Sciencemadness Discussion Board

Hg(II)sulfate

tsathoggua1 - 22-1-2017 at 07:59

Alright, a little problem here.

I need a small amount of a mercuric salt, (no HNO3 is available to simplify this), sufficient for an Al amalgam reduction on the scale of a couple of grams of substrate, 2-3g or so, so a minimum amount of Hg(II)

The sulfate is the easily accessible compound, as Hg metal should dissolve in conc. H2SO4. Whilst treatment of Hg(II)sulfate with HCl(g) and sublimation would do the trick, its really not something I'd want in gaseous form at all if it can be avoided.

Could Hg(II) sulfate be used for such amalgams at all? I'm dubious on that, since its reportedly somewhat unstable in H2O. And I'm not prepared to use conc. H2SO4 as a solvent for it in the intended rxn, since the substrate is available only in small quantity (5g total) and not particularly common or easy to find. Had to pay more than I'd like for that, and finding any again would likely prove difficult. The reported instability, according to wikipedia is decomposition to mercury 'subsulfate' for which no composition is given, but presumably Hg2SO4 if its used in the same sense as 'subchloride' was at one point used for calomel (note-this from some old literature primarily concerned with medicinal practice, couple of old books I have dating back from the late 1700s) so extrapolating from that is a bit....iffy at best. Probably better than the treatments often given in those days.

(favourites have to be finely divided mercury in chalk for teething babies, and HNO3 for piles..at least it would save you from pain on sitting down. But only since you wouldn't be doing it for the next few weeks:D)

How stable is Hg(II)sulfate in aqueous, acidic environment?
and since Hg(I) salts are generally much less toxic than the equivalent mercuric salt, hows about allowing the sulfate (mercuric sulfate that is) to decompose, then treating with either gaseous or 30% HCl?)

The easiest way seems to be formation of the mercuric sulfate using conc. H2SO4, Hg, and then mixture of the sulfate with excess NaCl, heating and sublimation of HgCl2. That should be doable in a stoppered 5-10ml flask, without too much escaping as vapour, outside, preferably. What temperature is required for the conversion?

I'm aware of other methods, such as using CuCl2 to activate Al, but given the substrate is only available in such limited quantity, and its needed for three separate projects (if anyone must know, hopefully it won't go down badly here, but 3-bromo-4-(1,1difluoromethoxy)-5-methoxy-beta-nitropropene and nitrostyrene, as well as the corresponding pthalimidopropiophenone) there is little room for error.

JJay - 22-1-2017 at 08:59

I am not one to speculate about mercury salts, but I seem to remember performing amalgams in high school with mercuric nitrate.

If any of these substances will or might be tested as drugs by you or others (and I'm assuming that this would be through legitimate channels; I hope I'm not wrong about this), you might want to do the reductions with, for example, sodium borohydride to ensure that there is no mercury in the final product.

[Edited on 22-1-2017 by JJay]

tsathoggua1 - 22-1-2017 at 09:45

Edit-already explained that no HNO3 or nitrate salts are currently available.

And afterthought-Surprising they let high school kids perform the likes of an amalgam reduction. Here they shat themselves at the idea of using HNO3 or HClO4 and comparing H2 production from Mg. And that was about 15 years back. I shudder to think at the level of chemophobia the poor buggers have to experience now.

I've been giving a LAH or Red-Al reduction serious thought.

it isn't exactly a huge difficulty removing Hg from Al/Hg reductions though given that the products are eventually isolated as freebases. Thorough H2O washing should remove any residual Hg.

But if it can be done without having to bugger about oven-drying glassware, distilling THF/EtOEt or worse, and of course buying the hydride reagents to begin with (at least, preparing for a LAH reduction would be more of a nuisance)

Red-Al is looking very tempting despite the price of the reagent, and the quantity needed per mol. of substrate.

This came about largely, because I've never seen the likes of a highly electronegative 3-position substitution on what would otherwise be an active 5HT2a agonist using the phenethylamine/alpha-alkylphenethylamine/cathinone backbones. Even in some modern papers looking at fluorinated phenethylamines seem to have overlooked substitution on the 3' Ph- carbon. Plenty of electron-donating substituents have been tested, but not the likes of halides, cyano, nitro or thiocyanato etc. And if it turns out a dead end, the aryl bromide can always be used as a leaving group for something more interesting.

