Long range transmission of polar effects in cholinergic 3-arylideneanabaseines. Conformations calculated by molecular modelling

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

Research output: Contribution to journalArticle

42 Scopus citations

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 σ1, 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.

Original languageEnglish
Pages (from-to)171-180
Number of pages10
JournalHeterocycles
Volume35
Issue number1
DOIs
StatePublished - 1 Jan 1993

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