Timeline for Why are peroxides unstable but disulfide bridges considered stable? Why are esters stable but thiolesters are unstable?
Current License: CC BY-SA 3.0
21 events
| when toggle format | what | by | license | comment | |
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| S Aug 5, 2017 at 18:09 | history | bounty ended | CommunityBot | ||
| S Aug 5, 2017 at 18:09 | history | notice removed | CommunityBot | ||
| Aug 4, 2017 at 14:35 | answer | added | permeakra | timeline score: 10 | |
| Aug 4, 2017 at 11:31 | answer | added | El chimisto | timeline score: -2 | |
| Aug 1, 2017 at 20:57 | comment | added | Confusedbyeverything | Like I get how esters are stable bc of how much the minor resonance structure contributes to the hybrid vs thiolesters, I guess I should word the question differently: why are peroxides unstable? | |
| Aug 1, 2017 at 20:54 | comment | added | Confusedbyeverything | The confusion arose because in my non-majors biochemistry class they said thiolesters are easily broken because the longer bonds between the carbonyl carbon and the sulfur, make the partially positive end of the carbon atom more susceptible to nucleophillic attack, and in gen chem we learned that longer bonds tend to be weaker, this makes sense... However, I do not understand why a longer bond in a disulfide bridge would somehow be MORE stable than a peroxide. I probably have a poor understanding of orbital overlap? | |
| Jul 31, 2017 at 17:48 | comment | added | orthocresol | As you can see at the top of this comment chain, I asked you a question when you first posted this, as I wanted to see what you were thinking - that way it would be easy to identify a mistake, and maybe you learn something extra along the way. But if you don't engage with people who would like to help you, then it simply makes it harder for them to help you. What you are conceptually missing has already been pointed out - it is the fact that you are comparing two very different types of bonds. | |
| Jul 31, 2017 at 17:44 | comment | added | orthocresol | The whole point is that you're comparing apples and oranges. The O-O bond is weaker than the S-S bond, so peroxides are less stable than the corresponding disulfides. But there aren't any O-O or S-S bonds in esters/thioesters, so there's no reason why the same argument should apply, and there's no "contradiction" in the fact that thioesters are more reactive than esters (which is due to poor overlap of sulfur's 3p orbital with the 2p orbitals of C=O). | |
| Jul 28, 2017 at 17:57 | comment | added | Tyberius♦ | From @Mithoron's link, I also found this chemistry.stackexchange.com/questions/47056/… which explains why s-s bonds are stronger than o-o bonds. | |
| Jul 28, 2017 at 16:57 | history | edited | Confusedbyeverything | CC BY-SA 3.0 |
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| S Jul 28, 2017 at 16:56 | history | bounty started | Confusedbyeverything | ||
| S Jul 28, 2017 at 16:56 | history | notice added | Confusedbyeverything | Canonical answer required | |
| Jul 27, 2017 at 7:47 | history | tweeted | twitter.com/StackChemistry/status/890478775431036932 | ||
| Jul 19, 2017 at 16:29 | comment | added | Mithoron | chemistry.stackexchange.com/questions/431/… | |
| Jul 19, 2017 at 16:26 | review | Close votes | |||
| Jul 20, 2017 at 2:10 | |||||
| Jul 19, 2017 at 16:24 | history | edited | jerepierre | CC BY-SA 3.0 |
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| Jul 19, 2017 at 16:03 | history | edited | Mithoron | CC BY-SA 3.0 |
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| Jul 19, 2017 at 15:47 | comment | added | Eashaan Godbole | You're trying to compare trends between -O-O- and -S-S- bonds, and -C-O-C- and -C-S-C- bonds. | |
| Jul 19, 2017 at 15:28 | comment | added | orthocresol | Why do you think the trend should be the same, though? | |
| Jul 19, 2017 at 15:23 | review | First posts | |||
| Jul 19, 2017 at 15:34 | |||||
| Jul 19, 2017 at 15:23 | history | asked | Confusedbyeverything | CC BY-SA 3.0 |