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Jan
12:24 AM
0
A: Why is (1E,3Z,5E,7E,9Z,11E)-cyclotetradeca-1,3,5,7,9,11-hexaen-13-yne not antiaromatic?

JanThe textbook answer to this is that the triple bond consists of two orthogonal π systems whose interaction with each other is symmetry-forbidden. So as the attached figure shows, the two p-orbitals marked in red cannot participate in the aromatic system if the molecule’s structure is as drawn; th...

I love how a ‘simple’ question always attracts a complex answer.
 
@Jan At least, the question has got a complex name. ;-)
 
Jan
@Loong Oh yes, and I thank you very much for it, because I could easily copy the complex name from the title (and then add <i> and </i> where required) =D
 
Oh, I see you used <i>. I use the normal markup and add unicode U+2060 to separate expressions that do not want to work with markup.
 
Jan
I hate to admit this, but I don’t know how to enter cool unicode special characters with my keyboard (under xubuntu) without resorting to charmap =C
 
Maybe your result is even better since the output doesn't contain my invisible unicode characters.
 
12:39 AM
@Jan gosh, the first two times I read the question, I didn't realise Prof. Dimm didn't exist.
 
Jan
What, he doesn’t? D= I was hoping if that guy can make it, so can I .__.
 
Didn't we have another question that was "answered" by Sondheimer?
Ah, yes, the one about the Sondheimer annulene: chemistry.stackexchange.com/q/57678/7951
 
Jan
Looks it o.o But that’s a harsh way to put it, innit? ;)
They’re special ;)
 
:D
 
Well, we were all dumb once...
(Or still are hahah)
 
Jan
Considering most of the choices I made in the last six months: Yes, I’m very dumb.
 
1:21 AM
@Jan At least we're dumb in smart way :D
 
Jan
Or maybe we just think that, and actually we’re smart in a dumb way …? =O
 
xD
 
Who of you is Dunning, and who is Kruger? ;-)
 
@Loong Nah we're not talking about Dunning–Kruger effect, but tangentiality of wisdom and intelligence :D
 
Jan
I need to look up Dunning-Kruger; who wants to explain it so I can continue surfing SE?
 
1:34 AM
The Dunning–Kruger effect is a cognitive bias in which low-ability individuals suffer from illusory superiority, mistakenly assessing their ability as much higher than it really is. Dunning and Kruger attributed this bias to a metacognitive incapacity, on the part of those with low ability, to recognize their ineptitude and evaluate their competence accurately. Their research also suggests corollaries: high-ability individuals may underestimate their relative competence and may erroneously assume that tasks which are easy for them are also easy for others. Dunning and Kruger have postulated that...
 
Jan
A good thing that the basic explanation is typically within the onebox so I don’t even have to open the page =D
 
 
1 hour later…
user228700
2:50 AM
Yello everyone :-)
 
user228700
Does anybody know a better answer to this question:
 
Jan
!!wiki/Yello ?
 
Yello is a Swiss electronic band consisting of Dieter Meier and Boris Blank. The band is known for their 1985 single "Oh Yeah" which featured in the films Ferris Bueller's Day Off, The Secret of My Success, American Pie Presents: The Book of Love, K-9, and as the theme song for the character Duffman on The Simpsons. Their single "The Race" peaked at number 7 on the UK Singles Chart, and was also featured in the film Nuns on the Run. == Band history == The band was formed by Boris Blank (keyboards, sampling, percussion, backing vocals) and Carlos Perón (tapes) in the late 1970s. Dieter Me...
 
user228700
2:51 AM
:-)
 
Jan
I was actually thinking of this (in German):
Die Yello Strom GmbH ist eine bundesweite Vertriebs- und Marketinggesellschaft (Energiediscounter) für Energie und energienahe Dienstleistungen. Ihr Geschäftszweck ist der Vertrieb von Energie und energienahen Dienstleistungen für Privat- und Gewerbekunden. Die Yello Strom GmbH ist ein Unternehmen der EnBW Energie Baden-Württemberg AG. == Unternehmensgeschichte == Mit der Liberalisierung des Energiemarktes 1998 wurden die deutschen Versorgungsmonopole aufgebrochen. Leitungsnetze, die nach wie vor ein natürliches Monopol darstellen, müssen seitdem allen Stromlieferanten – auch denjenigen ohne eigene…
 
user228700
I want to ask it again, because the given answer is terrible but still has four upvotes!
 
