jam∙at∙registration∙roller

 I’ve realized that the recent end of ski season marked the end of phase one of my graduate school career.  I can no longer take a month off to relax in the mountains and spend 15 of 20 days skiing.  I can’t let a month (let alone a week or even a day) go by without spitting out reactions, reading ASAPs, or working on mechanism problems.  That being said, I still have evenings and at least one day of the weekend to myself, without having to worry about studying for classes or memorizing 229 name reactions.  Backpacking season is basically here, climbing has already started, and fishing and biking adventures have yet to begin.  Pictures are going to start flowing onto the white space of this page as I suck up every bit of my free time in the Colorado wilderness.  In tribute to the passing ski season and in anticipation of my upcoming adventures, I am posting my favorite pictures from this winter, taken at Keystone, A-Basin, Breckenridge, and Steamboat Springs.  Enjoy!

 I joined an elite group on Sunday.  Granted, this group is relatively easy (although not painless) to join, and no one has successfully failed at gaining membership.  I don’t think an official name exists, but I’ll call the group The Society of Otherwise Healthy Chemists who followed Brandon to a Rock Slab and Hurt themselves whilst Trying to Climb It.  I sprained my ankle.  I guess my dues were cheap (considering Kenny needs a root canal).

 We started the day around Red Feather Lakes at a boulder with a cool mantling problem.  Jenni captured my pathetic attempt (although I later figured it out):

 Kenny worked on another part of the boulder:

…then moved on to the "Classic Warm-up Boulder" 

I sprained my ankle on the "warm-up" boulder.  I think this is post sprain, before I gave up:

 I became photographer as the rest tackled a new problem:

Conclusions from this trip: (1) don’t sprain ankle climbing, (c) learn to fall like Jenni, (2) ski poles make great crutches, and (b) I need a new camera (most of these were taken on Aaron’s dSLR).

 I’m a huge nerd.  I set up a program called LogMeIn on all of my computers today.  As long as they are on and connected to the internet, I can remotely control any one of them from anywhere.  Cool?  You’d better believe it.  Pictured below, I connected to my desktop from my laptop:

 Pretty nifty.  To prove to myself that it was working, I cranked up the volume until I could hear it upstairs.  Ok…more about LogMeIn.  I’m using the free version, which is limited to remote access only.  It does sync up the clipboard of both systems, which is a pretty slick feature.  It supports both Mac and PC.  Here, I show how I can control the Mac sitting 3 inches to my right from my PC:

 If you have money to blow, consider the Pro version, which clones the audio to the client computer, supports drag-and-drop of files between computers, remotely prints documents from the host computer to the client’s local computer, and a bunch of other crap that I probably wouldn’t use.  I choose to save my money, log in to my home computer remotely, and email myself files that I need.  Who needs drag-and-drop anyway?

 As proof of concept, I logged on to my Mac from my laptop, then to my desktop from my Mac from my laptop:

 I debated logging on to my laptop from the desktop, but I’m afraid of what might happen.  It’s too late for me to think too hard about it, but I don’t want to try to remotely control a computer from that same computer.  I bet Mike could make a spreadsheet to calculate the physics behind it.

 While these examples were a bit unnecessary, I did use LogMeIn legitimately 2 times today at work, and semi-legitimately once since I got home to avoid walking downstairs.  Thanks for telling me about this EA!

 Having climbed regularly at the gym for about a month now, I caught myself becoming content with the chalk encrusted artificial holds, fixed ropes, and the climate controlled environment.  I tackled a new beast today in the Poudre Canyon.  The Palace.  I would guess there are close to 50 sport climbing routes in this area, so even though the river crossing didn’t dissuade the masses, there was plenty of room to spread out.  The water was not surprisingly freezing, because, as Aaron pointed out, it was snow yesterday.

 We decided to "warm-up" on a route called #1, a short 5.9+.  I’m a little bummed that my first outdoor climb didn’t have a cooler name, but I suppose "#1" is appropriate.

Kenny climbing lower part of #1.

 Next we climbed Churchill Rejects, another 5.9+.  I stole this picture from Mountain Project. 

