It's Ash Wednesday, Y'all!

Typically, on a day like today, I'd break down the history behind the holiday and/or saint's day, interspersed with tiny little nuggets of extraneous information that would make the post slightly more amusing.

Today, I'm not going to do that. Perhaps it's the solemnity of the holiday, perhaps it's just that I'm ass-tired, or perhaps it's because I've been blowing my creative wad on the comments in your blogs. You have to admit, I've been pretty fucking clever this week, making up for last week's dearth of funny and/or pithy comments.

Anyway, I'm going to give up a couple of happy little stories today in honor of Ash Wednesday that are appropriate, given the holiday. Buckle up, bitches, we're going for a ride on the way back machine. Hold me, Mr. Peabody!

First off, we anachronistically arrive in spring of 1998. I'm in the throes of Catholic Conversion, and so I attend the Ash Wednesday mass. My friend Jeff was an alter attendant...or whatever they call the not quite priests doing the priestly duties. Jeff is now an ordained priest of the Society of the Precious Blood order. You should bear that in mind whilst I go through the tale.

There I am, standing in line, heading up toward the alter where I will get the ashes decorated on my head to loudly announce to the world that "I am Catholic, and I went to Mass. Suck it, pagans!" Sure, I wasn't a full member of the church, but you didn't have to be Catholic to get the ashes. You can just come in off the street and get the mark. Pretty keen, eh? The Catholic Church, much like the Catholic Girls, are all inclusive and will let anyone in.

So, I approach my friend Jeff and lean down (I'm taller than he, but about six or eight inches) and I see him working his thumb in the ash tray furiously, like he's trying to smash a bug beneath his thumb and grind its guts to Hell. I catch a fleeting glimpse of the ashed thumb as he raises it toward my head. It's black. Not just dark, sooty gray as one would expect. No, this was a black so pure, so powerful, that light itself was bent around it as it got sucked in by the absorbative properties of the color. "Great," I think, "he's going to put that on like graffiti." I braced myself for impact.

It wasn't just that he was going for darkness; he was going for maximal coverage, as well. Starting at my hairline, he dragged his thumb down my forehead to the bridge of my nose. He then reupped the ashes and started at the hairline of one temple and dragged his thumb across my brow to the hairline of the other temple. At that moment, there were about thirty, maybe fifty (at most) people still behind me in line, plus, I was in a church, so I had to stifle my urge to scream out "Jesus fuck, Jeff, would you like me just to roll in it like a dust bath?" I also, since he had made his intentions well and clear that he was going to enroll in the seminary that fall, couldn't slug him the gut. I mean, the man was going to be a priest and all.

So, I closed my eyes, offered a heavy sigh, and whispered "Amen", then departed to go back to my seat. One of my friends sat down beside me after she got her ashes, looked at my forehead, and burst into fits of giggles that wouldn't subside for a good forty five minutes afterward. I know this, because we went to lunch immediately after. Along the route to the cafe, everyone whom I passed suffered a similar fate. Those with more tact at least were able to twist their mouths up and stifle their laughter until after I passed, and some of them were able to utter a sympathetic "nice".

Let's hop back in the time machine and this time set course for spring of 2000. I'll set the stage for you here: I was young(er), I lived alone in my own apartment, I was currently enrolled in grad school where I was surrounded--pretty much daily--by hordes of nubile, college-aged girls who, when spring arrived, liked wearing very little. I was also recently single and had no steady girlfriend at the time. Got all that? Good, let's proceed.

Back then, I reveled in my Catholicism, and so I'd try to give up something hard. One year I gave up alcohol, another I gave up desserts and snacks. Pretty standard fare. Well, in spring of 2000, for some reason, I got it in my mind that I would give up masturbation. I felt I was doing it too much and too often, and so I decided to just up and quit. I'd be less lusty, my carpal tunnel would clear up, and my clothes would stop reeking of musk.

Now, my friends that I hung out with most of the time were all female. There were three of them with whom I entered the same research lab and to say that they were a little prudish would be an understatement. If I recall correctly, none of them were Catholic (which might explain it), but they simply did not discuss anything that even remotely had to do with sex. Or bodily functions. Or, well, pretty much anything that I would classify as humor. Yeah, I don't get it, either.

