Computational analysis of the reactive properties of some nitrosoaromatic molecules
The interactions of a nitroso (NO) substituent with an aromatic ring and with an amino group on that ring, and the manner in which these affect the overall molecular reactivity, have been studied by ab initio SCF molecular orbital calculations. The Gaussian 82 program was used to first optimize the structures of nitrosobenzene and the three isomeric nitrosoanilines, at the 3-21G level, and then to compute the STO-5G molecular electrostatic potentials. The NO was found to deactivate the ring toward electrophilic attack, even in the presence of NH/sub 2/, although the directing properties of the latter are evident. For each molecule, the strongest negative potential is associated with the lone pair of the nitroso nitrogen. All the molecules show buildups of positive potential above the C-NO portions, within the C-N-O angles; these are interpreted as possible routes for nucleophilic attack.
- Research Organization:
- Univ. of New Orleans, LA
- OSTI ID:
- 6542337
- Journal Information:
- J. Phys. Chem.; (United States), Journal Name: J. Phys. Chem.; (United States) Vol. 91:8; ISSN JPCHA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
AROMATICS
CHEMICAL REACTIONS
COMPUTERS
DATA
ELECTRIC FIELDS
INFORMATION
MOLECULAR ORBITAL METHOD
MOLECULAR STRUCTURE
NITROSO COMPOUNDS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SELF-CONSISTENT FIELD
THEORETICAL DATA