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Dr. Glaser's Visualization Center
To accompany Bruice, Organic Chemistry, 3/e, Chapter 14

Theme Molecule Name Chemical Formula
Being Aromatic benzene (S) C6H6
Being Aromatic cyclobutadiene (S) C4H4
Being Aromatic cyclopropeniumyl cation (S) C3H3+
Being Aromatic cyclopentadieniumyl cation (S) C5H5+
Being Aromatic cyclopentadienyl anion (S) C5H5-
Being Aromatic cyclooctatetraene dianion (S) C8H8-
Aromatic Compounds of Interest adrenaline (S) (HO)2C6H3-CHOH-CH2NHCH3
Aromatic Compounds of Interest dioxin TCDD (S) C12H4Cl4O2
Aromatic Compounds of Interest methamphetamine (speed) (S) C6H5-CH2CHCH3-NHCH3
Aromatic Compounds of Interest saccharin (S) C6H4-CO-NH-SO2-
Electrophilic Aromatic Substitution sigma complex (S) [C6H6Cl]+

[a] Unless otherwise noted, structures were optimized at the ab initio level MP2(full)/6-31G*.
[b] Adrenaline, dioxin, speed and saccharin were optimized at the ab initio level RHF/6-31G*.
[c] Anionic reactive intermediates were optimized at the correlated level MP2(full)/6-31+G*.