Jan
I don’t know, sorry =C
 
@Kaumudi You can put a bounty on it.
Or you can edit it to bump it to main page
But I don't know the answer anyway.
 
Jan
Right. All literature sources that I wanted (minus the ones I couldn’t find anything for) have been added to the thesis. Tomorrow I’ve got to add/rewrite a quick paragraph and add a new image, because I found a mechanism in the literature that explains my debromination with PPh3. Let the then modified-paragraph walk past somebody who double-checks that it’s not terrible, and I can give my PI a first version to correct.
I feel scared =C
 
3:12 AM
anybody else have problems with wasting time on studying/work do to obsessive behaviours?
due*
I just spent probably 5 hours too many making a presentation, and all my notes need to follow so many rules and organizational schemes. I know I could get more done in less time, but I can't bring myself to do it.
 
@gannex Technical writing, creating new words and sentences that explain a difficult thing accurately and in detail, is hard.
Making presentation slides is no different.
I've been doing both regularly for over ten years now, and I still have work really hard to keep myself on task sometimes.
(Fun fact: I'm procrastinating from finishing up the Executive Summary on a report I'm writing right this very second!)
 
@hBy2Py Do you want some help in getting back to work? I can suspend you for 1 day.
3
 
It's something like the mental version of bench pressing five pounds over your max.
 
Oy, with how much work I've got at work... I could probably use a suspension until after Christmas....
(But, please don't?)
 
3:24 AM
You're too valuable to suspend.
 
@orthocresol I have to say, though, it's made me really happy to see how enthusiastically you've taken to your mod role & responsibilities.
Loong, too. It's a really great thing we've got here.
 
I just talk a lot. The others do all the hard work.
 
Dude.
 
Hahah :D
 
When I was on the frontpage just now, the top, like, six questions were all "modified by orthocresol ♦"
 
3:27 AM
@hBy2Py You don't want to know what happened there.
Anyway, gotta run - good luck with work ;)
 
@orthocresol <grin>, thanks!
 
I may or may not have abused mod powers on those six or so questions.
 
user228700
@orthocresol I don't have much rep. points in the first place, so I think I'll edit it, thanks! :-)
 
@Kaumudi Sure. If you really want to put a bounty, you can tell me, I have no use for rep since I'm a moderator anyway.
 
@hBy2Py I find I get way too into whatever I manage to focus myself on. I just finished writing a presentation for this fairly minor class I'm taking, while totally neglecting a bunch of huge exams I have. The presentation looks amazing, but I wish I'd done a bit more reading this weekend
 
3:31 AM
First rule of getting a crucial thing done: find something you want to do even less than the thing, and then make getting the thing done be procrastinating from the other thing. :-)
 
Good idea
 
Doesn't always work
 
I've been brocrastinating also
lost 5 lbs and upped my weight max by 5-10 lbs across the board. During the exam session.
 
Remarkable what one will do to oneself to avoid an undesirable task, eh? ;-)
 
it's not even undesirable. It's literally just that I don't want to do it because I have to do it
I think it's like my ego vs. superego duking it out
at least the presentation is good though. This bio class is going to get an earful of chemistry :P
 
3:36 AM
@gannex Ooh, that's rough. You don't want to do it b/c it's required for the class?
@gannex SUCK ORBITALS, MICROBE-LOVERS!
 
user228700
@orthocresol Oh, awesome. I will keep this in mind :-P I've edited it for now.
 
how did you think the oxygen got to the mitochondrion??!
:P
 
Hehe. You all think that cytochrome c is just this formless blob, well.
Lemme tell y'all WHAT.
 
leaks electrons mate
and it does it more if you stimulate your mitochondria with glucocorticoids
thereby fucking up your shit
 
@gannex I will now forever visualize cytochrome c as an overweight 45-year old drunk in a tank top, sloshing electron beer around the room.
 
3:42 AM
that's evolution for you.
 
user228700
This is what Wiki says:
 
user228700
> "When the deviation is great enough to cause a maximum or minimum in the vapor pressure versus composition function, it is a mathematical consequence that at that point, the vapor will have the same composition as the liquid, and so an azeotrope is the result"
 
I think I'm going to quote you in my presentation tomorrow morning @hBy2Py
 
<bows>
 
user228700
"Mathematical consequence"? O.o
 
3:43 AM
I hate clip art but if you can find a clip art of an overweight 45-year old drunk in a tank top, I WILL put it on my slide
ah the old "mathematical consequence argument". Everything is so clear now.
@hBy2Py
@Kaumudi
 
It's not clip art, but
 
OK. Done.
 