So, when Lent rolled around, one of them asked me what I was giving up. Knowing that they wouldn't exactly want to know about my extracurricular activities when at home, or driving back to my apartment, or if I was bored in the computer lab, or even walking past Touchdown Jesus, I blurted out "I'm giving up candy." Seemed logical enough, and it was one of those things that was a fairly common sacrifice.

On Ash Wednesday of that year, I went and got my lunch, and decided that I really wanted a milky way (God's gift to candy, with its perfect proportions of caramel, chocolate and nougat), so I went to the little college store there and bought one. No big deal. I slap it down on my tray for eating after I finished my salad or whatever meatless meal I was enjoying, and one of the girls points to the candy bar and says:

"I thought you were giving candy up for Lent!"

In a mad panic, my eyes go shifty, I break out in a sweat, my face flushes and my heart races. Finally, I managed to calm myself enough to offer a small nod and said, "Yes. Yes, I am." I tossed the snack in my backpack and carried it around with me for the remainder of the day, craving its gooey goodness. When I got home that evening, I pounded down the Milky Way as if my life depended upon it. Then I realized that there's no eating between meals on Ash Wednesday, so that ended up being my dinner. Meatlessness has never tasted so sweet.

I met my wife a couple of weeks after that. When I introduced myself and shook her hand, I couldn't help but notice the twin midget wrestlers fighting for domination in her shirt, and, since the carpal tunnel had been clearing up, my grip was nice and firm, in that sort of "Oh God, I'm staring at a hot redhead's breasts and I can't do a thing about it" way. Two years later, after we were married and when the movie "40 Days and 40 Nights" came out, I confided in her what I had given up that year. All she could say was "Wow."

In case you were wondering, this is my 400th post. I thought about doing something deep and reflective, but instead, I decided to offer up the tales of how my forehead was violated by the thumb of a priest and how I managed to stave off autoerotic pleasures for six and a half weeks. What will the next 100 posts bring? Probably more masturbation stories. Huzzah!

Methinks the Blogosphere is Trying to Tell Me Something

I was just scratching that foot-fetish itch over at SouthernBelle's blog when I wrong something mildly amusing in the comments section about time travel and Australia and Dirty Sanchez. When I went to punch in the secret code on the word verification so I could collect my prize, this is what I saw:

Hmmm...I think that's a thinly veiled message. I think her blog...or maybe the internet as a whole...or maybe just my computer...seems to think that I'm a messed up fatso. And you know what? They're probably right.

Well, time to go polish off a package of weiners with a redi-whip chaser, and then hide under the dining room table in an attempt to keep MLB from reading my thoughts and studying my purchasing habits. And fantasize about Scarlett Johansson a bucket of green jelly and a goat.

Can I Go Home Yet?

Today is the first day at work under these new "daylight savings time" rules, and things have not gone as swimmingly as I might have liked. I'm always reminded of how much I dislike this whole daylight savings time thing when it rolls around, mostly because half the time I'm frustrated and confused by what the clock is telling me. Oh, sure, there's the inconvenience of setting the clocks back, or forward, or ahead by 42 minutes if you just wanna fuck with someone, but today is that day that I'm really reminded of just how inconvenient this whole thing is.

I don't know if I've ever mentioned this to any of you, but I grew up in the great state of Indiana, where we didn't have such things as daylight savings time or hobbies other than shooting and plowing. When I moved to North Carolina in the fall of 2002, I got my first taste of this crazy semi-annual event and it was then that I realized it left a sour, terrible taste in my mouth.

See, currently, it's 4:32 pm, but my finely tuned internal clock is telling me that it's 5:32 pm, and that means food and SpongeBob time. My brain is telling that precision instrument inside my body that, no, it's set up two more Suzuki reactions and update your notebook time. Well, perhaps my brain isn't saying this, but the clock on the wall, my computer and phone are saying this. More importantly, the clock on the wall, the computer and the phone are telling my boss that it's set up two more Suzuki reactions and update the notebook time. This causes me to sigh wistfully and wonder just what that plucky little poriferan would be up to now, had the world that suddenly jolted on its axis and stopped time momentarily, thus causing the world's clocks to lapse by an hour.

