USE OF ELECTROSTATIC POTENTIALS TO STUDY NONBONDED INTRAMOLECULAR INTERACTIONS IN 1,8-DISUBSTITUTED NAPHTHALENES WITH CARBONYL GROUPS AS ELECTROPHILIC SUBSTITUENTS

Ab initio Self-Consistent Field molecular orbital calculations were ca rried out on seven 1,8-disubstituted naphthalene compounds to probe th e non-bonded intramolecular interactions between electrophilic and nuc leophilic substituents located at the 1 and 8 positions. The electroph ilic substituents were characterized by the C=O group with the carbony l carbon as the electrophilic center. The nucleophilic substituents we re amino [(CH3)(2)N-], methoxy (CH3O-) and hydroxy (-OH) groups. The n ature of the intramolecular interaction was probed by calculating the molecular electrostatic potential on the molecular surface adjacent to the substituents. Differences in net atomic charges and surface molec ular electrostatic potentials with and without an adjacent substituent showed the presence of significant non-bonded interactions between th e electrophilic and nucleophilic centers in these compounds. (C) 1998 Elsevier Science B.V. All rights reserved.