Will probably look at assay of the alpha-methyl derivative first, since its likely to require lesser amount of the benzaldehyde and theres plenty nitroethane at hand. Difluoromescaline is known to be active in vivo, certainly in animals via head twitch assay (no, if anyone is wondering, I don't DO animal testing. And won't, either, I can see why its done, in some instances, but at the cost of selling one's soul to something worse than the devil.)

[Edited on 22-1-2017 by tsathoggua1]

unionised - 22-1-2017 at 10:01

If you add a lot of potassium iodide you can probably get the mercury sulphate into solution as [HgI4]2- for long enough to react with the aluminium.

Amos - 22-1-2017 at 10:28

You should be able to grind metallic mercury and aluminium together to get an amalgam going if you can't use a salt. Any water-soluble salt will likely work though; they should all activate the aluminium. A small amount of a chloride or iodide salt might not hurt, though.

DraconicAcid - 22-1-2017 at 10:35

Quote: Originally posted by tsathoggua1  
Here they shat themselves at the idea of using HNO3 or HClO4 and comparing H2 production from Mg.


Perchloric acid is generally a good reason, unless it's well diluted.

JJay - 22-1-2017 at 12:27

Quote: Originally posted by Amos  
You should be able to grind metallic mercury and aluminium together to get an amalgam going if you can't use a salt. Any water-soluble salt will likely work though; they should all activate the aluminium. A small amount of a chloride or iodide salt might not hurt, though.


It's a little tricky to get right, but applying mercury directly to aluminum to create an amalgam does work. I did this once in a lab, but the yields were lower than we expected.

We did amalgams a few times in high school. I've heard stories from my parents about how they held elemental mercury in their bare hands in chemistry classes, and I remember hearing my grandfather tell stories about vaporizing mercury on the stove. It's toxic, but the major problem with it is not in its acute toxicity but in that it is an enduring environmental toxin that you definitely don't want to have seeping under your baseboards.

I can understand that you might not have any HNO<sub>3</sub> on hand, but I find it very hard to believe that you can't get any nitrate salts.

tsathoggua1 - 22-1-2017 at 12:53

I can BUY WFNA or (I think) RFNA, and nitrates. I just don't actually have any on the shelves of the lab at the moment. I can obtain either but do not have them. There is a reason for this. Persecution from the authorities. Warrantlessly so. The old bill have waged a campaign such as to land me with PTSD, am currently, for a time, taking fucking benzos and, so far, I shudder to even think about how much glassware and reagents have either been destroyed or damaged beyond repair.

Keep getting accused of being a bomber. This is minus explosions whatsoever, minus actuak explosives or for that matter, precursors to explosives. In fact, been meaning to make a thread on such, because I'm really having quite major problems. I've lost Almost 10010.5 carats in burmese sapphires, due to 'dissappearance' whilst these filth rampage through the place and take things other than that which they claim to look for, and worse.

It wasn't concentrated HClO4 that was suggested, just the comparison of oxidizing acids with non-oxidizing acids. I know worse than I should what conc. HClO4 is like. I've got half a hand that looks decent because of it. That and SOCl2. The rest looks like a blowtorched piece of meat.

[Edited on 22-1-2017 by tsathoggua1]

Melgar - 22-1-2017 at 12:56

Get a gallium/indium eutectic alloy (3g of gallium to 1g of indium, melting point 15˚C), then alloy that with aluminum at a ratio of 20:1. Or just dissolve aluminum in eutectic Ga/In bit by bit to keep it bubbling. Much safer than mercury.

http://www.sciencemadness.org/talk/viewthread.php?tid=70110

If you really need HgCl2, HCl + H2O2 will do the trick. Be careful with the H2O2 though, add it drop by drop, slowly, with stirring. This produces elemental chlorine, which can dissolve in chloride solutions, similar to how bromine and iodine can do this, but to a lesser degree. If you oxidize too much of the chloride to chlorine though, it WILL come out of solution. Too much H2O2 can also result in a thermal runaway where the H2O2 all breaks down into water and oxygen at once.

[Edited on 1/22/17 by Melgar]

tsathoggua1 - 22-1-2017 at 13:13

Oh thank you! this substrate is way beyond merely precious, I acquired just what was possible, and there IS no more, without much effort.

