TMI Thursday: Commando Operations

Ever since I've had my gall bladder removed, I've suffered from something that I refer to as "post rectal drip". See, sometimes, if I've had one of those shits where things have been good and loose, a couple hours later I'll develop that "not so fresh feeling" at the back door. I usually go, clean up, and then everything is okay for another couple of hours. The big problem is, when I can't get away, then the insides of my ass cheeks tend to chafe, which is an all new definition of the phrase "pain in the ass." Now, this also happens sometimes if I'm suffering from a good bout of ass sweat, but the ass sweat chafing pales in comparison to the post-rectal drip chafing.

So, about a year and a half ago, I decided that I was going to get healthy. I was going to shed some weight, increase my stamina (heh heh heh...), and overall have a more healthy body. The best way, I figured, was to take up jogging. Now, I love jogging/running. I really do. You wouldn't think it to look at me, but buried beneath the layers of blubber is a runner at heart. However, as it had been many moon since I had last endeavored to jog, I figured I should work into this. I'd start slow and hopefully be able to sustain some form of stamina that would let me jog with some regularity.

To that end, I started walking. During my lunch hour, I would walk a course by the lab building that was about two and a half miles. I could get it done in around 50 minutes, if I didn't drag my ass. As all good ideas of this ilk begin, I started this regimen in January.

Long about the end of April, I was getting pretty good at this. I had lost at least two belt sizes and I was slowly getting to the point where I felt comfortable with attempting to jog. However, I wasn't dressed properly, so I began bringing in shorts and a t-shirt that I could change into prior to exercising then change back out of in order to perform my usual daily work in the lab, hopefully sans the funk of a sweaty man hanging about me.

The other thing is that, toward the end of April, it was getting warm 'round these here parts. Now, the scene is set. One day, I was out doing my lunchtime walk when, around the one mile mark, I sense a little leakage in the outback. At this point, I was at the apogee of my daily route--that is, the furthest from the lab possible in my little walk. Sucking it up like a man, I tried to quicken my pace so that I could get back to the lab and change as soon as humanly possible. Unfortunately, this had a dual affect. One, it caused my ass cheeks to rub together moreso than they were before, thus heightening the chafing. Two, it caused me to sweat more, and I could feel the tortuous trickle between my cheeks. Essentially, it was a perfect storm of ass chafing.

Finally, after my grueling pace took me to the point where I just wanted to fall down on my face and weep, I returned to the lab. As proof that God does, in fact, love me, my labmates were at lunch at the time, and so I was able to slip into the office, grab my stuff, and not have to let them smell what must certainly have been a case of Swamp Ass to the Extreme. I gathered up my clothes and slipped down to the restroom to clean up and to change.

Once I got there and dropped trou, I discovered that my boxer-briefs had gone to the point of no return. What once had been turquoise was now rendered an unholy mahogany, featuring an aroma fresh from the very bowels of hell, such that my nose hairs singed, my eyes watered, and my throat seized closed. Despite the lack of fresh air, I managed to clean myself up. Now, I had a change of pants. I had a change of shirt. I did not have a change of underwear. And I certainly was not going to pull those back up around my nethers after having freshly cleaned them. What was I to do? The only course of action was to strip them off.

And so I did.

I was out there, Jerry, and I wasn't loving every minute of it!

Now, I realize that a number of you don't have scrotums. Let me just say that, for those of you without, the seams of blue jeans and the soft, velvety delicates of a man's anatomy are in no way compatible. The moment that I zipped, the joint where the legs of my pants and my crotch come together seized ahold of my wrinkly, crinkly bag of skin with the tenaciousness of a midwestern housewife on a Vera Bradley handbag. With my lower lip aquiver and unshed tears standing in my eyes, I now looked upon my soiled and defeated companion who had given his life so that my sack would not suffer the indignity of being cloven in twain by my pants. They say you never truly appreciate what you had until you lose it, and such it was with my underpants. Softly, I hummed taps in their memory.

But, what to do? I exited the stall, stiff-legged, and motored over to the wastebasket. Unfortunately, it was one of those wall units designed for the paper towels you use after you wash your hands. This was not a suitable final resting place for my knickers. So, I quickly washed my hands, rolled the fallen soldier up, and made my way back to the lab.

I thought briefly about stashing the underwear in my backpack, but I was afraid that the lingering air of Swamp Ass would give me away. I couldn't just drop them into a waste paper basket in either of the labs, as we tend to not throw much stuff away. So, I did the only thing I could possibly think to do: I slipped them into a plastic bag and hid them in one of the 55-gallon solid hazardous waste containers in the lab. I deftly moved a couple of bags of used filtering agents over the top of the bag containing my soiled smallclothes, put the lid on and sealed it.

