Tuesday 6 October 2015

inorganic chemistry - Is borazine aromatic?


enter image description here


I came across this structure which has got pi bonds only in its canonical forms (which are also unstable compared to the Ist structure), is it aromatic?


Also, is it compulsory for an aromatic compound to contain a carbon ring? Can't a conjugate system without carbon be aromatic (as in this case)?



Answer



The modern definition of aromaticity from deep theoreticians is that the π-system needs to support aromatic ring currents. Borazine can support it, so it is technically aromatic.


Aromatic systems that do not contain carbon are not really all that common, but they are known. Pentazole was detected, for example. The problem is, that for aromaticity to be a thing we need a π-system, and π-systems effectively restrict us to BCNOS elements, since other elements are not eager to form π-bonds. Aromatic systems are usually 5- or 6-membered rings. Add in the fact that rings with a lot of N/O atoms often happily go kaboom after a funny look, and it's not surprising we have very few actual examples here. Still, some people insist on doing unreasonable things with results from as far back as the 50s.


No comments:

Post a Comment

readings - Appending 内 to a company name is read ない or うち?

For example, if I say マイクロソフト内のパートナーシップは強いです, is the 内 here read as うち or ない? Answer 「内」 in the form: 「Proper Noun + 内」 is always read 「ない...