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Paper | Special issue | Vol 35, No. 1, 1993, pp.171-180
Published online, 1st January, 1970
DOI: 10.3987/COM-92-S3
Long Range Transmission of Polar Effects in Cholinergic 3-Arylideneanabaseines. Conformations Calculated by Molecular Modelling

John A. Zoltewicz,* Katalin Prokai-Tatrai, Linda B. Bloom, and William R. Kem

*Department of Chemistry, University of Florida, Gainesville, FL 32611-2046, U.S.A.

Abstract

Benzylidene products resulting from acid-catalyzed aldol condensations of aryl aldehydes and anabaseine at position 3 of the tetrahydropyridine ring have E stereochemistry. In spite of a chemical shift scale ranging only over 0.11 ppm the methylene protons (H-6) adjacent to the imino group of the tetrahydropyridine ring show an excellent Hammett correlation using σM and σP values. Methoxy and chloro groups in an ortho position require a σI parameter. Substrates with one or two ortho methyl groups deviate. AM1 and MM2 calculations indicate that both the phenyl and pyridyl rings are twisted out of a common plane defined by the central ring.