I then tried to go about my normal daily routine. However, after about an hour, maybe two, of wandering around the lab and office with no underwear, I became painfully aware of the fact that my pants were trying their best to eat my balls, Chewbacca style. Finally, I could take no more and left early for the day. After a frantic ride home, I dashed upstairs, shed my pants, slipped on a fresh pair of boxer-briefs, and reveled in the wonderment of having my nuts cradled lovingly in the warm, accepting folds of gentle cotton. "I'll never underappreciate you again, underwear," I cooed down to them.

And I never have since. *pats self lovingly*


Does this not sate your thirst for awesome TMI stories? Then check out all the other glorious tales of things we probably shouldn't tell at LiLu's home for the staunchy raunchy, TMI Thursdays!

TMI Thursday: Two for Number Two

So, I've been mulling this over a bit. It's not that I don't have plenty of good, juicy TMI stories. I mean, you've been reading my blog for, what, a couple days now? You realize that there's pretty much nothing about me that says "whoa, too far, I'm not going there."

However, it has occurred to me (read: sunk in through my thick skull) that there are some things most likely better off not said. Mostly these involve times when I've been inside someone, particularly my wife. Along those same lines, since she reads this, I'm sure she doesn't want to know about what I did with my ex-girlfriend in her ancestral bedroom back home while her father was most likely lying in his own bed, hearing us through the walls, and fuming. So, with those types of stories culled from the broad scope of things that I've done in my life that involve bodily functions of one type or another, we're pretty much left with stories about shit.

And, that's what we have today. A shit story. However, I realized that it wasn't all that great of a story, by itself. It's kind of amusing and all, mostly because I'm a dumbass, but it's still nothing grand and glorious. So, I'm giving you two tales of the toilet for the price of one this week.

Oh, don't get too excited. The second one isn't all that great, either.

STORY THE FIRST:

Anyway, about nine months ago, I was at work, calmly synthesizing my little heart out when suddenly I got that heavy feeling 'round back that told me I better find a commode quick or else we'd have a chemical spill of sulfur hydrogen iodine and tellurium. Yes, I know, that's spells "SHITe". Eat me.

So, I strip off my gloves and labcoat and then proceed wander down the way to the sanctum sanctimonium where I spent the next fifteen minutes contemplating what I ate the night before that could produce a smell so pungent and foul that the paint had begun to peel from the walls and the floor tiles slowly curled on themselves. After relieving myself of approximately fifty-three pounds of corn-addled excretia, I turned to behold what I had created. It was anything but good. And worse, with my ass having raised from the seat, I popped the seal over the bowl, and thus I unleashed an unholy and foul nebula into the room that threatened to overwhelm all creatures great and small within a twenty foot radius. Quickly, I wiped, flushed, flushed again, and once more for good measure. With tears streaming down my cheeks from the redolence hanging thick and blue in the air, I washed hastily and dashed from the chamber of secrets, seeking asylum in my office.

It just so happened that mere moments later, a tornado warning was issued for our county.

One of the "severe weather shelters" for our building happens to be...the men's toilet. It also happens to be the nearest shelter for my lab and office suite.

I ran, screaming, from the lab, shoving small children and old women aside. A friend of mine, who worked and sat next to me, made straight for the nearest shelter. I, however, bolted down the hall to one of the back offices, which are also tornado shelters.

A few minutes passed and the tornado warning was lifted. We returned, safely, to our offices and labs. My friend, who had sought refuge in the crapper, asked me, "So, why didn't you come in there with the rest of us?"

Now, honestly, after the tornado rips the building asunder, they're going to look for survivors and corpses among the rubble. Do you really want to be found dead in the privy? No, neither do I. However, I felt this answer would not suffice, nor was it wholly true.

"Well, you see, I know what I did in there twenty minutes before the warning, and I sure as hell wasn't going back in there."

"Ah," said my friend, with a bit of a smile, "well, you'll be glad to know that the smell has cleared...mostly."

STORY THE SECOND:

We had a bit of an odor issue the other day at work.

And, no, smart guy, it wasn't me.

It was a chemical. Somehow, it had gotten loose, and this particular brand of chemical--called an isocyanide, if you must know--is particularly foul. If you can smell it. I, however, cannot. It gives you headaches and causes you to want to vomit and gives you a sore throat. Nasty bastard, to say the least.

Anyway, shortly after arriving at work the other day, the two cups of coffee I had downed while driving the kids to school struck my lower abdomen with a vengeance.

"Hmmmm...must be 9:30," I thought.

I ambled down to my happy place and sat there pondering the ways and the whiles of the world for a bit. Finally, after releasing two very large, very healthy brown trout back to their natural habitats, I cleaned myself, took my leave of the place, washed my hands, and returned to my lab. I sat for a while, checked my email, and then called my wife and spoke to her for about twenty minutes. After I hung up, I worked on my notebook for a bit and then decided that I was thirsty. Oblivious, the entire time, to the fact that my lab had been evacuated until further notice.
See, the order had come down that we were to leave the labs and offices whilst I was in there discussing the pricing options with a man about his big, brown horse. Fortunately, after thirty minutes, I decided to go get some water from the break room. There, I found my labmates and team members, chatting idly about the stink in the lab and how they had to evacuate.

