico gets a bag (35 lbs), has it roasted, and freezes a bunch to use throughout the year until the next harvest. Around this time of year is is plentiful and cheap in NM, but not most other places. In recent years HEB grocery stores and Central Market have been carrying it in Austin, at greatly inflated rates by NM standards, making it much easier to get for NM expats living there. Out here in the mid-atlantic, however, still hard to come by, which is why I was so amped when my rad lady procured chile for my visit.


Here's what I did with the green chile, and also how I made the carne adovada for Dr. Miller's edification.

Green chile sauce/stew:
This is a very common stew style sauce in NM for putting on everything and anything. Like most important, regional sauces there are shitloads of ways to make it. This is how I did it last week.

1. Sweat an onion in vegetable oil in a pot. Olive oil would work, but flavorless is better in this case.
2. Brown cubed pork loin with onion.
3. Near end of browning add crushed garlic. I like a lot of garlic, and this was a medium-large pot that I wanted to fill about 2/3 of the way full, so I used a whole bulb.
4. Add about 2 cups of roasted, peeled, seeded, and chopped Hatch green chile.
5. After the chile has had a chance for the flavor and aroma to open up a bit add liquid to cover. I used a can of beef stock and water. Chicken would have been more appropriate, but the beef was on hand. Simmer until the pork is almost cooked to desired tnederness.
6. Add cubed potato. The potato will thicken the sauce slightly, without making into a gravy like consistency. If you prefer you can add flour to the sweat instead, just go light. Simmer until the pork and potatoes are tender
7. Right at the end I added a peeled, seeded, and sliced tomato, and removed the pot from heat.

At that point it was ready to go and I ate some over rice, and put the rest of it up. The next day I separated it into zip top bags and froze them to be used later.

Carne adovada:
I've made things like this before, but this time had some modifications I like, and the product was fucking awesome. Unless someone comes up with better shit this is going to be the way I do it from now on.

I got a pork shoulder, cause I'm a cheap bastard, and broke it down myself. This is kind of a pain in the ass, and a good place to save time and effort if you feel like spending a bit more. The meat just needs to be collagen laden and good for long, slow cooking. Actually it is a huge pain in the ass, especially if you don't do it periodically, and I would recommend against it unless you just want to try it once to see.

Cut the pork into large chunks. My mom and I refer to them as fist sized, but in reality they are smaller than the fist my gangly mitts make. You want the smallest ones to be larger than a golfball, and the biggest smaller than a softball. Simmer the pork in just enough water to cover with a lot of garlic powder, and some black pepper.

I've tossed the bone in before too, but it didn't add much. You could reserve the stock and use it for the chile, but I think that the chile made that way isn't the best for this dish, even though it's pretty damn good.

Simmer until the pork is tender and comes apart easily, cool and store if not finishing the dish right then.

The chile was made essentially following the directions on the package. You can make red chile without NM red chile powder, but I think it's really best with the right shit. Just don't ever use "chili powder", that little i can fuck up a lot of your work. I made a roux with olive oil because I found out at an inopportune moment that we were out of vegetable oil. It was pretty tight, so I softened it up a bit with more oil and some lard I skimmed off the top of the cooled pork, and took it a little past blond. Strictly speaking a white roux is what your'e after, but I have a lot of trouble not fucking with things I'm working on so I went a bit further. I added the chile powder, cooked for a minute, added water (out of chicken stock), garlic, and pepper. Cooked it for about 20 minutes and was rewarded with an incredibly thick sauce. I purposely made it thick to ease storage, but this was impressive. It was essentially red chile pudding, and even cracked deeply upon cooling. Cool and store if not finishing the dish right then.

I pulled the pork chunks apart to make smaller chunks. I could have just as easily cut them up, but I wanted to go over them one more time to remove fat and grisle. Another reason not to break down your own pork shoulder. If you suck at it, like me, it makes extra work for you on more than one occasion. I put the pork in a pot, added chile and water to make the consistency I wanted and just cover the pork, and simmered until the flavors combined.

