8-Hydroxy-1-naphthoyl compounds

Abstract

The lactone of 8-hydroxy-1 -naphthoic acid reacts with nucleophilic reagents to give a variety of 8-hydroxy-Inaphthoyl compounds. In these an intramolecular hydrogen bond unites the hydroxy-and carbonyl functions and strongly affects ultraviolet and visible spectra, but only in non-basicsolvents. The reactions of these compounds in strong acid, and their mass spectra, are also dependent on peri-ring closures.

Structure of peri-hydroxy- and peri-methoxy-substituted aldehydes and ketones according to spectral data and quantum-chemical calculations

“…We were the first to consider the spectral parameters reported in the above publications in terms of an integrated concept based on up-to-date views on peri effects. It should be emphasized that our interpretation differs from authors' treatment of some results given in [2,3]. and its strength may be judged by variation of the carbonyl stretching vibration band (ν C=O ) in the IR spectra of solutions of these compounds in different solvents ( Table 1).…”

“…The methodology of spectral studies used in this work was proposed in [2,3]. It implies measurement of IR spectra at a low substrate concentration (0.5% for all compounds) to avoid association of molecules via intermolecular hydrogen bonding.…”

“…Naphthalene derivatives having hydroxy and carbonyl groups in the neighboring peri positions play an important role as potential precursors of peri-fused heterocyclic systems [1][2][3]. In addition, these compounds are unique models for studying so-called [4,5] "peri effects" (hydrogen bonds, electrophilic interactions, ring-chain tautomerism, and other interactions between the peri substituents) [2][3][4][5][6][7][8][9][10][11][12][13].…”

“…In addition, these compounds are unique models for studying so-called [4,5] "peri effects" (hydrogen bonds, electrophilic interactions, ring-chain tautomerism, and other interactions between the peri substituents) [2][3][4][5][6][7][8][9][10][11][12][13]. While studying the reactivity and predicting chemical properties of peri-hydroxy carbonyl compounds, it is strongly desirable to know specific features of the structure of perihydroxy carbonyl moiety and the nature of peri effects therein.…”

“…In the present work we examined the effect of the molecular rigidity determined by the presence of an ethylene or vinylene bridge on the strength of intramolecular interactions between the peri substituents in hydroxy and methoxy aldehydes and ketones of the acenaphthene and acenaphthylene series (compounds II and III) [16,17], as well in peri-substituted naphthaldehydes Ia and Ib [3] and naphthyl methyl ketones Ic and Id [2] synthesized previously, on the basis of their IR, UV, and 1 H NMR spectra, X-ray diffraction data, and quantum-chemical calculations. We were the first to consider the spectral parameters reported in the above publications in terms of an integrated concept based on up-to-date views on peri effects.…”