"So glad you could join us," one of them said.

"For what, now?" asked I, joyfully filling my water bottle.

"The smell in the lab. They've told us not to go in until it's resolved."

"Oh," I replied, a tad nonplussed, "Jolly good then."

I joined them at the table, then, suddenly understanding the plight of Charlie-in-the-Box, grape jelly squirt gun, Spotted Elephant and the rest of the Misfit Toys.

Although, I'm fairly certain, given my location when the evac orders came down, even King Moonracer wouldn't have scooped me up and whisked me away to his island kingdom.

For other truly tasteless tales of tawdriness, check out LiLu's joint at Live It, Love It: TMI Thursday.

Six Word Saturday, the Second Coming

Okay, so I had some fun the last time I did this. But then, the last time I did this, I was talking about pie and blow jobs. How can you not have fun with that???

Anyway, today's six words:

I should have been a cowboy!

Back when I was in graduate school at Notre Dame, the very first reaction sequence I tried could be summed up in the words "epic fail". Nothing went right with the material I had made, and it was a simple reaction of adding a Grignard to an epoxide in the presence of a Lewis acid. Simple stuff, right (trust me, non-chemists, a monkey could do this shit).

Problem was...it never went.

I changed solvents (from anhydrous THF to THF from a still to THF run through our purification system); I changed the source of the Lewis acid (used three different bottles of copper(I) iodide from three different groups on the floor); I even remade the epoxide, thinking a different batch would help. Nothing. Still no product.

Now, for you non-chemists out there, a Grignard reagent is a kind of highly-reactive organometallic reagent, which means it mixes organics (carbon and such) with metals (bright and shiny and malleable) to give you something that will react wicked fast if you look at it cross-ways. That being said, you get a little water in there, and it all goes to hell. Fast. And being that northern Indiana in the summer is a bit...what's the word...*snaps fingers*...right, humid! A little bit of moist air and the bottle of vinyl Grignard you've got suddenly becomes magnesium-based sludge.

I suggested as much to my graduate school advisor. I know. The audacity of a first-year grad student saying "Maybe this highly reactive and water-sensitive reagent over here is the problem." My advisor insisted I was full of beans--or shit, take your pick--and gave me some different conditions to try, all using the same bottle of vinyl Grignard, all the while reminding me that what I was trying to do was a "literature reaction" (which, essentially, means that someone else has already figured this out, all I had to do was follow the recipe like a good monkey). Finally, after one of the last conditions still failed to yield the desired product, I closed my eyes, rested my head against the cool hood sash and said to myself (because everyone else in the lab was down at Happy Hour) "I should have been a cowboy..."

Yes, it was about that time that the Toby Keith song was popular, and if you've ever spent any amount of time in Northern Indiana, you'll know that country music is the aural poison of choice. Plus, I kind of liked Toby's sweet mullet.

To cap that off, I skipped work the next day (it was Saturday) and moved my stuff from my old, crappy apartment into the house I was sharing with three other guys. After moving, I was too tired to go to work, and--honestly--too pissed off with chemistry to worry about it. Unbeknownst to me, my advisor was in, running that exact reaction.

I came in Monday morning to find him standing near my hood. Figuring I was fired, he simply stated, "That bottle of Grignard is bad. Order new." And left. Vindicated, I ordered the new Grignard (actually, I ordered two, the bromide and the chloride). The reaction worked just fine after that.

Now, I don't want to give the impression that I dislike my job. I love my job. I love the people who work with me. I love the project I'm working on. I might not bust out of bed every morning like Spongebob screaming "I'm ready!", but I do hop out of bed and head off toward work and do my job with a big, dumb smile on my face.

However, every so often, a cascade of events affects me in the lab that goes so far beyond absurd that it thrusts itself deeply into the realm of situational comedy. This past week and a half has been one of those eras in my life. See, I've had this compound that we've really wanted to make, and I've made it. Problem is, it's not getting pure. And, I've tried everything. I tried traditional chromatographical ways of purifying it. Still dirty. I've tried recrystallization. Still dirty.
It might not be thermally stable, so I haven't tried sublimating and depositing it. Finally, I decided to work on the HPLC--essentially, a robot whose soul sole purpose in life is to purify compounds. Problem was...when I took my stuff up in methanol (a very polar solvent)...it didn't fully dissolve. Thinking that I would help it along with a few drops of DMSO (an even more polar solvent), my stuff suddenly crashed out of solution. Yes, I recrystallized my material with methanol/DMSO. My supervisor laughed and said, "Well, maybe we can get a paper out of that..." I took the polar solvents off and tried again. This time, however, I decided to see what would happen if I added water, since the HPLC uses water to purify the compounds.

My reaction essentially puked orange-white stuff onto the sides of the flask.