...
Oh my. What have I done?
 
user228700
@gannex I hate that too.
 
@Kaumudi I'm not sure which figure you're looking at
But the ones here are easier to see the behavior:
An azeotrope or a constant boiling mixture is a mixture of two or more liquids whose proportions cannot be altered by simple distillation. This happens because when an azeotrope is boiled, the vapour has the same proportions of constituents as the unboiled mixture. Because their composition is unchanged by distillation, azeotropes are also called (especially in older texts) constant boiling mixtures. The word azeotrope is derived from the Greek words ζέειν (boil) and τρόπος (turning) combined with the prefix α- (no) to give the overall meaning, "no change on boiling". The term "azeotrope" was coined...
(in the Types section)
Normally you have a nice open envelope on the temperature-vs-composition phase diagram
 
user228700
3:48 AM
I'm confused as to why the composition doesn't change when boiled at a certain composition.
 
user228700
I do understand why the positive/negative deviations are exhibited.
 
my presentation was too nice. It needed some fucking up.
 
Ok. So, how about we take this figure:
Specifically the left panel.
If you're at, say, 0.3 mole fraction of formate
and 379 K
the system will behave like a "normal" phase diagram
 
user228700
Right...
 
In this case, the vapor will be leaner in formic acid, the liquid richer
 
user228700
3:51 AM
Yes...
 
If you keep taking vapor off the top, but total recycle the liquid, the overall composition of the total system will get richer in formic acid, since the vapor is lean relative to the system average.
 
user228700
Yeah...
 
So, your system average composition will shift rightward on the diagram
 
@gannex That.... I... can I write a letter of apology to the prof?
 
3:53 AM
sure
 
user228700
Riight...
 
@Kaumudi Eventually, you'll approach the azeotrope at ~0.58 mole fraction formic acid or so.
 
user228700
Yep...
 
I actually have a folder in my gmail of unsent drafts of sarcastic apology letters
 
Due to the azeotrope behavior, as you approach that point, the composition of the liquid and of the vapor (their respective mole fractions of formic acid) will start to approach one another.
 
user228700
3:54 AM
^ Why? That was my initial question.
 
¯\_(ツ)_/¯
 
user228700
:-O I was hoping for answers!
 
Ah, I should have read your initial question, then.
Sorry!
 
user228700
:'-( OK. Thanks for trying :-)
 
I've always assumed, intuitively, that it's approximately similar to hygroscopicity.
Take MgCl2, for example
If you put some solid MgCl2 on a lab bench in ambient air, it will turn into a little blob of liquid and just sit there. Forever.
It won't take up water indefinitely and end up super-dilute.
It won't toss off water and dry up into a solid salt, like NaCl (e.g.) does
For whatever particular chemical reasons, it likes to be aquated, and at a particular concentration.
 
user228700
3:58 AM
OK...
 
Similarly, formic acid and water just naturally are groovy together at 58 mol%, for whatever reason
Similarly ethanol at ... 94%, I think it is?
 
user228700
Yeah :-|
 
user228700
95.6%
 
One of many things I only know to within one and a half sigfigs. :-)
 
user228700
OK, thanks :-) JR might know so I'll ask him too, when he comes.
 
4:00 AM
<nod>, I'm not a Real Chemist™, but a chemical engineer, so there may be some Real Chemists™ that have a more satisfying answer for you.
 
user228700
JR is a colloid scientist, really :-P
 
hehe
Yeah, that part of thermo generally always kind of annoyed me, because it seemed like a lot of the time stuff just sorta happened, and I was expected to just take it on authority.
 
user228700
Yeah :-/
 
@gannex Although... the more I look at your slide, here, the more convinced I am that the analogy is apt, especially in this context -- incidental ROS damage &c.
 
well the thing is the cy c also both oxidizes and reduces oxygen in some cases, just as the drunk both spills his beer, and pours new beers
 
4:10 AM
@gannex It makes perfect sense ... but I just can't shake the feeling that I've committed some sort of heinous scientific blasphemy.
Ok, bedtime. 'night all!
 
hmmm I saw a new paper and now I'm questioning what I was thinking about glucocorticoid receptors and enhanced mitochondrion functioning. Apparently acute stress enhances the function but chronic stress reduces it (and my presentation relates more to long term stress), so maybe the argument that GC -> mitochondria -> greater ROS concentration is not a good one...
 