Actually I have some galinstan alloy from a broken thermometer, but I've heard mixed results using gallium amalgam using 1P2NP as a subsrtate. The price per gram of the aldehyde being worked on is ridiculous, and as I said, I have no source of replacement, so the three experiments being worked on, HAVE to be got right first time. Or at least, one of them does. It cost me almost £80-5g and that is the entirety of available resource. Intent is to determine activity and little else. Although if it proves to be completely inert in vivo, reaction with something like NaOMe or LiOMe to salvage an otherwise useless compound.

But activity as a triple monoamine releaser/reuptake inhibibitor/5HT2a agonist is the desired result. The ONLY other similar substitution pattern I'm aware of are 3-fluoroamphetamine and fenfluramine (3-trifluoromethylamphetamine)

As far as I have been able to find out, this hasn't been synthesized before let alone put into a living multicellular creature. I'd love to know if it has btw.


I thought of H2O2. Although its another reagent I dare not even be within the same city as. Not for reason of its reactivity but because warrants can be ex post facto 'justified' with its presence. I do have a small amount of 9 and 12% left, should this prove enough I'd sooner use it than go to the slammer for its existence. With dropwise addition of H2O2 to Hg, even a 'catastrophic' brealdown of H2O2 at 12% isn't exactly what one would call much of a disaster. Only thing is, I'm as good as having offed myself already if peroxides of ANY kind are present.

Almost did more than once, and if things go to hades and back, well, there is no back. Long story, but whilst I have no particular emotion about ending, I do have my word, given to a certain stalker chick that I won't do so by my own hand (exceptional situations such as oncoming alzheimer's I discount, because she herself would pull the trigger in such a situation.

But I doubt I can withstand another unjust jail term. I'd either end myself, or kill every living thing on the block first. Long, unpleasant story, for elsewhere, so here I won't go into it.

[Edited on 22-1-2017 by tsathoggua1]

Melgar - 22-1-2017 at 13:46

Quote:
Only thing is, I'm as good as having offed myself already if peroxides of ANY kind are present.

Considering how much information you're divulging, you should probably be more worried about that being your undoing. H2O2 is particularly useful as an oxidizer in part because of how easy it is to remove from a solution. Boiling or even evaporating the solution will destroy it.

tsathoggua1 - 22-1-2017 at 14:18

Well its damn close to it already.


When your fucked, its a matter of waiting.

JJay - 22-1-2017 at 14:33

That's crazy talk, man.

Maroboduus - 23-1-2017 at 13:52

Quote: Originally posted by tsathoggua1  

Intent is to determine activity and little else. Although if it proves to be completely inert in vivo, reaction with something like NaOMe or LiOMe to salvage an otherwise useless compound.

[Edited on 22-1-2017 by tsathoggua1]


Sodium methoxide reacting with a bromine atom on a benzene ring?
Does this really work under conditions that wouldn't toast the rest of the molecule?

I'd be interested to know what the mechanism is for that reaction.
Maybe I'm off my stride today, but I'm having a hard time picturing a transition state for that at reasonable temperatures.

Would you use some unusual solvent or catalyst or something?
This could come in handy in lots of situations and I'd be glad to know about it.

tsathoggua1 - 23-1-2017 at 14:25

I meant, close to being completely fucked, not to offing myself. I'm bound by a promise, actually anyhow not to. That I intend to fulfill to the best of my ability. Extracted by, (and here is the crazy bit..) my stalker, of all people. (shes a good lass though, and vulpine as can be, and my word given to her, has kept me in one piece several other than for her, utterly, utterly miserable times in the past)

Corrosive Joeseph - 23-1-2017 at 15:15

Madness Science.jpg - 15kB


First you say you cannot get Nitrate salts and then you say you can.

If it were me, l would just use my H2SO4 to make Nitric from CAN fertillizer using this method -

http://www.sciencemadness.org/talk/viewthread.php?tid=9848

and dissolve my mercury in hot Nitric acid to make the Mercuric(II)Nitrate.

It would be MUCH better in your 'aqueous, acidic enviornment' which l'm presuming is AcOH..............

PS - Check out the video in the poo Tube link posted by Blogfast25 in the link above. It might just change yer mind..............


If you are really THAT paranoid/persecuted, DON'T DO IT.......!!!

Or just get a friend/partner/yer stalker to make the HNO3 and mercuric salt for you................ At their place

And be done with it.