 Hiked a little farther and hit Escalera, a 5.8.  Yeah, it means ‘ladder’ in Spanish.  The rungs on that ladder were really freaking far apart.  It had a cool chimney at the end.  The only picture I have of this route is of Aaron on belay.

 I attempted Monstrosity (5.10b) and Ghost of Cedar Creek (5.11a)…next time.  It was an awesome day, as anyone that knows me well can gather from the lack of pictures.  Classes are over, summer is here, and I plan to spend as much of it outside as I can.  Since ski season ended, I haven’t done much outdoors except sitting on my porch.  The gym won’t feel the same now that I have reminded myself that there is fresher air than A/C. 

 Ah, students and their clever lab reports.  I took pictures while I graded today to document some of their fine work.  The first is an example of ambiguity:

 The, "throw in big words that we haven’t used yet in our conclusion in this sentence fragment" report:

 "I don’t want to look up any real safety info so we’ll make some up":

 "Hey, let’s blame the TA for our shitty yield!":

 One of my personal favorites, the concerted reaction mechanism:

 This conclusion is a little too concise:

 And this one is a little too long (this comment refers back to a statement made 3 pages earlier in the conclusion):

 ’A’ for effort doesn’t always apply.  I think "good try" is more appropriate:

 The complete NMR interpretation:

 The 40 page lab report: 

 I am now officially done grading lab reports for the semester.  The above examples are from one set of reports…as you can imagine, I’m glad to be done. 

 I’m lazy.  Maybe efficient is a better word.  Especially when working on the computer, I despise repetitive actions.  I will go out of my way to write a macro, create a shortcut, or use a hot key to avoid one extra keystroke.  Seeing as how creating schemes in ChemDraw is by nature a repetitive process, I feel that I have developed optimal drawing technique for minimizing keystrokes.  Use the following suggestions and cut 2 days off of your graduate school career.  Or take an extra coffee break per week.  I really don’t care how you use the extra time, but my 15 steps to ChemDraw success will make you happier, lose weight, and feel great about yourself.

 I’ll start out simple.  Draw a benzene ring.  Double click it.  Type ‘ctrl+c’ (or ‘apple+c’ for the mac toting readers).  Type ‘ctrl+v’.  Now you have 2 benzene rings!  Copy and paste will be your best friend when using ChemDraw.  You can highlight a structure to select it, but my experience has found double clicking an atom in the structure to be more reliable at selecting every atom.

 Simple.  Just wait.  It gets better.  Let’s turn benzene into pyridine.  How would you normally do that?  Probably by selecting the ‘Text’ tool, clicking one of the carbons on benzene, typing the letter N, and clicking off the molecule.  I can reduce that process to one step.  With the ‘Benzene’ tool still active, hover over one of the carbon atoms and type ‘n’.  Now you have pyridine.

 Now, how would you normally change that to piperidine?  Redraw the whole structure?  It is probably just as much work, but I’ll use this as an example for changing bond order.  Hover your mouse over one of the double bonds and type ‘1′.  Whoa.  It’s a single bond now.  Do that 2 more times and you’ve made piperidine!  You can change any bond to single, double, or triple in the same manner by typing 1, 2, or 3, respectively.

 Now, piperidine to 2-tert-butylpiperidine.  Select the ’solid bond’ tool, click the 2 position, then hover over the end of the new bond.  Type ‘8′ to "sprout" the 3 bonds of the t-butyl group.

 Now, define the stereochemistry of our new stereocenter.  To make this bond hashed, I used to delete the bond, pick the hashed bond tool, and draw in the new bond.  Turns out you can simply hover over the bond and type ‘h’ to make (S)-2-tert-butylpiperidine.

 Now, to demonstrate the next trick, I converted this to the chair form.  Notice the bond to the axial hydrogen in the structure below.  It should be solid, and the back C-C bond broken to show that it is behind the C-H bond.  To bring the C-H bond to the front, hover over the bond and type ‘f’.

 Charges can be added in the same way.  Hover over an atom and type ‘+’ or ‘-’.  That’s it for my cool hotkey tricks.  The next few suggestions are more commonly known, I think.  To align your structures so they are centered vertically with respect to the reaction arrow, select the products, reactants, and arrow, then right click > align > T/B centers. 