Completely fucking awesome, melt in your mouth pork, and a nice, smoky, flavorful sauce with a touch of heat.

I poached a couple of eggs and plopped them right down on top of a bowl of that shit, and it fucking ruled.

rock 'n roll

If you get the chance to see the Toadies on their current tour, or any tour for that matter, you should. Completely bad ass.




This song is completely awesome and is one of my personal favorites not only because it's so good, but also it had heavy radio rotation even with it's very strong negative content and imagery. I think this is one of those cases where someone thought it would be "pretty" or "poppy" and played it without really listening to it first.

If you don't know what it's about, listen to the lyrics. Should be pretty self explanatory.


edit: This was at Stubb's in Austin, to answer Dr. Miller's query. These guys are so well liked that after they sold out this show well before the show date (Stubb's can hold about 2,200 people), they added two more shows to make it three nights in a row, and then sold those out too. Like I said, completely bad ass.

ACS

I went to the ACS national meeting the week before last. It's always nice to get to go see some old friends, schmooze, and get all loaded. Sometimes you even see som new chem, although thats pretty uncommon these days. For example I saw McMillan and was really impressed until a day later I was recalling what I had seen. Then I realized that the guy has built an awesome career one a couple of iminium reactions. They are great reactions and all, but still.

I got to see Nicolaou give a retrospective as well, and it was not nearly as motion sickness inducing as I had hoped it would be. The slides for first half of the talk was taken directly from his Tetrahedron prize talk, which are horrid slides, but I'm inured to them after having seen them already. The slides for the second half were taken directly from his new book, and while pretty garish, they were really not too bad by his standards.

I haven't been to a national meeting poster session in quite a while. Typically the poster sessions are where the best stuff is, so you shouldn't miss them, but I've skipped/missed them or not gone to the national ACS in almost 10 years. This time I made extra effort to see as many of the poster sessions as I could, and saw some stuff that was new to me. Unfortunately the newness was not good newness.

The first thing I saw as not really new, but drove a point home. Most of the medicinal chemistry, which is of course is old and dead if it's being shown, was boring and looked like the kind of shit that would be looked at as a punishment project by many chemists I know. Even better or worse depending on your viewpoint was the throngs of people who were walking from one poster to the next taking pictures of them all. One aisle even had several in a row from a big pharma company that had little printed signs at the bottom that said no pictures.

I don't really know what's worse; crap chem, the desire to copy crap chem, the desire to protect crap chem, the fact that a little piece of paper is expected to protect the crap chem. Interestingly these particular posters were not manned when I was there, leaving the 8.5 x 11 sheet of protection as the last line of defense.

I think I'm going to spend a little more time investigating positions in process and academics.

comfort food

I'm from New Mexico originally, and like most everywhere else the food there is specific in a way that people from there can easily see but people from other places think is the same as any old 'mex you can get. Belittling New Mexican food or comparing it to different mexican food (read inferior) will start an argument with a native New Mexican more easily than discussing how to properly chromatograph a compound will get a dry vs. wet pack argument going among organic chemists. I think it goes back to fond memories of childhood, and the things that go along with it. That and the desire to tell some shithead just how wrong he is.

In any case every locale has it's own comfort food, and when you are as far from a good source of your own comfort foods as I am, sometimes you have to break down and make it yourself. From scratch. Recently I went to the effort to make some carne adovada, and I used a lovely bag of ground red chile from Chimayo that my folks gave me a while back.

It was a pretty long and drawn out process, mostly due to the fact I couldn't work on it for the time needed several nights in a row. From start to finish took 3 periods in the kitchen for between 1 and 3 hours each, with breaks of course, over the course of about a week. My effort payed off with most of a gallon of carne, and a spare quart of extra thick red chile sauce for later.

I gotta say it rules, and was worth every bit of effort. Maybe next time I'll blow off breaking down a pork shoulder myself, and buy some pre-prepared pussy bullshit, but for this time it had to be right. It has made three or four of the best meals I've had in months. Awesome.