Heaving a heavy sigh, I shook my head, looked at my friend Joe, and simply said:

"I should have been a cowboy."

Fun with Acronyms

One of my company's favorite things to do is provide a safe working environment for its employees. You might think that a bit peculiar, unless you remember that--despite all the talk about publishing books--I am a chemist. Sometimes things in the lab can go boom, or better, issue forth red clouds of toxic vapor, especially if they're not monitored correctly.

Right now, we're having a bit of training about the dangers of handling hydrogen, because for all intents and purposes, hydrogenations are one of the most dangerous reactions we organic chemists do regularly. The problem with hydrogenations (bear with me, fellow organikers...the meat of the post is yet to come) is that hydrogen gas (H2) is extremely flammable. It's actually more flammable than gasoline (once it hits the right concentration in air) and it burns fast. I don't know if you any of you ever had to do the reaction in high school chemistry lab where you chuck a piece of zinc into hydrochloric acid and collect the H2 gas given off by the reaction in bottles. I did this in both college and high school, and both times had way too much fun listening to that keen little fwoop! sound that hydrogen made when you got the match near it. Ah, good times, good times.
Anyway, the flammability of hydrogen is just part of the problem. Hydrogen is small, so it leaks from pretty much any "sealed vessel. Hydrogen also travels pretty quickly, as it's so small. There's a whole other problem, too, with the hydrogenation reaction, and that is that it's not spontaneous. In other words, you need a catalyst. Think of a catalyst as something that makes it easier to do a process that would otherwise not go; if you need further allegory, think of a catalyst as acting like a half-dozen rum and cokes and the reaction being the clothes of the cute girl in the corner of the party. The clothes aren't coming off without the booze; the hydrogen's not going onto the molecule without the catalyst.Problem is, most of the catalysts are metals, but not just your regular metals, but activated metals. Think of the rum and cokes as suddenly changing to shots of vodka (now can we see why I don't teach chemistry?). Not only are the metals more reactive toward the hydrogen (and the molecule is question), but they're also more reactive toward oxygen in the air. The true joy is that, when these catalysts are exposed to air, they react with oxygen. As they react, they get hot. If they get too hot, they mingle with hydrogen and make fwooping noises. Or they flat out detonate, depending on how much hydrogen there is, how much solvent, all that good stuff.
As you can see, this can be a problem.

Thus, we have our little safety talk. It may be boring to sit through, but at the same time, it's something that we all need to think about, especially if we plan on continuing to do both hydrogenations and living at the same time.

Now, there's something else that organikers just love, and that's acronyms. I mean, seriously, we love them. Acronyms are like porn to chemists, but especially organic chemists. Seriously. We make acronyms out of our clubs (ACS) and our journals (JACS, JOC). We have such creative ones, too, like DEAD. And DIAD. And DIPEA/DIEA and TEA and DMF and DCM and if those don't tickle our fancy near enough, we start working abbreviations into the mix and create MeOH, AcOH, EtOH, EtCO2CH2CO2Et. Oh, my lips are tingling with the spiciness of this conversation!!!

So, it's no coincidence that the speaker today trotted out a brand new acronym that I had never heard of, called the Organic Reactions Catalysis Society.

That's right. ORCS.

I guess the really cool thing about ORCS is it's not just synthetic organic chemists, but it's a society that spans all walks of chemistry life. At the conference, you can listen to talks from people in food sciences, materials, organometallics, synthesis...all talking about the best ways to do things and any little hints and tricks that might help make life in the lab easier and, more importantly, safer.

And at the end of every conference, everyone gets together and beats the shit out of the Elves.

Warning: Fluff(y) Post Ahead

Sorry for the lack of reading material this week. I've been busy wrapping up my current project so that I can get all my stuffs moved to the other building and start my new project on Monday. What? You didn't know I was getting transferred? Yeah, I got transferred to a different department where I'll not be battling the wretched hordes of cancer everyday. No, instead, I'll be trying to fight the wretched neglected diseases that are afflicting sub-Saharan Africa. Yeah, it's something I can tell my mom about and she can brag to her church friends about me.

To that end, I promise to supply something other than fluff posts in the near future.

As busy as I've been, however, I haven't been too busy to read your blogs and sometimes comment on them. I've also not been too busy to not see shit like this: Shitty Cat Jewelry. I mean, seriously? C'mon. You're kidding, right? Who buys this crap? I mean, someone must be buying it, as they have a whole catalog of garbage. And more, who wears it? The broad in Carmel, IN should be campaigning against these sins against artistic endeavors rather than Victoria's Secrets models.

I mean, it's enough to make Wizard Cat gather together a posse and kick some ass. Right after the one on the right can figure out how to use his new tiny little arms.

