NMR and IR investigations of strong intramolecular hydrogen bonds

Abstract

For the purpose of this review, strong hydrogen bonds have been defined on the basis of experimental data, such as OH stretching wavenumbers, OH, and OH chemical shifts, OH (in the latter case, after correction for ring current effects). Limits for O-H,Y systems are taken as 2800 > OH > 1800 cm1, and 19 ppm > OH > 15 ppm. Recent results as well as an account of theoretical advances are presented for a series of important classes of compounds such as -diketone enols, thioxoketone enols, Mannich bases, proton sponges, quinoline N-oxides and diacid anions. The O,O distance has long been used as a parameter for hydrogen bond strength in O-H,O systems. On a broad scale, a correlation between OH stretching wavenumbers and O,O distances is observed, as demonstrated experimentally as well as theoretically, but for substituted diketone enols this correlation is relatively weak.