Pointers%20for%20basicity

Pointers%20for%20basicity - Pointersforbasicity:

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Pointers for basicity: -You need to look for resonance: Anilines (simple resonance – electron donating or withdrawing groups in the  p-position) and funky (such as pyridines, pyrrole, imidazole types- you need to draw the protonated forms as  well and see what argument can be made). Remember resonance in p-position but in meta it is inductive  only.ie.  OCH 3 OCH 3 NH 2 NH 2 resonance electron donating inductive effect of heteroatom such as oxygen, (pulls the electrons towards itself) -You need to look for closed loops: aromatic vs nonaromatic  vs antaromatic  -Then you will look at inductive effects, electronegativity and hybridization -Finally hydrogen bonding. -If you just say resonance ( you have to show the resonance structure) -No 5-valent carbons or nitrogens are allowed. See below: N H H + N H H N H H Absolutely not allowed!!! 6 e aromatic non aromatic Plus it looks absolutely awful!! It hurts my eyes!!! Which of the nitrogens is most basic.
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This note was uploaded on 10/11/2010 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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Pointers%20for%20basicity - Pointersforbasicity:

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