Letter Never Sent

Sorry for the misnomer, but I had kind of a shitty day at work today. I've resolved to stop listening to other people and start doing synthesis the way I know how to do it, and if that requires a little lithium-halogen exchange, then sobeit. I'd rather work with pyrophorrics than bumblefuck around trying to guess my way through someone's ham-fisted attempts at explaining a procedure to me, be it written on paper or orally submitted. Wow, that was a touch cathartic. Anyway, to cope with my sadness, I'm listening to Reckoning by R.E.M. (yeah, I like R.E.M. Eat it!). Since it's R.E.M., it all sounds like a suicide note anyway. Like my rant, it's cathartic in it's own way. Listening to R.E.M. is like hanging with my friend Steve: no matter how shitty something seems, you can take comfort in the fact that someone else has it shittier than you.

The reason for this oh-so-joyous post is that I sent off my manuscript stuff. Not today, but yesterday. I was going to write about last night, but I got wrapped up in telling everyone about Fair Oaks, IN and so I got a touch sidetracked. When I went to mail everything off, I was careful to keep my papers neatly stashed away in a folder so that the torrential rains wouldn't mar the otherwise pristine copies of my cover letter, outline, prologue and first three chapters. For some reason, I was strangely calm when I sent it off. I wasn't the usual ball-of-nerves that I have been in the past when I send away some of my work. I'm sure that doesn't really mean anything, but I thought I'd share that part of the journey. Now, I sit and wait.

I did want to thank everyone for your kind words in the comments section. I know that it took me a whole week to make the "big" announcement, but I had two sick kids to deal with (they had the croup...yeah...my kids were diagnosed with a disease that contained "the" in the name...yech!) and my wife was reading through the parts that I wanted to submit to make sure there were no big, glaring errors (she did miss that I misspelled the name of one of the countries in my book...shame on her!). Again, thanks to everyone for the congrats. It made me feel good all over again.

Since my wife liked what she read (she told me this, several times...and each time I responded with "You're married to me. You have to like it; it's in the contract." This did not amuse her as much as it did me), she went ahead and read the rest of the story, making small grammatical corrections along the way. Which reminds me, she changed "courtesy" to "curtsy", and since I don't want to look like a ham-fisted hack (I've used ham-fisted twice in this post...), I need to change it back. Anyway, apparently the ending made her feel really good. Again, I told her that she had to like the ending and the book because we're married. Anyway. Here is perhaps the highest praise I've gotten so far (keep in mind the source, please):

"I liked the ending. It made me smile. It made me feel good." (beat) "The end of Harry Potter didn't make me feel good. Your book made me feel good."

Deuce.

This means that, with the potential for the Boar War to be published at some point in the foreseeable future, I had to get back on the writing gig and start working on King of Storms and finish the rereading and smoothing over of both Shadows and Thistles. So, yeah, I've started in with the typing monkey routine again.

Fare thee well, Final Fantasy XII. I hardly knew ye. If you ignore the 108 hours of you I've played...

A Petulant Snit

I'm a selfish bastard.

No, that's not the big announcement mentioned yesterday. We all already knew this.

No, this is more personal. See, I'd like just once--just one single effing time!--for someone else's NMR tube to break, spilling their carefully crafted molecule all over the inside of the transportation bucket. I'd like, for a change, to go over and not find half an NMR tube awaiting me where its jagged, sharpened edges glint with the sad remains of a once proud synthetic intermediate.
I guess you can figure out how my afternoon went.

This isn't the first time such a tragedy has befallen yours truly. In those final days of grad school, when any student worth his snuff is working desperately to get those final few molecules characterized and the experimentals written, such a doom fell upon my shoulders. I had synthesized a particularly devious aldehyde (for those unenlightened in the art of organic functional groups, aldehydes tend to be very reactive and, therefore, very unstable) and carefully had purified it. I took a rather crude 8-scan proton NMR and saw that the product was beautiful, pristine, immaculate with an easily-discernible E to Z ratio (it was a cross-metathesis product).

"Beautiful!" thought I, as I laid my eyes upon the FT readout. "No one has reserved the machine for carbon-13 tonight! I'll come back and retake this tonight and get a carbon at the same time." A well-laid plan, if ever I saw one. Yet, I've heard, these often go awry. I ended the scan, stopped the spinner, and ejected the tube out through the top of the machine. I am always very careful with my samples, but, just this one time, my concentration lapsed for a mere moment and I bumped the bottom of the tube against the lip of the sample injector, jarring it from my hands, causing it to spin slowly away from the top of the 300 MHz Varian machine I had lovingly praised moments before, and saw it shatter into a million tiny shards laced with a thousand droplets of deuterated solvent and perfect product.

It was, of course, all of my material. This set me back two weeks, thanks to the need to synthesize the aldehyde under very careful, dry conditions (actually, it was a PCC oxidation, but the material often fell apart upon work-up and chromatography). My friend Clara was standing right there as I looked down upon my shattered hopes and, tears barely staunched in my eyes, I announced: "God hates me." The look of compassion and empathy in her eyes was palpable. Dejected, I swept up my mess, discarded it in the broken glass container, and marched the very lonely three flights of stairs up to my lab wherein I sat at my desk and sulked and pouted.
Then I went and ate a large dipped cone from Dairy Queen.