You say you only need a small amount...........

Hope this helps

/CJ



[Edited on 23-1-2017 by Corrosive Joeseph]

[Edited on 23-1-2017 by Corrosive Joeseph]

tsathoggua1 - 23-1-2017 at 15:20

Oh, would that not work as I believed?

I was thinking along the lines of the Williamson ether synthesis, in something like acetonitrile, and in extremis, use of silver compounds to assist the reaction by coordinating the halide and making it a better leaving group. And there's always the option of swapping Br for I first, to again, aim for a better leaving group. And the rxn is SN2. Although I'd be all for testing the process with a not particularly valuable non-fluoride 2C nitrostyrene bearing a halide at the benzene C'3. Probably as a last step after reduction of the nitroalkene to the aminoalkane, given the propensity of the nitro moiety to act as a pseudohalide.

As for toasting the molecule...well the point of toasting 3-bromo-4-(1,1-difluoromethoxy)-5-methoxy-beta-nitropropene is one bit of data I do not wish to know, save on any other than than a mg or two.

Wouldn't the the difluoromethoxy group assist in withdrawing electron density from the aromatic ring, and encourage reactivity with an alkoxide? and of course, the bromine itself is an EWG,

A modified Ullmann-like reaction could do it I believe, using the alcohol rather than the alkoxide, even. Ullmann rxns classically require pretty rough conditions, which of course must be avoided with a very limitedly available and most costly substrate, but there is an Ullmann-like reaction that utilizes a catalyst, bis-bipyridylcopper(I)tetrafluoroborate, that is stated to work with aryl bromides, coupling with either phenols to afford diaryl ethers or aliphatic alcohols to give the corresponding aliphatic alcohol ether. Question is how to obtain or prepare the 2,2-bipyridyl for synthesis of the catalyst., and it seems to be a reaction that rather likes potassium bases, such as the carbonate in preference to either sodium or caesium carbonate.

Please don't mind me btw, I haven't completely finished reading the paper, will do so tomorrow, its just that my current availability of internet capability is limited in time.

https://sci-hub.ac/10.1021/jo801002c

Looks pretty nifty from what I've read thus far of it, high yields, and milder temperatures by far than the original Ullmann.

Although I'd still try it on something other than this 3-bromo-4-(1,1-difluoromethoxy)-5-MeO TMA and the corresponding bromodifluoromethoxymescaline derivative first. And in any case, I'll likely have my work cut out for me so to speak since addition of difluoromescaline to the project (phenethylamine, pthalimidopropiophenone as an acid-labile protected primary aminoketone and the corresponding TMA. With the TMA going first, to determine activity with the least weight of material required. Theres plenty nitroethane to hand but would otherwise have to buy, beg, borrow or synth nitromethane for the phen.

And its a backup plan also, in case all goes to perdition in a handbasket. That way it can be salvaged and difluoromescaline and other 3' ethers, thioethers et cetera can be replacements for the bromine. Difluoromescaline itself is known to be active and much more potent than mescaline itself from a study read a little while back, somewhere in the region of 50-60mg or thereabouts in a human. So chances are if the aryl bromide is active then the TMA version is going to be easier to know if there is any potential for a winner lurking as yet unsynthesized and untasted by man, or even animals or via patch-clamp, for all I've been able to find.

What that bromide is going to do however is anybody's guess. And if nothing else, theres the potential for DFM, much learning to be had, and plenty chemistry to get down to. Which is what suits Tsath' best.

https://sci-hub.ac/10.1021/jo801002c
10.1021/jo801002c
An Efficient Ullmann-Type C-O Bond
Formation Catalyzed by an Air-Stable
Copper(I) Bipyridyl Complex

tsathoggua1 - 23-1-2017 at 15:22

I said I can GET nitric and nitrates, but don't actually currently possess any of either, upon mine own reagent shelves. I do not see how these two states are mutually exclusive. Just means I haven't got something I am yet able to obtain should I make the effort to do so and pay the cost of reagents/shipping etc.