New Mexican food rules.

the most pleasant auto accident I've ever been in

I got into the mildest wreck I've ever been in late last night, while coming home from work on my motorcycle.

I was sitting still, waiting on a light to change, and there was this thunk. It was sorta odd and confusing, and louder than it was jarring. I had gotten pushed forwards a bit, and I think I accidentally dumped the clutch as the bike sorta slid forwards some more while I turned to glower at whoever was behind me. I got off and inspected the damage, which was minimal, and looked up to see both the driver and passenger hadn't moved. I'm pretty sure the guys hands were still at 2 and 10. I walked over and noticed something wrong with the drivers lip as I got closer. It looked like he had smashed it and it swelled to gross proportions. For just a second I thought he might have hit it on the steering wheel, but I realized it was such a small accident there was no way, and it wouldn't have swelled like that in an hour, let alone a few moments.
I got to the side of the car, and figuring only a drunk would hit a stopped vehicle at midnight, I was rewarded with a drunk.

He had a chew in that was so big it looked like he had a shit-covered golf ball in his lip. When I got there all he said was "Is it all right?". I didn't have a real answer for that, not expecting that particular version of the post wreck question. I mumbled yes while trying to think of some damaged part, but as I reexamined the scene the miraculous truth was no. The license plate
got pretty bent up under the tail, and there was a bit of a mark on the underside of the muffler but thats about it. Oddly his car had some gouging on the hood where my muffler had scraped up it, and the bumper might have been damaged, but who can tell on a shitbox like that in the dark.

insert car here

I wasn't hurt, and the bike was ok, and I was way tired so I just wanted out. I got the dudes name and number, checked his license to make sure the name was real (which took a while for him to produce in his state), and split.

I felt a little bad letting a lush right back out onto the road, but fuck it. After an accident if he didn't pay more attention he's probably destined for a fatal single car accident on the way home.

my balls

Liam and I went to Adams Morgan yesterday to get some food and drinks, and we took the Metro there so we could get trashed and not have to drive back. Not to mention that finding parking in Adams Morgan is a complete pain in the ass.

When we got off the train we gave a check to see if the tennis ball was still there. We found it a hundred or so feet further down from it's initial deposition spot, slowly making its way further into the heart of our nations great capitol. Interestingly there was another tennis ball right near it. Maybe my drunken stupidity was entertaining enough that someone else wanted to try my daring feat.

punk rock?

Last week I went to see an Alkaline Trio show at Ram's Head Live in Baltimore.

I'm a pretty big fan of them, but have only seen them at a relatively short SXSW show and had never seen a show at Ram's Head Live, so I was pretty excited leading up to it. They aren't exactly a punk act, but for lack of a better term, and the fact that a lot of punks seem to like them, they get labeled as such and often treated as such too.

Punk fans can be a funny lot, and being a sellout is typically seen as one of the worst things a band can do. However since many modern punk losers shop at places like Hot Topic I feel like them calling a professional act a sellout without really knowing the whole story pretty laughable. It seems that there are some groups calling Alkaline Trio sellouts these days.

A few days before the show I was surfing the net and decided to look into what they had been up to in recent years, and saw some random whining from fans and promptly ignored it. It seemed that the Trio had signed to a major label for this years' record. I could really give a shit, one way or the other and it seemed reasonable after their two previous albums (both on Vagrant Records) had managed to make it into the Billboard top 25.

On their own site I a reference to them playing 'Zumiez events', and looked into it out of curiosity. The Zumiez Couch Tour seems to be a free skate and music deal that did about 10 dates in the spring/summer. At malls. I knew something was wrong, but it was so odd it took me a while to figure out what was going on. They did free shows at malls. They did a mall tour, not unlike Tiffany or any of a number of boy bands. I was pretty stumped by that, I must say.

Reading more on their site they apparently have a new shoe out too. I thought that was odd, but the thing that really got me was it's by Nike. That's a whole new level of strangeness for me when it comes to a band. Alkaline Trio-Nike shoes? Really?