This happens at several times during the day for the first few painful penetrations days of daylight savings time, but it always seems to be exacerbated by the first day at work after we've changed the clocks. I get hungry during the midmorning hours, I don't get sleepy until the hour grows to an obscene lateness that all but ensures that the following day will be met with listlessness and fatigue, and I wake up an hour early, wondering why the hell I can't get back to sleep, despite the fact that it's pitch dark outside and no one is screaming that a passing aircraft has terrified them from their otherwise peaceful slumber.

I guess the only silver lining in this whole thing is that President Bush--rather than doing the intelligent thing and abolishing this madcapped, crazy scenario designed to save candles--shortened the duration of "standard time." It means that, in five months, we'll be switching back to "daylight time," and that finely tuned, precision crafted hourglass in my head can get back to getting hungry at noon, rather than 1pm. Or, wait, if I'm eating at noon, now, does that make it 11 am, or when we switch it up, will 11 am be 1 pm?

Oh, fuck it all, I'm going to get a drink and watch cartoons.

The Follow Up

I know you were all wondering how the...ahem...celebration of our eighth anniversary went last night. However, a gentleman never tells.

I, fortunately for you, am not a gentleman. In fact, I'm all about the gory details, right down the bodily fluids. Strap yourselves in.

So, we planned for a romantic dinner last night. We were going to go get some steak or maybe go to Ted's Montana Grille, because goddammit, buffalo is good meat. However, I ended up swinging by a bar and picking up some pizza. I came home to find my daughter in full-on meltdown drama queen mode because she couldn't find her colored pencils. My son met me at the door, snot running down his face, his cheeks pinked with fever. My wife had the glazed-over look of someone who had just seen a particularly gruesome car wreck...or had just spent the last few hours fighting over the location of a bag of colored pencils, all the while wiping snot from a feverish four-year-old.

We exchanged gifts. This is where it shows that we know each other after eight years of marriage: I got her a gift certificate for coffee and for shoes; she got me a book, a coffee grinder and a gift certificate for video games. We dined upon our pizza...after another fifteen minutes of full-on drama queen meltdown over the now found bag of colored pencils. After dinner, we watched Jeopardy and then it was bath time. My son took his and got tucked into bed, my daughter took her shower, and got tucked into bed. My wife and I hung out in our room for a little bit, she working on a writing project of her own, me flipping back and forth between the Monday Night Football game and this extreme marksmen show on the History Channel.

Finally, at ten o'clock or shortly thereafter, we settled down into bed and, just as I was turning off the light, we heard a blood-curdling scream. Into the room staggered the four year old, delirious with fever, telling of how badly he wanted his medicine. I hauled him into bed, my wife dosed him the appropriate medications, I slathered him down with a little bit of Vick's vaporub, and we settled down once more, four year old firmly (and wiggly) between us. Turning out the light once more, we wished one another a happy anniversary and settled in to sleep. About thirty minutes after turning the light out, the boy decided he wanted to go back to his bed. After tucking him in and telling him it was okay that he dumped out part of his medicine all over my side of the bed (most of it was on his shirt and his bear), I slipped back under the covers in my bed, ready to get down to business.

And by business, I mean laying my head down on a pillow that smelled faintly of spilled grape-flavored ibuprofen solution and falling soundly asleep, which is where my wife already was.

Ah, Parenthood.

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.

Deuces Wild!

I'm screwed up. Why, you ask? Well, it's 10:55 pm right now, but my happy little body is telling me that it's 9:55. It's all because of this damned "daylight savings time". I blame the difficulty to adjust on spending 26 years in Indiana (though for four of them, I lived in Rensselaer, which did follow daylight savings). If nothing else, I'm not only slow to pick up on concepts, but I'm slow to adjust to these sudden shifts in time that come twice a year.

And here's another thing. We're on daylight time now, or (for North Carolina), Eastern Daylight Time (EDT). We are on EDT from the first full weekend in March to the last full weekend in October, which is 8 months. That means we're on Eastern "Standard" Time (EST), for four months a year. How is this standard?