 
3 hours later…
7:31 AM
has anyone read either "Process Chemistry in the Pharmaceutical Industry", "Pharmaceutical Process Chemistry for Synthesis: Rethinking the Routes to Scale-Up", or "Practical Process Research and Development – A guide for Organic Chemists" ?
 
Sorry, nope.
 
8:22 AM
A woman in Russia has been given a 7-year jail term for sending a single SMS message in spring 2008, telling a friend that she sees Russian army vehicles openly transported to the Georgian border via a railroad. They scanned the SMS database in 2015 and arrested her
 
9:07 AM
Scary stuff
The NSA in the US does similar stuff no doubt... they just don't publicize it
 
 
2 hours later…
11:08 AM
Does anyone know anything about where M.A.R. went? He can't be pinged, so it must be a while that he left...
 
cool, thanks
 
12:05 PM
@gannex Stress --> ... --> ... --> greater ROS I think is pretty well established.
It's just the question of exactly what lies between
 
 
1 hour later…
1:06 PM
Yes. This is my issue. @hBy2Py in cultured brain cell models, there is evidence it can be attributed to NOX2 and GPx expression, but mitochondrial regulation would also be expected to be implicated (it's the classic ROS source), however the relationship between glucocorticoid and mitochondrial activity is nonlinear. Stress -> -> -> ROS is a very complicated relationship
 
@Loong Yup, answering nomenclature questions is a thankless endeavor. I know, because I don't recall ever having thanked anyone who solved them for me ._.
Ich stehe bei mein Kamerade. ^_^
@ortho \o/
 
1:45 PM
Hey @para
 
@gannex My PhD research was to build and model small (~100mL) reactors for precisely controlled delivery of NO and NO2 to aqueous media, for toxicology studies.
 
@ortho called me "para"! :O ( Sheds tears of joy )
Hey Brian! o/ :3
 
Between when I started and when I finished, the best understanding of the NOx toxicology and related biomarkers changed pretty dramatically.
'allo!
 
^_^
 
1:57 PM
@ortho Currently wondering if I should change my user name to Germanium @Jan-nide
 
2:22 PM
making Si-C bonds with artificial selected cytochrome c
 
2:38 PM
@paracresol I don't get it. :(
 
2:53 PM
Ah, never mind .-.
Hey @ortho, since I'm relatively new here, I wouldn't know, but...has Silent Bob ever engaged in a conversation here? o_o
 
Dec 1 at 13:53, by Bob
@MAFIA36790 shhhhhh
 
@Loong I've already seen that X'D. But that doesn't really count as a conversation now, does it? 3;)
 
(╯°ਊ°)╯︵⊥ɐsǝꞁ
 
3:15 PM
I miss @Jan...a lot these days. :'(
 
 
3 hours later…
5:55 PM
Really?
0
Q: pre test chem 151

Guillermo Torres When aluminum is made from bauxite, aluminum oxide is reacted with carbon formin carbon dioxide and aluminum metal. a. Write a balanced equation for this reaction. b. How many g of aluminum is formed from 1000g of aluminum oxide? c. How many g of carbon is used with 1000g of aluminum oxide? ...

I mean, really.
 
@Chemobot !greet/anonymous2
 
@MelanieShebel I almost feel bad closing it. It must have taken a while to write that out
2
Only almost though
 
Hmm, @anonymous2 Hello!
@MelanieShebel Wow ;)
 
@Mithoron Hi!
 
@anonymous2 You wanted to impregnate those poor buckyballs! How could you ;D
 
6:06 PM
@Mithoron Lol, was just quoting from some article I saw in my research. Parrot, you know.
@MelanieShebel This looks like a direct quote from here.
@ringo Probably just copy-paste.
 
@anonymous2 No pity then ;)
 
Right. :)
@Mithoron I've cleared it up a bit. I do like the terms "doping" and "encapsulating" much better. :)
 
@anonymous2 Oh no, now you want to dope them ;D
 
@Mithoron Rofl, well, I guess that doesn't sound much better, but at least it is a technical scientific term.
 