The shoes are a limited edition, and there are messenger bags too that were available first only at one store in Huntington Beach. There is even a video about the making of them. I watched it, hoping it would shed some light on this very odd (to me) situation.

It starts with some scenes of the lead singer Matt Skiba surfing, and then goes on to show him later describing the process of getting the shoes designed and made. The shoes are red and black supposedly because they are a Chicago band and love the Bulls so much. Surfing, Huntington, Chicago. Sure I see how direct that connection is. Why not.

There were none of the other band members present, there are two more if you are unsure what the titular Trio was referring to, so it was all Matt all the time. He said that they were bike messengers when they met and started the band, so there are tire tread graphics on the shoe. I believe the founding members of Alkaline Trio were all bike messengers, but Matt has been the only one left since 2000. I have no idea if the other guys like bicycles or not, but that seemed a little odd to me.

I don't suppose it helped the whole presentation much that during the filming of the vignette Matt, who I had always thought was a great songwriter with interesting lyrics, sounded just like a dumb band guy.

In any case we went down to the show with high hopes to see some good music from poorly spoken sellouts on Friday evening. The area around the venue was a nice parkway type shopping/food/bar area that was all fenced off for the weekend with guys carding to get in. There was an open air stage with a mediocre cover band for free, and bars outside as well at the established ones along the sides. It looked really cool, but we had to get to the show.

Once we finally got inside and found out that we were more or less on time with our planned schedule we got some drinks and checked the bar out. That place was AWESOME. I'm not sure, but design wise it was the best, or very nearly the best place to see a show I've even been to. It was very open so you didn't get too crowded or claustrophobic. It had seating right at the front by the windows, that was way away from the stage but had flat screen TVs to watch if you wanted to relax. Almost everywhere else in the entire place had some sort of view of the stage. The first floor more or less surrounded the stage on three sides, and there was a second floor that was all open so you could see the stage from almost all of it including the bleacher type area in the back. There were even some catwalks as a faux third floor to see the stage from up high. There were bars on all three sides on the first and second floors, so it was hard to get more than 100 feet from a cold beverage. There was even a pizza joint on the second floor with more TVs so you could watch the show while eating.

Probably my only gripe with the place was the charges added to the ticket. I hate it when venues add charges to tickets that can't be avoided. To me those should be part of the ticket price. It's not a $17 dollar show, it's a $22 show. I mean if they are going to charge me $2 for ME to print MY tickets, how is that not part of the service charge? The service charge that shouldn't even exist. Fuckers.

The show was pretty good, and it looked like a sold out crowd. I was pretty entertained by how much Mat Skiba on stage reminded me of an evil Neal Patrick Harris.

Matt

Neal

Had some drinks, saw some rock, and still had time to stop off at Asylum for more drinks on the way home. All in all a good time. Except for those fucking service charges, anyway.

happy 4th

Liam and I went down to see the fireworks tonight in DC. They have one of the best displays in the country, if not the best. You wouldn't know by asking us, as it turns out.

We took the metro there, cause driving to an event like this is retarded. We aimed to get there right about the time it started to not have to stand around waiting for the goods. We figured we would just walk up Constitution ave. like I did last year, instead of waiting in all the crowds.

Everything followed this plan until I decided I needed a cup of coffee, and Liam needed to pee. We stopped at a Starbucks, because even though they suck, they are convenient. We had plenty of time for the side trip. We had plenty of time to wait for the coffee, which actually didn't take long at all. As it turns out we didn't have enough time to wait in the bathroom line.

We exited the coffee shoppe and basically heard the fireworks come to an end. I joked about how hilarious it would be if we had missed it. We had missed it. While it was very funny, it wasn't as funny as I had joked about seconds before.