 For those of you studying name reactions, that is an Aza-Claisen Rearrangement.  I am usually very picky about alignment with my schemes, and I’ve found that an even quicker way of lining up reaction arrows and structures is to make use of the drawing grid.  It can be turned on or off using ‘ctrl+h’.  Arrows in my schemes are always the same length…this is a personal preference that most people don’t share with me.

 I also wanted to point out the character map toolbar in ChemDraw.  Any symbol not on the keyboard is on that toolbar.  To pull it up, click view > ‘Show Character Map Window’.

 The ‘clean-up structures’ tool (ctrl+shift+k) is good at fixing bond lengths and angles.  ChemDraw can also predict carbon and proton NMR spectra for molecules (Structure > Predict NMR Shifts).  Lastly, when typing in a formula, press ctrl+f to get ChemDraw to recognize it as a formula and sub-superscript appropriate numbers and charges.  That’s it for my tricks.  If you know more, please, enlighten me.

 All of the structures above were drawn with my favorite object settings (very similar to the ACS Document 1996 preset).

 Happy ChemDrawing.  I expect $5 for every new trick I taught you. 

 As an undergrad, I would go to Vermont St. BBQ every Thursday night for the 25 cent wing special (it went up to 35 cents the last month I was in Lawrence). 

 Link and Phil argued that you could eat as many wings as you could afford ($3-$5 was a lot of money back when I was an undergrad), as long as you "surprised the stomach."  Our tactic was to sneak up on the stomach, catch it off guard, and stuff as many wings down it as possible before it figured out what was going on.  It always seemed like it caught on to our motives after about 20 minutes of binge eating.  I decided to see if there was any (peer-reviewed) scientific basis to this, and after some digging think we may have been on to something…

 Eating behavior is a complicated mixture of biological and environmental variables.  There are three major types of variables; those that cause us to (1) start eating, (2) keep eating, and (3) stop eating.[1]  For the purpose of this discussion, I’ll focus on the biological signals that are responsible for our satiety, the feeling of fullness that makes us stop eating. 

 Levels of the hormone cholecystokinin (CCK) increase while eating.  Binding of CCK to receptors on the central nervous system triggers physiological responses, including an increase in gut motor activity and pancreatic enzyme secretion.  More importantly for my argument, CCK seems to trigger a satiety response from the brain.  In the figure below, the concentration of CCK is plotted against time.  The subjects were fed various meals (the different lines) steadily over 10 minutes before their CCK levels were monitored. [2]

 Hey, guess what?  CCK levels initially peak around 20 minutes!  (OK, that’s the first data point, but who gives a shit?  It’s still a peak.)  The authors of this paper also present another figure in which the change in satiety response of the subject (a subjective rating based on a scale of -3 to 3, -3 being extremely hungry and 3 painfully full) is plotted against time: [2]

 Again, the peak is at 20 minutes.  I think the best comparison to our consumption of wings is the bacon and egg meal, represented by the open triangle in both figures.  Now, I wouldn’t be much of a scientist if I took this one study as proof of the surprise the stomach tactic.   Devlin et al. published a paper on CCK response in patients with bulimia nervosa.  They also observed that CCK levels peak 20 minutes after the start of the 400 gram meal (at least for the non-bulimia control group). [3]

 CCK tells our brains that we are full and should stop eating.  Serum CCK concentration peaks around 20 minutes after the start of a meal, so eating quickly should allow one to consume more food.  There.  I manipulated the data to my end and proved that Surprising the Stomach is a valid eating tactic when trying to consume the maximum amount of wings possible.  Eat as many as you can in 20 minutes and don’t let the stomach know they are coming.

 If any of you are more knowledgeable on this subject, either from the scientific or practical sense, please chime in with your opinions.  I’m off to once again prove my theory. 

[1] Schwartz, G.J. Obesity Research 2004, 12, 102-106.
[2] Holt, S.; Brand, J.; Soveny, C.; Hansky, J. Appetite 1992, 18, 129-141.
[3] Devlin, M.J.; Walsh, R.T.; Guss, J.L.; Kissileff, H.R.; Liddle, R.A.; Petkova, E. Am. J. Clin. Nutr.  1997, 65, 114-120.