The Chemical EducatorISSN: 1430-4171 (electronic version) Abstract Volume 3
Issue 2 (1998), S1430-4171(98)02190-6
Pitfalls in the Application of Hückel’s RuleRichard Francis Langler Department of Chemistry, Mount Allison University, Sackville, New Brunswick
E4L 1G8 Published online: 2 April 1998 Abstract. A semicircular mnemonic is described which permits one to anticipate the Hückel eigenvalue patterns for symmetrical contiguous nonfused bicycles (e.g., biphenyl). The mnemonic constitutes a new technique that is complementary to the existing Frost circle mnemonic for hydrocarbon monocycles. Pedagogically, the development of this semicircular mnemonic in class will serve to establish that the widespread practice of applying Hückel’s rule to polycycles is unsound.
Key Words: In the Classroom; Frost circle mnemonic; aromatic bicycles; biphenyl; semicircular mnemonic; Dewar resonance energies (*) Corresponding author. (E-mail: rlangler@mta.ca) Article in PDF format (70 KB ) Issue date: April
2, 1998 |