We made our way back to the Metro, with a huge fucking wall of people about a block behind us, and actually got a seat to go to Adams Morgan. Oddly when we got to the Adams Morgan stop, I realized it was the first time I had been there since I beaned a random schmuck with a tennis ball. We looked in the track for a ball and found this one (sorry for the poor quality phone pic):



Looks like our ball, but who knows. Great sanitation job WMATA, why don't you spend a little more time cleaning up after my ass.

pyrotechnicality

The cover story for the newest C&EN is green fireworks. The first thing I thought of when I saw it was "that's stupid", but after reading it I see that there may be a use for less smoky and toxic fireworks. Some of our LANL brethren even started a business based on them.

I bet green fireworks will have very little benefit for the delinquents who, like me as a youth, use them for wonderful non-intended things like destroying insect populations with explosions and hellfire. Not to mention how much dangerous exciting fun it was purposely misusing them. It's surprising how entertaining it is to shoot bottle rockets out of your hands into a ditch, or throw them at each other when your 12. Well, any age, really. There's nothing quite so exciting as taking something thats obviously dangerous and very cheaply made and significantly modifying it for increased danger. All you need is alcohol to complete the fun.

As I fondly think back I don't believe less smoke would have been much of a benefit in light of the piles of corpses, paper, and ash we left behind.

I like it with bourbon

Saw this at the grocery store tonight:

more journals please

I went in for a few hours earlier and tried to catch up on my reading a bit.



I think the only thing I still like about paper journals more than online is that if they weren't piled up in my way, I wouldn't keep up with them all.

the joys of public transportation

I went out drinking last night in Adams Morgan, and, as is often the case, me and my buddy took the metro to get there and back. No drunk driving, and no parking woes; you gotta love it.

I had too much to drink, again often the case, and on the way back to the train my buddy found a random tennis ball. While we were on the platform waiting for out train to arrive he was joking about bouncing the ball off the wall on the far side of the track and catching it, but wasn't going to actually do it. While they don't usually hassle patrons, the fines for fucking around are pretty high, and a cab ride back from there home would probably be at least $30-40.

I was egging him on to do it, and when the train was coming so I tried adding some excitement and urgency by counting down his window of opportunity until the front of the train was even with us. He, of course, ignored all this. Most likely due to his intelligence and lack of severe drunken stupor.

As the train slowed to a halt in front of us I had a random flash of stupidity I mistook for brilliance. While I wouldn't have been able to appropriately voice my idea in my state, I had this ridiculous internal dialog going on: "I'LL take the ball, throw it OVER the train and catch it! With my obviously superior science skill I'll be able to accurately deflect it off the curved wall right back into my waiting hands. All in attendance will be entertained at my pithy display of bravado and skill!"

With a narrow window of opportunity I asked for the ball, which he inexplicably gave to me. I "carefully gauged" the throw probably making a number of errors, and made my move. With all the finesse of a limp-wristed mathlete I lobbed the ball at the wall and it rebounded, as you might expect, well off it's mark in a decidedly downward trajectory and bounced crisply off the head of a passenger exiting the train right at that moment. The chances of me catching the ball if it had come right to me were slim, and after the bounce off the poor schmuck's head - nil. The ball bounced and rolled its way across the platform, and fell into the opposite track. I beat a hasty retreat onto the train mumbling an apology to the aforementioned schmuck who seemed nonplussed by the whole ordeal. I expect he was as inebriated as I was.

In the end I did manage to entertain a number of onlookers, but more for my buffoonery than bravado. Like they say, there is no such thing as bad press.

gay brains vs straight brains

Here is a Time article covering what looks like a neat study.

What the Gay Brain Looks Like

Apparently gay dudes' brains have similar hemisphere symmetry to straight women, and gay womens' have similar symmetry to straight men.

I suppose the big question is that once you pray-away-the-gay does your brain revert to normal/non-homo symmetry?

yay, high school!

One of Dr. Miller's cohorts talked on Friday about his upcoming HS reunion, and it reminded me of mine. Well, the lack of it, actually. So I'm going to totally bite off of his style and talk about it too.