Another problem, I want to curse Benjamin Franklin for inventing this accursed way of conserving our candles. Despite what I was taught as a lad, this is not true. Franklin didn't invent it. Instead, he suggested that Frenchmen are lazy, offering "Early to bed, early to rise, blah blah blah" and then suggested firing cannons early in the day to roust the Frenchies from leurs lits earlier in le matin to get leurs culs paresseux up and working (lot of /l/s in this langue bete). This was met with much resistance (clearly, if Franklin fired cannon, then the Parisians would have risen from bed with arms fully raised over their heads)--and while the French thought the funny little bumpkin from Philadelphia was adorable with his bald head, sentient gout and pudgy paunch, they continued the practice of sleeping late. Then one day they woke up and everyone was speaking German.

No, the true culprit is one William Willet, an English builder. Willet was apparently a morning person, and took it upon himself, once he realized that people like sleeping, to ruin this habit because so many Londoners were missing the best part of the day (in his humble and self-righteous opinion). Here's the other problem with this asshat: he loved golf. In fact, he loved golf so much, that he was often upset when an afternoon session ran long and he had to cut back on the golfing because of darkness. Apparently, Willet had never heard of getting piss drunk at the clubhouse. Apparently, Willet also never heard of going to a burlesque house. Apparently, Willet was just an all around prick.


Have I not convinced you of the errors and evils of daylight savings time yet? Well, how about this last fact: the first people to use DST? The Germans, in 1916, during a little thing we like to call World War I. They also forced that shit on all their occupied territories and they shoved it down their allies' throats. Apparently, England and France decided to get up early (and you thought I was joking about everyone speaking German) to avoid waking up to the heady aromas of chlorine and mustard gas. Ah, trench warfare, your elegance is so misunderstood and understated.

And while you're springing forward, think on this: gasoline consumption in Indiana jumped by three percent (from 1% to 4% during the "saved" hours) after it adopted DST a couple of years ago. Wait. I thought all this nonsense bullshit was to help us alleviate our need of foreign oil. Seems as though someone forgot to carry the 1 while doing those complex calculations.

The only good thing I can see is that traffic fatalities are reduced when there is more light for the evening commute. This is a good thing. However(!), now I have to deal--once more!--with that accursed huge, red orb that sits exactly on top of the road as it rises slowly over the eastern horizon while I'm driving my daughter to school in the mornings. Its blazing light is enough to sear the very orbs from my sockets, bleaching the world in a bath of yellow and white light, sucking all other colors away as it crests above the eastern edge of the world. I can't see a thing beyond about three inches past my windshield. Yes, that's safe.

This might be my hot button issue for the election year: whoever says they'll abolish this fascist, vile, contemptible, golf-laden practice gets my vote. Unless it's Hillary.

P.S. This is my 222nd post. Hence the deucey goodness in the title.

No Excuses

I went on a rant against how awful Minnesota is/was when my beloved Hoosiers went up there and tried their best to crap the bed and lose. If it wasn't for Spencer Tollackson's piss-poor [1] showing at the free throw line, Indiana most likely would have lost that game. I ranted and raved about the unfairness of the refs and making Gordon sit and everything else.

Not today, my friends. Nope, the editors of "A Crown of Thistles"[2] demand some form of objectivity, and by that I mean if you suck, I need to call you on it.

Indiana, you suck.

At times, you can be brilliant. DJ White is a workhorse underneath the basket. Sure, Wisconsin's big men (and by big, I mean glacier big) were flopping whenever you'd make a move toward the basket, but you need to be sure to keep your head in the game. You're the only star on the team right now because Gordon hurt his wrist. Ohio State fans, I know your misery with the whole Greg Oden saga: you have a superstar from Indianapolis on your roster who is probably going to be there for only one year and he's playing with a hurt wrist. Not much fun. I feel you.

Still, someone needs to step up. DJ White can't do it alone, and DeAndre Thomas (all 290 pounds of him) is going to get called because he's big and, no matter what, the slightest brush with him is going to look like a foul. At the same time, someone, anyone! needs to figure out how to box out. Wisconsin's big players (and by big, I mean corn-fed and strong enough to bench-press tractors) owned the glass on both the offensive and defensive end.

