Atropisomers of Cofacial Heteroaromatic Rings with Two Positive Charges. Derivatives of 1,8-Di(3‘-pyridyl)naphthalene
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (20) , 7018-7021
- https://doi.org/10.1021/jo960906g
Abstract
The two nitrogen atoms in 1,8-di(3‘-pyridyl)naphthalene were quaternized by the addition of either benzyl or methyl groups to give dications; the latter was oxidatively converted to the di(6‘-pyridone). N-Oxidation gave the mono- and di-N-oxides. All these compounds in DMSO-d6 show anti−syn atropisomerism at ambient temperatures by 1H NMR analysis; similar amounts of both diastereomers are present.Keywords
This publication has 27 references indexed in Scilit:
- Substituent Effects on the Stability of Arene−Arene Complexes: An AM1 Study of the Conformational Equilibria ofcis-1,3-DiphenylcyclohexanesThe Journal of Organic Chemistry, 1996
- Polar Interactions between Stacked π Systems in Fluorinated 1,8‐Diarylnaphthalenes: Importance of Quadrupole Moments in Molecular RecognitionAngewandte Chemie International Edition in English, 1995
- Arene—Arene Interactions: Electrostatic or Charge Transfer?Angewandte Chemie International Edition in English, 1993
- Dominance of polar/.pi. over charge-transfer effects in stacked phenyl interactionsJournal of the American Chemical Society, 1993
- Polar/.pi. interactions between stacked aryls in 1,8-diarylnaphthalenesJournal of the American Chemical Society, 1992
- The nature of .pi.-.pi. interactionsJournal of the American Chemical Society, 1990
- Physicochemical and Cytochemical Investigations on the Binding of Ethidium and Acridine Dyes to DNA and to Organelles in Living CellsAngewandte Chemie International Edition in English, 1986
- Structural analysis of internally crowded naphthalene derivatives. peri-DiphenylacenaphtheneThe Journal of Organic Chemistry, 1976
- Synthesis of some diphenyl and triphenyl derivatives of anthracene and naphthaleneThe Journal of Organic Chemistry, 1972
- Rotational barrier in 1,8-diarylnaphthalenesThe Journal of Organic Chemistry, 1970