Abuse of Language

The other day, I was in lab talking about something, some reaction or such, and I said, "What's the worst that could happen? An explosion?" The labmate with whom I was speaking and I had a nice chuckle, and then he said "Well, I guess we could always crank the heat up and see what happens." To which I replied, "Don't blame me when it goes 'Poon!'" I then used very large, sweeping hand and arm gestures to pantomime the billowing clouds of fire and smoke as I wrapped up my sentence.

Then I realized what word I used to recreate the onomatopoeia of the explosion. My labmate and I had a good laugh over that, too.

I realize I'm going to probably offend my female readers here, but this little exchange got me to thinking. We have a perfectly lovely and utile language here in English, and yet we seem to spend most of our creativity on developing and inventing clever words to describe our sexual organs. Take, for instance, poon. Said in a deeper, almost airy way, it's a lovely way to describe the sound made during an explosion. However, I think we all know its "true" meaning--actually, the word "poon" is often used to reference a certain group of trees from the East Indies known for their solid, durable wood. Yep, that's right. You get hard wood from poon.

*taps microphone* Is this thing on?

It's not even taking another word and twisting it to some perverted means, like hooters. We all know what hooters are, thanks in large part to Al Bundy and that rather mediocre restaurant. I prefer to think the Al Bundy had more to do with it than the restaurant, but that's just me. We can make up any number of words to describe a body part, and instantly one knows what it means. Such as, if I were to say, "Wow! Look at those mugumbas!" you'd know instantly that I was ogling some girl's breasts.

Of course, this doesn't stop with just the female body. It works for the guys, too, lest we forget James Van der Beek's soliloquy from Varsity Blues in which he lists a very long stream of words, phrases, and descriptors for the penis. Or the wangdang. Or the John Thomas. I think I've made my point.

If nothing else, I've proven on this here little blog that I'm fairly proficient at throwing around words that some people consider offensive. So, it might seem like I'm a hypocrite, complaining that we're using our creativity to come up with new words for our naughty bits--especially when I use them every day. Maybe I am, maybe I'm not; that's for you to decide. However, in all the words used to describe genitalia, there is one used to describe female genitalia that I find completely and downright terrible, and thus I never use it.

Yeah, that one.

I'm So Tired...

I haven't been posting a lot lately. My kids went to visit their grandparents last week for spring break, and I've been doing a lot of work around the house trying to get it ready to put on the market so we can move. Exhaustion has been, well, an understatement, to be honest. There's still a lot to do. I have to finish hanging the baseboards in the bathroom downstairs. I have a few more screws to screw into the shutters on the second story. I have to pound some edgers down into the ground around one of the beds I made at the back of the house and I have to finish putting the edging in on the bed I made at the side of the house, plus I need to put down some more mulch and some more stones in various beds. This is not to mention all the mowing and edging I need to get done, too. I guess I just need to find the right tools for the jobs at hand.

On top of this, I'm starting up a new project at work. It's fun, but it's got some tougher chemistry involved, plus, I've got so much to read when it comes to papers and such. There's a whole bunch of biology to learn, there's biological tests and assays I have to familiarize myself with, and then there's just the new chemistry that has to be learned (I did a Baeyer-Villager the other day...and it was fucking sweet).

The thing that's tired me out the most, though, is the whole writing thing. It's not that I have a lack of topics swirling around in my mind; quite the opposite, to be honest. But, also, honestly, it's tough to find the time. I just put the kids down to bed and I still have to gather up the trash and take it out and straighten up the kitchen. By the time I'm done with that, it'll be well after nine, and already I need to start getting ready for tomorrow when I get to do it all over again.

The thing that I'm most tired of, though, is rejection. Yeah, I got two more emails this week telling me thanks but no thanks. Or whatever the form rejection is these days. It's not us, it's you. It's just not what we're looking for. Grow a larger copulation organ now. All of that crap. It's soul-crushing. I realize you have to keep trying, but I've been working on these things now for years. Too many years to even think about, because when I do, I just get depressed more. I've progressed very well on the whole Hundred Kings Saga thing, but now I'm getting to the point of wondering why should I even bother? I pour my heart and soul into carefully crafting a land and characters to populate the land and all the other subtle little nuances that breathe life into a set of words and make them a person and all I get is "Sorry, no."

I guess the big problem is that I'm tired of the form letter. You know, you could at least put my name in the title of the email. "Dear Author" just doesn't cut it. Blegh. Thanks for carefully considering my book/letter/synopsis. Next time, introduce yourself right before you kick me in the nuts, okay?