And now for some personalized constructive criticisms:

Lance Stemler: stop heaving the ball at the basket and then running in trying to poke or slap the ball away. In fact, your sole mission should be to get the ball to Eric Gordon or Jamarcus Ellis or Jordan Crawford to shoot. It doesn't matter who you throw the ball to, as long as the shooter's name isn't "Lance Stemler".

Coach Samson: Lock Eric Gordon in a cage and poke him with sticks while playing Yanni. The only aspect of his game you can improve is his mental toughness. Sometimes he gets that hang dog look when the three isn't falling or the refs are calling it tight or his left hand is about to fall off his arm.

Luke Harangody: You're a stud. You're glacier big and corn-fed and can benchpress twenty tractors. Damn you (but bless you) for going to Notre Dame.

Steve Lavin: I like you. Just stop with the phrase "one and done". Be creative. "Another empty possession." "That's just as good as a turn over." "Lack of presence on the offensive glass." "What a fucking piss poor shot. Pull your head out of your ass!" "Indiana's playing on the offensive end like a sorority chick at a bar: one shot, and it's all over." Any of these will suffice.

Erin Andrews: Stacy Dales was giving Brad Nessler all sorts of grief during the UNC beatdown of Couldn't Cut it at ND U [3]. Maybe start giving Musberger a hard time, especially when he talks about wanting to take you to the Playboy Mansion. It could get him out of the booth sooner and then you can move in.

NC State: No one can piss away a 9-point lead and lose by 20 like you guys. Better keep hanging your hat on that bass fishing national championship from a few years ago.

I shut the game off at halftime last night because I was so disgusted. I turned it on again when there was two minutes to go, saw Indiana down by ten, and then went to bed. There used to be a time when Wisconsin was the bottom of the league. Indiana won 32 straight against the Badgers. I wish we could go back to those days, mostly because that's back when Indiana was consistently pretty good. I'm not saying Wisconsin is a bad team, but they're also not a great team. I think Indiana's steady diet of cupcakes during the early season is beginning to surface. Sure, beating Kentucky by a lot was nice, but that was at home. The win at Southern Illinois was also nice, but the Salukis need to really step up in the Missouri-Valley in order for that game to look impressive. And winning by a few over Georgia Tech is another glaring issue, although there's a chance that Georgia Tech will overcome the defections to the NBA from last year and end up third [4] in the ACC. Still, your rpi is somewhere around .500, and for a team ranked as highly as you are with a good inside-outside game like you have, you should be ashamed.

Ugh. Anyway. The sooner I can wash the bad taste of this out of my mouth, the better. Plus, I need to go home and reteach my daughter how to dribble. If nothing else, I at least want her to look better than Lance Stemler out there on the court.

[1] And by "piss-poor" I mean "0-for-7"
[2] me
[3] aka Boston College
[4] which isn't saying much, as it's pretty much "everyone after Duke and Carolina".

Right...the Big One Goes on Top

And no, I'm not talking about my sex life.

Today, I was trying to find the yield of a reaction I did yesterday. The product had dried overnight, so I was writing the numbers out on my in-lab notebook (read: my hood sash). I went through the calculations and discovered that I had made -0.9876 g. Imagine my delight at discovering that I had the power of a deity coursing through my synthetic hands. After all, only a god can destroy matter and make the sum total of the universe post-Big Bang come out with the negative sign.

That's when I actually looked at what I had written and discovered that I had made a slight error in my calculations. Reverting back to first grade (you know, when they teach you such shit like subtraction and addition), it occured to me that I was subtracting the weight of the flask and the material from the tare weight. Fortunately, it was early enough that I could hide my mistake from my co-workers and not suffer through their disdain. Of course, now I'm publishing this on-line for the whole world to read, collectively raise their fingers at the screen, and chant "Ha ha!" in unison. I'm a fucking idiot.

However, I'm an elated idiot, because when I finally put the big one on top (snicker), it turned out that I had pretty much a quantitative yield. This caused me to do a little, grotesque version of a dance. You see, for the past few weeks, I've been working on large scale chemistry that has frustrated the hell out of me because I'm not used to things crashing out of solution at the most inopportune times. Yet, despite these frustrations, I learned a lot about how to handle myself in these situations in the future so that if when I have to do this again, I'll be golden.