@hBy2Py Huh?
 
6:14 PM
Exactly what I was going to type. :)
 
@Mithoron Was pinging ortho and Mart about some comments here:
3
A: absurd edit war

orthocresolLeaving the tone of the question aside there is a series of misconceptions or misinformation that I wish to point out. As a moderator, one might think that I am biased, but I will let the community judge what I write. Here's a quick recap [...] A moderator deleted the second phrasing of th...

But it's ortho's post, and Mart wasn't involved.
So, pointless to ping.
Just forget I was ever even here....
 
Lol. No worries, I've done worse before.
 
@anonymous2 I don't feel especially bad. Hopefully nobody thinks those deleted posts were profanity-laced rants against @Mith. ;-)
 
:D
 
@hBy2Py Very likely.
 
6:28 PM
@CowperKettle o/
 
Has anybody in earshot participated actively in any prior Winter Bashes?
I'm having a hard time ginning up enthusiasm for the hats.
 
@hBy2Py Your tiny snake could use a hat :D
 
@Mithoron And, done. When's it start??
I want me a Santa Claus hat for 'im.
 
@hBy2Py Link's pinned
 
Already visited.
Two. Whole. Weeks. <mourn>
 
6:32 PM
What is it, anyhow?
 
Sort of like a scavenger/treasure hunt.
The SO overlords (I think?) come up with a bunch of badge-like achievements you can unlock, and each one comes with a special "hat" (not always a hat) that you can overlay on your avatar.
 
How long does it last?
 
Couple weeks?
Google turns up lots of links related to last year's.
 
Winter Bash will run from 19 December 2016 up to and including 08 January 2017.
 
Oh, so three weeks, nice.
Is Chem.SE's hat in the ring?
(Are we large enough to be eligible?)
 
6:39 PM
Yes, almost all Stack Exchange sites participate.
 
Are beta sites eligible, OOC?
 
Yes, beta sites will have hats, too.
This was last year:
Pops on December 14, 2015
Another calendar year is ending, which can mean only one thing. It's time once again for the event that brings joy to all (with a slight helping of dismay for our friends in the southern hemisphere1): Winter Bash!
Pops on January 6, 2016
It's a new year, and another Winter Bash is behind us. Let's relive some of the highlights, and finally get to the bottom of the mysteries of the secret hats, before we close the 2015 (year)book for good!
 
6:56 PM
@Mithoron \o
 
7:49 PM
Would a reaction with ammonia and nitrobenzene have a high activation energy?
Since benzene will repel a nucleophile
 
Zhe
@MichaelHarding What reaction are you expecting?
Also unclear what you mean by "repel a nucleophile"
 
So you have NH3 and chlorobenzene, and I'm just saying a simple nucleophilic subsitution might occur to create aminobenzene.
And because the benzene ring is very electron dense, it would repel the nucleophile, that's why electrophiles often attack benzene
 
Zhe
That's a pretty crappy electrophile
 
I'm saying NH3 is a nucleophile.
And it substitutes with the Cl.
That's already on the benzene ring.
 
Zhe
The S_{N}Ar electrophiles generally have a bunch of nitro groups
 
7:53 PM
Here,
4bi
 
Zhe
Where are you going to add it?
Chloride is a leaving group
So you can do the ipso attack there
What's the leaving group in the substitution going to be?
If it's not productive, you'll just get the reverse
Nothing else will happen, if the addition happens at all
 
Cl- will be the leaving group
 
Zhe
Oh sorry
I misread what X was
I'm going to need to brood on that one for a while
 
Okay haha
 
8:09 PM
1
Q: Deviation from Raoults law: Acetone and ethanol

Dhruva PatilWhy is there a positive deviation from Raoults law for the solution of acetone and ethanol while there is a negative deviation for acetone and water? Isn't acetone-ethanol hydrogen bond stronger than acetone-acetone? If it is because ethanol-acetone is weaker than ethanol-ethanol, then there wou...

 
Zhe
9:01 PM
@MichaelHarding I can't think of a good chemical reason. Possibly ammonia is a gas, so using raw ammonia is weird...
 
 
2 hours later…
10:39 PM
only 38 views, but already 5 answers: chemistry.stackexchange.com/q/63917/7951
 

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