Pyridines and their Benzo Derivatives: Reactivity of Substituents

Dennis, N.

doi:10.1016/b978-008096518-5.00106-4

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2007

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“…The papers related to the nitrobenzopyridines have been reviewed several times (1)(2)(3)(4)(5)(6)(7)(8). Benzo[b]pyridine (quinoline) and benzo[c]pyridine (isoquinoline) are nitrated by means of mixed acid (H2SO4/HNO3).…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in the Nitrobenzopyridines

Sánchez‐Viesca¹,

Berros²

2007

Heterocyclic Communications

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The available data on the spectroscopy of the nitrobenzopyridines are insufficient, out-dated, and modern theory is missing. A careful study of the 'H-NMR spectra of these compounds revealed the existence of C-H-0-N=0 hydrogen bonds, the hydrogen being at peri position to the nitro group. The existence of these bonds explains the down-field shifts observed in the signals of the involved protons. Spectral data from the naphthalene series and from 1 O-NMR measurements, both involving the nitro group/per/'-hydrogen relation, confirmed our proposal.

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