Examination of some effects of NO/sub 2/ rotation in nitrobenzene

Journal Article · Tue Mar 31 23:00:00 EST 1987 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00241a002· OSTI ID:6510160

Politzer, P; Lane, P; Jayasuriya, K; Domelsmith, L N

A computational analysis has been made of some of the effects of rotating the NO/sub 2/ group of nitrobenzene by 90/sup 0/ from its equilibrium position in the plane of the aromatic ring. An ab initio SCF approach was used to compute the optimized structures and molecular electrostatic potentials of these two forms of nitrobenzene. A comparison of the calculated structures indicates that there is only a very small degree of conjugation between the nitro group and the aromatic ring in the equilibrium form of the molecule. Chemical consequences of NO/sub 2/ rotation are expected to include a decreased reactivity toward nucleophiles, but a slightly greater susceptibility to electrophilic attack.

• Research Organization: Univ. of New Orleans, LA
• OSTI ID: 6510160
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 109:7; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
CALCULATION METHODS
CHALCOGENIDES
DATA
INFORMATION
MOLECULAR STRUCTURE
MOTION
NITRO COMPOUNDS
NITROBENZENE
NITROGEN COMPOUNDS
NITROGEN DIOXIDE
NITROGEN OXIDES
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
POTENTIALS
ROTATION
SELF-CONSISTENT FIELD
STEREOCHEMISTRY
THEORETICAL DATA