I graduated in '90, and was glad it was over with just like most everyone else. The dude who was the class historian, Sean, was a good friend of mine and a real stand up guy. He was however a decent bullshit artist and not a really an academic/brown noser type. I think he signed up for the office just for the resume fodder, and never really planned on doing the various stupid duties that came with it. Who can blame him, class historian, what a joke. So the 10 year anniversary of all our departures came and went with no mention of the reunion at all, which I really didn't care one way or the other about. One of our central friends always threw a great xmas party that was well attended by the old group, so that was a better way to keep in touch anyway.

That winter I went home for the holidays and went to the xmas party, and ran into an old friend who told me she went to the reunion. I was pretty confused how she could have, and made her explain the whole deal to me.

Apparently one of the academic/brown noser types figured there was going to be no official reunion and organized one herself. I don't really understand why one would do such a thing, but my guess is she just wanted to get a few old friends together and grab some drinks. Thats fine, but why not just get a few old friends together and grab some drinks.?Why call it some sort of pseudo-official function that brings dread to so many?

Anyway, the event was thrown together sorta quick and not too many people were invited. It was held at a bar that was a bad idea in and of itself. There used to be this really huge shitkicker bar that could hold something like 1000 drunk cowboy wannabees. Oddly Sean had worked security at the place in the past and it sounded like a nightmare, as you might expect. In one corner of this shithole was a 'nightclub' with velvet rope, dress code, and everything. Seems like the later 90s was the time for bad club ideas to filter from the coasts into the heartland, and someone decided that these two opposing terrible ideas spelled gold when put in the same space.

The resultant reunion party turned out to be only girls, 5-10 of them, in one group going into hicksville for cocktails. If my recollection is correct the evening consisted of a little bit of shouted chit-chat, a lot of turning dudes down, and an early night.

I'm pretty glad I missed my 'reunion'.

Climbing Pikes Peak

Last tuesday, we decided to ditch work and climb Pikes Peak (14,110 ft) the cool way.  The Y-Couloir.  1000 ft of steep snow to the summit.  We kind of cheated to get there.  We drove up to 13,000 ft on the road that goes to the top and traversed over to the climb.  

  

Next task was climbing the well packed 45 degree snow slope.  I was excited about using my crampons and ice axe on my first coulior climb.

The picture above is the view down and the picture below is the view up.

Around 13,500 ft I slowed quite a bit due to the altitude.  The views made the rests worthwhile.

At last the summit was in sight.  Below is a photo of Brandon at the top and Aaron and I on the last bit of the climb.  

like a kid again

Last night I went to see the Breeders play at the 9:30 Club. It was a pretty sweet show, and better than the last one I saw where they just sort of split after 20-30 minutes without finishing their set.

I was feeling pretty good, and felt like I was recapturing a bit of my youth when some chick in the vicinities perfume came wafting by. It happened to be a perfume that I must have smelled before, circa 1993-94, when I was really into the breeders and indie chicks. The combo of smell response and loud music (I was a little too close to the speakers) really threw me for a trip, and I felt like it actually was 1993-94 for a minute.

I ended up having a great time and drinking too much, so much so that when I was stumbling out of the house this morning to come in to the lab I dropped my motorcycle while trying to maneuver it out of a tight spot. Now my hangover has slowed my workday to an almost complete halt.

So much for feeling young.

the joys of undergraduate chem. classes

I stumbled across this the other day:Momentarily I was transported back to the joys of grading 50 lb stacks of exams, and thought about how much I used to like to find wacky or unusual shit in there. It was always interesting, although not always fun, to see really unexpected stuff. I would have loved it if someone had done something as creative as this, especially if they had done as well as this guy did.

the computer - useful for something other than chatting with teenage girls that are actually middle age dudes

I was just organizing my crazy selection of journal articles on my computer, and for the fuck of it I checked to see how much drive space it was taking up. Right now it is just over 800 mb of chemistry goodness in pdf form. There has got to be close to 10 years of crap I've read and wanted to keep for some rainy day or other, both random and researched, in there.