JJay - 23-1-2017 at 15:32

Seeing how I don't handle a lot of precious metals or make explosives, I actually don't have any nitric acid either, but I can't imagine a lab without any nitrates. Nitric acid definitely has many uses in chemistry aside from those, and should I require any, I want a means to make some readily at hand. You can easily buy nitrates at drugstores/hardware stores/garden stores/etc. If you try to buy a truckload or ask the pharmacist for some saltpeter in the middle of the night while wearing your Unibomber hoodie with a floppy hat and dark sunglasses with KMFDM logos and swastikas emblazoned all over your candy raver backpack, you might draw some unwanted attention, especially if you are wearing baggy pants, but... if nothing else, you could extract some from black powder, which, last I checked, is freely available in most places for operating antique firearms. You're telling me you're not allowed to own a muzzleloader?


[Edited on 24-1-2017 by JJay]

Maroboduus - 23-1-2017 at 15:59

I've got to admit that I'm far from the best person around here for an opinion on these things, but I suspect the Ullman would be a better bet than the Williamson synthesis.

SN2 reactions ,I think, would be pretty tough to get on a benzene ring because of it's rigidity.

I wasn't familiar with that Ullman reaction (been a long time since I had a chemistry course, and never had too many), but it sounds interesting. Thanks for the reference.

BTW: I Have seen old references to making mercuric chloride by sublimating mercuric sulfate with salt. But I don't recall if this can be done at glassware-safe temperatures. It's a real old-timey alchemist procedure.

And personally, vaporizing mercury compounds makes me a little nervous.





Corrosive Joeseph - 23-1-2017 at 16:03

Some more snippets of information.................

https://erowid.org/archive/rhodium/chemistry/mercurychloride...


/CJ

Corrosive Joeseph - 23-1-2017 at 16:08

Some more snippets of information.................

https://erowid.org/archive/rhodium/chemistry/mercurychloride...

http://chemistry.mdma.ch/hiveboard/methods/000217141.html

You'll have to sort the wheat from the chaff though...............

/CJ

[edit] - B@lls, screwed up editing my reply
Will a mod please remove my double post (the one above)

[Edited on 24-1-2017 by Corrosive Joeseph]

[Edited on 24-1-2017 by Corrosive Joeseph]

[Edited on 24-1-2017 by Corrosive Joeseph]

tsathoggua1 - 24-1-2017 at 12:53

I'm not sure about the laws here currently as they now stand, post theresa psycho-bitch may in the PM's seat. But as it stood, one could own (bearing in mind, this is only going from old memory) blackpowder muzzle-loaders, without a license, but only genuine antique pieces, there, assuming the law is the same from the last time I had reason of any kind to look it up, was a specific date of manufacture that the antique firearm had to be manufactured prior to.

And as for buying black powder in the UK...that would probably be difficult, and seasonal fireworks aside, fairly sure a license is needed for storage and security and such.

As for, your jokingly talking of asking a pharmacist for saltpeter in the middle of the night in my unabomber outfit, I'm not located in the US, where from the description that sounds like, especially given the reference to that particular fruitbin, here things are getting pretty seriously shit. Well no, they got there some time ago, but now many pharmacies won't sell acetone in the unadulterated (save any H2O content) kind commonly stocked in quantities of more than a single 50ml bottle at a time. Getting solvents is one of the more difficult problems personally in the UK at the moment.

Its down to ridiculous degrees of chemophobia. They for example (in the same outlet, one excuse after the other), refused to sell a second bottle of acetone 'because its a solvent' 'because its flammable' 'because you might accidentally DRINK it' and finally after more utter inanity in that vein, and by which time I'd had quite enough of it, it was embarrassing to watch them floundering like a live eel in a bucket of superglue, tried reason one last time, after which they came out with 'because its dangerous to children in the house'

And restated the same, AFTER mind you, they had been told that there are no children in the house, or indeed the family and nor are there any non-familial adults who have ever had reason to bring a child into the house. And that the youngest non-familial household visitors are the postman, milk-man and windowcleaners usually, and if they go breaking into somebody's house and drinking the contents of small bottles at random, then quite frankly what they'd get is pretty much what they would deserve. (not least a darwin award, although the latter was not mentioned, since its highly unlikely such imbeciles would have heard of them, else they might think a little more carefully before allowing such idiocy to pollute my range of hearing.)

One excuse after another, like a desperate man windmilling their arms at the edge of a cliff, crumbling away underneath their feet.

