An examination of some effects of OH rotation in phenol and p-nitrophenol
1988; Elsevier BV; Volume: 179; Issue: 1 Linguagem: Inglês
10.1016/0166-1280(88)80140-4
ISSN1872-7999
Autores Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoA computational analysis of phenol and p-nitrophenol has been carried out with the objective of determining the extent to which the conjugation between the -OH group and the aromatic ring is affected by a 90° rotation of the former. The ab initio SCF-MO GAUSSIAN 82 procedure was used to compute optimized geometries, electronic densities and electrostatic potentials. The effect of rotation upon the structures and distributions of π electronic charge are rather small. However, the electrostatic potential reveals that as a consequence of rotation around the COH bond, there should be an overall preference for the ortho positions as the initial sites for electrophilic attack. The -NO2 group deactivates the aromatic ring toward electrophiles and increases the positive character of the hydroxyl hydrogen.
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