This is a follow-up to the post on exploring the directing influence of (electron donating) substituents on benzene[cite]10.1021/acs.jchemed.5b00346[/cite] with the focus on heteroaromatic rings such indoles, pyrroles and group 16 analogues (furans, thiophenes etc).
Posts Tagged ‘benzo’
Exploring the electrophilic directing influence of heteroaromatic rings using crystal structure data mining.
Tuesday, June 21st, 2016Understanding the electrophilic aromatic substitution of indole.
Sunday, March 3rd, 2013The electrophilic substitution of indoles is a staple of any course on organic chemistry. Indoles also hold a soft-spot for me, since I synthesized not a few as part of my Ph.D. studies.[cite]10.1039/P29750001209[/cite],[cite]10.1039/P29770000281[/cite] The preference for substitution in the 3-position is normally explained using the arrows shown below (position 3=green,2=blue,1=red). Here I explore how these arrows might be interpreted in terms of various quantum mechanical properties.