Maybe I'm slitting my own throat with this post, but I just don't care anymore. I just don't. I'm out. I'll probably keep working on the stories, but they'll be all mine. I'll be happy with the way they end and how they work out. But, I won't cry over the little details that I've worked in only to have some heartless assistant send me a form rejection letter. Screw that. I don't need that stress on top of it. That's right, I'm giving up. Even though we didn't give up when the Germans bombed Pearl Harbor, I'm giving up now.

So, this is the end. I'm getting out of the writing business, for a long while. That means things will slow down here even more. Don't worry, I'll still be puttering around your sites (I mean, I have to have something to do between reading ring-closing metathesis papers) and still providing my soulful wit in your comments sections. But, for the most part, I've ridden off into the sunset.


Thanks, all. It's been fun.

Sayonara.

I'll let Bender say the rest.

Not Quite Sleeping Beauty

This just probably proves that I'm a sadistic bastard (but some of you would have it no other way), but this story is too good to pass up. At least in my quaint little corner of twisted reality.

I was in the lab the other day, waiting for my column to finish running on the Companion. While standing there, I was staring out the windows and noticed a body sprawled across one of the benches of one of the picnic tables outback. I immediately assumed it was someone from one of the companies that has offices and labs on the front side of the building, and I also assumed that it was a certain Chinese guy that works there. Now, before you get upset with me and label me a bigot, I'll just point out that most of the guys who work there are Chinese, AND it's the only company that has no offices on the backside of the building. This guy, though, always throws me off because he looks like a Chinese version of my friend Ozzy. The very first time I saw him, I thought "Shouldn't you be playing catcher for the Dragons?" Ozzy plays semi-professional baseball in the Chicago area, in case you were confused by my thought pattern there.

Since I had nothing better to do than make sure my column didn't over pressurize, I kept an eye on the figure. Finally, after about fifteen minutes (I had changed to a new column at this point), he stirred, sitting up and confirming that it was, indeed, the False Oz. However, my delight at pinpointing the guy from an educated guess was amplified when he tried to stand and, evidently, did not realize that his legs were numb. CRASH! to the ground he crumbled, eliciting a tumult of giggles from my oh-so-mature throat. Pulling himself to his feet, he tried to walk again and BOOM! to the ground he fell. I'm chortling with delight at this point. Finally, he pulls himself up onto the bench and sits for another five minutes, bouncing his legs to work feeling back into them. Finally, he stands and, slowly, begins to walk with the shambling gait of a bog zombie or a newborn calf. He manages to make his way across the road to the building and from there, he disappears from my sight.

Having been thoroughly entertained for a good twenty to thirty minutes (give or take), I return my vigilent watch to the column. When it's done, I clean everything up and decide to make a restroom run (I've been drinking a lot of water of late...more on this later). As I complete said task, I wash up, leave the bathroom and make my usual jaunt through the lobby area where I see the False Oz just now getting up the steps and making his way over to his work.

Wow. Now, I'm not exactly a ball of fire on most days, but even I draw the line at napping on park benches during the day. No sir, I always take my naps on the toilet (after waltzing in around ten a.m., googling my own name for two hours, and then taking a donut break...unfortunately, I yelled this out while making love to my wife one night, so she's onto me).

Totally Mundane Update

A quick little follow up to the red cloud of death I generated last week.

I did the same reaction today, but made sure my stuff was good and clean before I added the nitrite. This time the solution just turned yellow and bubbled. I was paranoid and ran a vent line out into an Erlenmeyer full of DI water, just because I'm ubersafetynerd like that.

Hooray for me.

Rolling Red Clouds of Death

Yesterday, I had me some fun in ye olde lab. Some of the old school kind. And it involved a diazocompound.

I know what you're thinking must have happened if I mention diazo. No, no, rest assured that all flasks are still present and accounted for. There was no reason for two of my grad school professors to show up and chant "You'll blow your nuts off! You'll blow your nuts off!" (Two of my professors went to great lengths a couple of times to try and pound into our thick skulls the dangers inherently built into diazocompounds, like their tendency to go BAM!, and not with powdered sugar). This was an entirely different beast altogether.

All I wanted to do was to convert an amine into a hydroxy group, which I've done by this route maybe two dozen times now. So, yesterday, I took my amine up in glacial acetic acid (as per usual) and I stirred it vigorously under N2 (as per usual) and then I took my sodium nitrite up in water to make an approximately 2M solution (as per usual). When I added the first drop, everything changed color drastically. Usually, it goes from pale yellow to bright yellow as the diazo forms and is replaced by water. This time it turned dark brown/orange. Better yet, it started making a gas that was the same color.

Instantly recognizing it for the bank of death that it was, I acted. Fortunately, from my bigass hydrogenation days, I had a sparge line set up, and I jammed that into the flask and quickly affixed the outlet hose with a pipet which got set in an Erlenmeyer of water. I watched as the Orange Death slowly made its way through the tubes to the water where it harmlessly dissociated into nitric acid. Later, after (somewhat miraculously...it seems) my reaction went to completion, I was smart enough to flush the solution with nitrogen to chase out the rest of the gas before I continued on with the work up. Today, I isolated a beautiful white solid, which is amazing since everything was black and orange (screw you Warsaw Tigers!). The LC\MS even confirmed it was the right stuff.