Makes me damned glad I switched from paper to pdf. I don't even want to think about what a drag it would have been to try to sort through and move all that shit halfway across the country. Last year when I finished up my thesis and packed my desk to move I got into the frame of mind a great many people do, and threw out anything I didn't feel like carrying down to the car. I expect that up until a few short years ago, and still now for people who are fond of reading on paper vs. a monitor, a lot of good references got tossed in the name of convenience when moving day loomed near.

Luckily with a computer large amounts of pdf files and pornography don't add any mass at all, and the stuff on the computer ended up coming through unscathed. Of course that has more to do with my being too lazy to cull it than with any actual attempt at efficiency.

Perhaps the craziest part of all is that it's almost all organized. Anyone who knows me or has ever seen my bench would probably freak at how well I've managed to keep order over all that crap.

don't let this be you

I had this lovely discussion with a coworker the other day. She's a nice post doc in a group made almost entirely of post docs like myself, but I really didn't expect work like this from someone who finished grad school.

She comes up to me with a reaction scheme from our boss' current project and asks me about a step in it; a nice McKlusky N-demethylation. Well 2 steps, really. [Shameless plug: if you need or want a name reaction book get this one. It's from my friend Bert, it's almost 3000 pages long, it's a searchable pdf, and it's only $40.] Anyway I could tell by the way she was asking she wasn't interested in generalities, I guessed, correctly, she had tried it and it worked poorly.
She asks a few questions about it, and it was obvious she didn't know how the reaction worked. Not that you need to know how everything works, but if it is an important reaction it won't kill you to spend a few minutes to figure out what the hell is going on. I guess I'd call this mistake #1.

She said she had found a good prep, I didn't ask what her definition of 'good' was, but that it involved carrying on the intermediate crude to the second step. She did this, which is fine, but she didn't take an NMR along the way to see if the demethylation/carbamate formation had worked. Mistake #2.

So at this point it's obvious it didn't go well, and she tells me there is no demethylation and the starting material is all gone. I'm trying to remember her structure and thinking of things that could go wrong. In my poor recollection of her target I can see one really obvious problem with the reaction as a choice which she totally missed due to her lack of understanding of the reaction mechanism. I'm telling her how it works and asking if she talked to the boss about the reaction. She hadn't. Mistake #3.

I know many people wouldn't talk to their boss about day to day stuff, and I know I would have not liked to talk to my old PI about any routine stuff unless I felt like getting raked over the coals about various and sundry horseshit, but our boss here is very different. He is an exceptionally cool guy, and the only thing he like more than doing chemistry is talking about chemistry. And maybe drinking wine. His reaction scheme was the source of the idea in the first place, lots of our targets share route details like the mid to late stage McKlusky, and he has lots and lots of experience with both her class of compounds AND the McKlusky/von Braun type demethylations. Who wouldn't spend the less than 5 min asking him if he thought it would work, especially if he could say "we tried that on a really similar substrate and it did/didn't work"?

I next asked her what she thought the product was, just to see if my suspicions about the side reaction were correct, and she told me she didn't really know. She had just looked for the N-methyl, saw it, and realized she was boned. I tried to get her to talk to the boss and she didn't want to until she did more reactions, which is a little silly, but whatever. She asked me about the next set of conditions she was going to try, and I tried to come up with some helpful ideas but she said she didn't have enough material to do too many trials. I figured she must be near the end of her route if she was doing the demethylation, so I wasn't to surprised, but the reason she didn't have the material was because she bombed all her material through the step! She put 500 mg of advanced material into a reaction she had never done, and didn't understand! That's only mistake #4, but the rest sort of don't matter in comparison. Really it's mistake #1 and the rest should all be pushed back into the background. I mean, shit, 500 fucking mg! Damn! There were times I would have done many evil things to get 500 mg of advanced materials, and would hoard and covet every single milligram. Fucking hell!

