138451-20-4Relevant academic research and scientific papers
STRUCTURE, NATURE OF HYDROGEN BONDING, AND ZE STEREODYNAMICS OF o-INDOPHENOLS
Olekhnovich, L. P.,Furmanova, N. G.,Lyubchenko, S. N.,Rekhlova, O. Yu.,Lesin, A. V.,et al.
, p. 545 - 552 (1991)
X-ray diffraction analysis was used to determine the structure of o-indophenol, C20H24N2O4 (R=0.054 relative to 4281 reflections).The crystal consists of dimers, which form hydrogen bonds with intra- and intermolecular components.IR and PMR spectroscopy shows that the formation of intra- and intermolecular O-H ...N hydrogen bonds by o-indophenol molecules depends on their aggregate state (crystalline state in solution) and steric and electronic effects of the substituent in the phenolic fragment.The p-quinonimine and phenol rings are acoplanar in dimers with intermolecular hydrogen bonds.All the o-indophenols in solution form intramolecular hydrogen bonds with coplanar or almost coplanar conformation of the quinonimine and phenol fragments.The strength of the intramolecular hydrogen bonds determines the predominance of a torsion (T) or inversion (I) mechanism for the degenerate Z E isomerization of o-indophenols or the replacement of the I and T channels for stereoconversion upon change in the solution temperature.