I'm not sure why this time was different than all the rest. I guess my starting material wasn't as clean as usual (which is true) and that something in there caused the generation of the N2O4. Whatever, no one got hurt or dead (which is most important) and I have a gram of nice, clean material to carry on to further reaction.

Too bad I'm taking a couple of days off and won't get to do anything with it until next week (more on that later).

Welcome to the Fold, Antimony

Now, I'm not the kind of guy who goes out of my way to try some fancy, exotic transition-metal catalyst. However, there are some I will trumpet from the tops of the mountains (such as ytterbium (III) triflate, which I used at my old job to do just about everything). When I come across a method for making something that I can't get done under some other, simpler way, I will use the new and exotic method. Plus, it's cool when you can use something new. In the back of my mind, I've kept a running tab of all the spots on the periodic table where I've used an element. It's sadly nerdy, but I am a chemist, after all.

In light of my inability to do certain types of palladium-based coupling reactions, I've had to find a new route to developing the SAR around our superduperriffic compound that we've been making and testing. One way, instead of coupling the free amine sticking off a heterocycle with an aryl bromide, is to try displacing a chloride off the heterocycle SNAr-style with an aniline or an aliphatic amine. The problem is, how does one go from an amino group to a displacable aryl halide?

Simple: you diazotize the amine in an aqueous acid and then convert the hydroxy group to a chloride using the appropriate reagent. I was doing this in two steps using NaNO2 in HOAc followed by stirring in warm POCl3 for a couple of hours. This was working great...until someone else in my company decided to paint the inside of their hood bright-ass yellow by means of an angry flask of POCl3 (hence known as "Pockle-3"). My safety-conscious company has decided to start making sure such volatile reagents, such as Pockle-3, are in the hands of people who know how to handle them. This is not a bad thing; at my old company, the procedure was to cool the Pockle-3 in an ice bath and then chuck in whole chunks of ice while stirring to induce things to crash out and then pour off the Pockle-3/ice/water solution from HELL. Usually into a mixture of halogenated and non-halogenated solvents. My old company wasn't big on safety. Or chemistry.

I digress. Now, enter me, who is staring at the dubious task of trying to make multiple grams of material with the chloride in place (a fluoride would probably work better, but I REALLY don't want to work with DAST). This would mean several multi-milliliter reactions featuring Pockle-3. Not wanting to have to do a safety review on each of the reactions, I decided to find a way around this mess. As it turns out, you can treat the amine in question with t-butyl nitrite in DCM with a little bit of dichloroacetic acid around to diazotize the amine and then addition of antimony(III)chloride will substitute the diazocompound with a chlorine (this can also be done with bromines, as well, using the appropriate brominated compounds). Boom. There it is. One step. Sure, the process takes two days, but between diazotizing, purifying and then hitting the hydroxy with Pockle-3 also takes about two days. Unfortunately, my compound, as unyielding as the relentless pounding of the surf against the shore, only formed the chloride in ~20%. ~70% was the hydroxy with ~10% left over as unreacted starting material. So much for great strokes of genius.

So now I've decided to just put up with the safety committee and go before them, goggles in hand, to be educated as to the ways of dealing with Pockle-3. In the meantime, this was the first time I had ever used an antimony compound. I know that salts of antimony can be used to kill the worms that cause leishmaniasis (I actually asked a girl out in high school whose name was Laurie Leish); unfortunately, the antimony salts also kill the people infected with the disease.

However, this allowed me to fill in one more spot on my "I've used that!" periodic table. Behold:


Sure, some of them are cop-outs, such as I use carbon everyday and most of the time nitrogen is in a ring, or some such. I've never actually taken nitrogen and tried to get it to bond with a transition metal or something. However, I have used the nitrate to do the diazotization reaction. Likewise, I've only ever used cesium in cesium carbonate form (damned fine base, by the way), but it's still cesium. You'll note I highlighted technecium; I'm not sure what technecium can be used for, since it's radioactive and (mostly) man-made. However, I had it shot into me, as outline in the first part of The Ordeal that I wrote about months ago.

So, there you have it. One more box colored in. I'm half tempted to color in thorium, since I've nicknamed my rotovap "The Mighty Thor". I feel that rotovaps work better if you stroke their egos before using them.

Lab McGuyverism

When in a pinch, an average wood screw (I believe this was about a 2 and 1/2 inch, number 8) will substitute for a glass cutter. Two or three scores down the back of your TLC plate and a soft tap with the bottom of an acetone wash bottle will leave you with a nicely halved plate, so that you can throw away the results of the column you ran last week but keep the results of the reactions you ran in parallel on the same day.


Wood screws in organic chemistry: not just for illustrating chirality anymore.