It was all I could do to not look shocked, cough, and splutter. She was already painfully aware of how much that little trip to the hood had cost her in terms of time and effort, and I didn't really feel like she wanted any "you should have ..." crap.

She still doesn't want to talk to the boss, and managed to find a mg or two to try another set of conditions today that she checked after the first rxn this time (the N-Me is gone this time if anyone is interested), but she is still going to have to go back a ways to come up with some material.

I guess we all have bad days, and I expect she won't fuck up quite this badly for a while. I sure know I won't do anything like that. Sometimes it's nice to be other peoples sounding board (aka emotional tampon) to be reminded of how bad shit can go if you aren't paying enough attention, not to mention the fact that it's always nice to NOT be the one dropping the ball.

Bear Hunting

I have never been much of a hunter, but when I mentioned to my gun nut uncle that Stephanie's grandfather goes bear hunting, I was cajoled in to planning a hunting trip in the Bitterroot mountains of northern Idaho.   Grandpa Dick shot a bear on the first full day we were there. 

My Uncle on the right and Grandpa "deadeye" Dick on the left

My favorite part of the picture is the tongue hanging out in a cartoonesque kind of way.  Next task was skinning the bear since my uncle wanted to make a bear rug out of the hide.

Can you guess the sex?

Here is the finished product.  Enjoy! 

organic chemists are indeed lazy

No shit chemists are lazy, I found an error today in Org Lett that actually surprised me a little.
Papers are always peppered with mistakes, sometimes liberally, but I feel like some things shouldn't get fucked up. These guys made a natural product, Sanguiin H-5 with a nice axial chiral center. Here is the natty-P from the graphical abstract with a strategic bond highlighted, and the final structure of the final scheme.






The two were obviously were drawn differently which really makes no sense, but is mainly an issue with picky people like me, and there is a relatively major error in the final product drawing. Can you find it? It's not the little S in parentheses either.

I always wonder why people don't proof read their shit a little better. After who knows how much effort went into making a molecule the paper shouldn't be a hack job just to get it out. A missing punctuation mark or reagent is no big deal, but the final structure REALLY should match the target a little better.

Now I guess I should stop being lazy and get back to the bench.

organic chemists are REALLY lazy

Newsflash! Organic chemists are lazy. While many organic chemists work long hours, it turns out that a new analysis of all organic compounds reported to the Chemical Abstract Service shows that we are intellectually a bunch of slackers.

http://pubs.acs.org/cgi-bin/asap.cgi/joceah/asap/pdf/jo8001276.pdf

The authors found that 35.7% of the 33 million organic compounds ever reported in the chemical literature have one of just 30 framework shapes. Also, 32.3% have one of the top 20 shapes and 26.1% have one of the top 10 shapes. So over a quarter of all the compounds ever reported in the chemical literature have one of 10 different shapes.

What the hell is a framework shape? Well, each of the 30 structures above is one framework shape. Each carbon atom can be substituted for any other heteroatom and each bond can be single, double, or triple. Also, all side chains are ignored. So scaffold 1 encompasses not only cyclohexane, but also piperidine, benzene, pyridine, morpholine, toluene, phenol, 2,6-lutidine, etc. No wonder 2.3 million compounds have that framework shape.

So all you chemists out there, get off your asses and start making some new structures.

Cockpits! Booby Traps!

I'm watching the first season of the Venture Brothers on DVD, and I have to say that this shit rules. You can't go wrong with anything that has James Urbaniak and is on Adult Swim. Adult Swim is probably the best network on TV right now with actual writing and new ideas. Well, mostly anyway.
Perhaps the best part is the commentary tracks where Jackson Publick and Doc Hammer basically talk about whatever they want, which is usually funny as hell, and not odd comparisons between the characters and their real life experiences that supposedly prepare them for their work.
After watching No Country for Old Men, I watched the extras and I felt little interest in Josh Brolin, aka big brother "Brand" from The Goonies and son of actor James Brolin, saying he was good in his role cause he worked hard on a ranch.

first

Yet another blog.