4 ms·
I knew that cyclobutane existed (a ring of four carbon atoms with attached hydrogen atoms which is 'weird' in the sense that the angles between the bonds are no
by _Microft 5y ago
I knew that cyclobutane existed (a ring of four carbon atoms with attached hydrogen atoms which is 'weird' in the sense that the angles between the bonds are not what would be expected for a carbon atom with four bonds [0]) but learned about the existence of ladderanes today. Their structure looks just soo unusual.
https://en.wikipedia.org/wiki/Ladderane https://en.wikipedia.org/wiki/Ladderane
Speaking of unusual structures, here is something like a 2D version of a ladderane:
https://en.wikipedia.org/wiki/Fenestrane https://en.wikipedia.org/wiki/Fenestrane
[0] https://en.wikipedia.org/wiki/Orbital_hybridisation#sp3 https://en.wikipedia.org/wiki/Orbital_hybridisation#sp3
- jihadjihad 5y agoIt's interesting that one group of compounds is named using the Latin, in this case for "window" (fenestrane), but "ladderane" makes use of an ordinary English word (by way of Old English and Germanic). I guess I would have expected a Latin-derived name like "escalane" instead.
- _Microft 5y agoFollow the first link/s in these articles and somewhere you will find „jawsamycin“. A part of this molecule looks a lot like a row of teeth…
- ray__ 5y agoThe common names for compounds/compound classes like this are usually just left to the person that discovers them. The standardized naming scheme is set by the IUPAC and the name that you get for any reasonably complicated molecule will be a mouthful.
- gilleain 5y agoA mouthful? You're not wrong ... https://www.ebi.ac.uk/chebi/searchId.do?chebiId=132927 https://www.ebi.ac.uk/chebi/searchId.do?chebiId=132927 "8-[(1S,2R,3R,4S,6S,7S,8S,9S,12R)-pentacyclo[6.4.0.0^2,7.0^3,6.0^9,12]dodecan-4-yl]octanoic acid" Not sure how I would format the ring closure notation (like 0^2,7 is meant to be superscript)
- kccqzy 5y agoAnd the last example from the article, a tetrasubstituted cyclobutane, probably tells you that the functional groups connected to the cyclobutane could alleviate some of the ring strain in plain cyclobutane. Similarly, cyclopropane also has incredible ring strain and likely won't be found in nature, but plenty of derivatives can.
- jamesash 5y agoInterestingly, cyclobutane and cyclopropane do not have a large difference in ring strain (within about 4% of each other). Cyclopropanes are well known in natural product structures. One of the weirdest is this natural product, U-106305, which has 6 cyclopropanes. Made by a strain of Streptomyces! https://pubs.acs.org/doi/pdf/10.1021/ja9619420 https://pubs.acs.org/doi/pdf/10.1021/ja9619420
- divbzero 5y agoI glanced at the structures first before reading the text and assumed they were oddballs synthesized in the lab. It’s incredible that these are all natural products. Leptocillin also looks astonishingly weird.
- derefr 5y ago> here is something like a 2D version of a ladderane Don't know about that analogy. To me, the 3D version of a fenestrane wouldn't be a ladderane, but rather an https://en.wikipedia.org/wiki/Adamantane https://en.wikipedia.org/wiki/Adamantane