Now, to focus on that whole subtraction thing...

Wow, Do We Suck

I read something depressing in the hometown newspaper the other day.

My high school (Huntington North) beat local rival high school Homestead in football.

How is that depressing, you ask? It was the first time they had beaten Homestead since 1988.

For reference, I didn't even start high school until 1990. For further reference, none of the kids who play for my high school team were even born the last time HNHS defeated HHS on the gridiron.

Wow.

The kids were, of course, jubilant. I don't know if they actually realize that nearly a score had passed since there were similar jubilant kids on the field after playing Homestead. And you know what the really pathetic thing is? Homestead's not even the best high school in the area when it comes to football! I mean, sure, they're good, but they're not Snider or Bishop Luers or Bishop Dwenger. Couple that with the fact that Huntington North is one of the biggest schools in the area, and, well, you've got yourself a one-way ticket to Patheticstown.

19 freaking years. I hadn't realized. Christ, Indiana was preparing to defend a national title in basketball the last time the Vikings emerged victorious over the Spartans. The thing is, I don't even remember the last time Huntington North beat Homestead. Back then, all I cared about was basketball and Aleisha Crago's ass (and not necessarily in that order...). Wow. Compound this information with the fact that my cousin Scott went to Homestead and Homestead was in our sectional (used to be regional before realignment), so you can see that football expectations back at the old alma mater were never too high.

Nineteen freaking years. Incidentally, 19 years ago in August, the first night game was played at Wrigley Field. I watched both games (the first game on August 8th, was rained out and it was against the Phillies, I think) on tv. I had plenty of free time because, well, no one really cared about football in my home town and there was plenty of other things to watch.

Like Aleisha Crago's ass.

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.

Ah, Typical

So, last night, we had a couple of piss cutter rainstorms roll through. The first was a "strong, but not severe" thunderstorm, the last was, apparently, a severe thunderstorm, as according to the National Weather Service. I was rushing about trying to get the trash gathered up when I heard the heavens open up and inundate the north Durham area with canids and felids of various sorts.

As I was typing merrily along on Chapter 31 (it's not that I'm done, but I really began to see how I wanted to end the story as I sat down with a list of characters and decided their fates), the donder and blitzen were getting pretty intense, so I decided (after checking on the children to see if they were frightened half to death) that I would pack up and save my stuff. Instead of typing further, I decided to play Civilization III until the storms blew through, at which point I would suspend my game, gather the trash, and try to get one, maybe two more pages written.

Along about 11:30 or so, the storms finally passed and the rain died down. Now, rather than save my game, I decided to leave my industrious little workers building roads and other pieces of infrastructure that would help my empire's monetary wealth accumulate to the point where I could negotiate another cheap technology steal from the Egyptians. I was having a really good game playing as the Greeks, so I went about my business, carrying all the trash to the curb. As I was downstairs setting up my coffee pot for this morning's brewings, the power flickered enough that the answering machine in the living room erased and needed resetting. No big deal, I thought, as most of the clocks were alright. All of the alarms would still be set.

However, I came back upstairs to find the computer screen black. Again, no problem I thought. At this point, it was about ten till midnight, so I just turned the monitor off and headed off to fantasize about lost opportunities with Olivia Martin bed. My wife came home at the typical time (maybe a little earlier) and went to do the online bill pay on the computer.

One problem: the computer won't come on. The surge protector was fine, the monitor worked fine, but the computer was off. Our phone and cable were out, so I thought maybe that had something to do with it. The phone was on this morning, but still no computer.

So, here I am, stuck in the world with no computer, three nearly completed novels sitting on my hard drive (not to mention one kickass game of Civilization III featuring the Greeks) and all of the other files that go with them (lineages, images of coats of arms, house names, word counts). I'm a bit frustrated. However, this might offer an opportunity to get a newer, faster model. Who knows? The only problem is, I still have no idea how to get the old stuff off the hard drive if the computer itself won't come on.