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An examination of some effects of OH rotation in phenol and p-nitrophenol

Publication Type : Journal Article

Thematic Areas : Center for Computational Engineering and Networking (CEN)

Source : J. Molec. Struct. (Theochem) 179, 439-449, 1988

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Campus : Coimbatore

School : School of Engineering

Center : Center for Computational Engineering and Networking, Computational Engineering and Networking

Department : Center for Computational Engineering and Networking (CEN)

Year : 1988

Abstract : A 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 COH 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.

Cite this Research Publication : Peter Politzer and N. Sukumar, “An Examination of some Effects of OH Rotation in Phenol and p-Nitrophenol”, J. Molec. Struct. (Theochem) 179, 439-449 (1988) IF: 1.545

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