And this same place would have sold nail crappy nail polish remover in something like 200-300ml bottles, consisting of acetone, EtOAc, bitrex, dyes, H2O and other rubbish like castor oil without question. But just because the kind asked for was clean and most likely primarily because it had the word 'acetone' in plain print on a brown glass bottle, they threw a huge shit-fit. Some sort of claimed regulations about not being able to sell more than one of any item, bar the likes of sticking plasters, cotton wool (even then...I have my doubts about the cotton wool. And I am only half-joking), without refusing.

Candy is about the ONLY thing that isn't questioned.

Goes for completely innocuous items such as MgSO4, NaH2CO3, tiny bottles of acetone, iPA seems to have disappeared off the shelves, permanganate is rx only now, or if it isn't formally so then nobody will stock it or order on request. The attitude has deviated so far from 'serve a polite customer with politeness and discretion in return' and spun round so far as to eventually have no choice but to come full circle, or more likely, pharmacies devoid of anything but the mandatory cotton wool. Nowadays the miserable sods actively appear to look for something to use as self-'justification' to go helpfully squealing like a good, well house-broken little sheep to the nearest butcher to let them know they forgot to lock the paddock door and their sheep are escaping.

Its enough to make a hobby chemist want to move to the US, being in the UK. I have an awful lot of sympathy for anyone else stick on this shite little rock but who has to rely on entirely OTC chemical supplies. What is on offer these days is frankly, unsuitable even for a child's first chemistry set. And asking for what there IS is too easy to land you in hot water if one needs more than one kind of item or more units of the same item than one. If its even vaguely like 'chemicals'. Unless its actual food, then good luck. Some pharmacies are worse than others. Almost all are run by people who wouldn't know common sense or logical thinking if beaten half to death with a bat carved from common sense-tree-wood.

The reasoning for wishing, to go via Hg(II) sulfate to HgCl2

JJay - 24-1-2017 at 13:17

It does sound like chemicals are pretty restricted in the UK. I don't think I have seen acetone at pharmacies, but it is available here at most every department store in 4L jugs. I'm sure it has bitrex in it. Generally speaking, pharmacies are pretty unsatisfying places to buy chemicals. Controlled substances aside, some of them will sell you whatever you want (showing up in a suit and tie helps), but their selection usually isn't that great and the prices are high.

It's desperate times when you have to dry distill eggshells and vinegar to get some acetone... permanganate is hard to find OTC here but is available if you look hard enough.

I really don't know if mercuric sulfate would work for making amalgams. I suspect it would, but I doubt it works as well or conveniently as mercuric chloride or mercuric nitrate. If I were reducing a valuable substrate, I certainly wouldn't try a mercuric sulfate amalgam without testing it on something else first.


[Edited on 24-1-2017 by JJay]

Melgar - 25-1-2017 at 10:27

Even 3% H2O2 should be able to react with HCl to generate chlorine and Cl3- ions, which can oxidize metallic Hg. Do they sell that in England? I have a gallon of 30%, and you definitely have to be careful with that, but the concentrations you have would be less likely to result in a thermal runaway, since there would be a larger volume of liquid to absorb the heat that would be generated. Also, as the metal forms chloride salts, the chances drop of chlorine coming out of solution, because you also have the chloride from the metal salts reversibly forming Cl3- ions. I've been dissolving gallium using such a method, alternating between adding HCl and 30% H2O2, and even though the solution quickly reaches temperatures too hot to touch without producing many bubbles, once there was a significant amount of Ga +3 ions in solution, it completely stopped producing any chlorine odor no matter how hot it became, or how vigorous the reaction seemed to get. Granted, this is for Ga, which is much more reactive, but I had the same experience making CuCl2 and PdCl2.

tsathoggua1 - 26-1-2017 at 13:22

Yes, maximum OTC concentration is I think, either 9 or 12%, I forget which.

Its not so much as that, but the reason isn't safety in terms of bodily injury. I'm comfortable working with it at higher concentrations, its just that even owning a solution so dilute one would need it in dH2O and use NMR to even detect it, is the dangerous part (not that I have an NMR, santa isn't that generous and nor is my income. Must be those superconducting magnets screwing up raindeer navigation, if magic reindeer navigate like pigeons with the crystals of magnetite within their beak [or is it brain, I forget which]:D)

its political. Just the word 'peroxide' these days can be and in my case HAS been used to trigger persecution. And yes, I meant 'persecution' rather than 'prosecution'