Abstract
Investigations into the Mechanism of Solvolysis of 3-aryloxybenzisothiazoles
Highlights
Benzisothiazoles, known as saccharins, are heterocyclic compounds with many relevant applications
The ethers investigated (6;Z = H, NO2, OCH3) have two (Z = H) and three (Z = NO2, OCH3) intramolecular rotational degrees of freedom, represented by arrows in Figure 1, that may result in different conformers. These are related with: (i) the relative orientation of the saccharyl and aryl rings (dihedral angles A and B; for dihedral A, only the zusammen (Z) orientation was considered, since conformations where the aryl ring is directed to the phenyl group of the saccharin moiety are expected to correspond to structures of high energy, due to hindrance); (ii) the relative orientation of the substituent and the aryl ring
For the unsubstituted phenoxysaccharin (6a; Z = H), the potential energy profile for internal rotation around the dihedral angle B calculated at the O3LYP/6-31++G(d,p) level revealed that in the global minimum conformation the B dihedral is −92o, i.e., the phenyl substituent is nearly perpendicular to the plane of the heterocycle
Summary
Benzisothiazoles, known as saccharins, are heterocyclic compounds with many relevant applications. The results reveal that the electronic nature of the substituent on the aryl system has very little or no effect on geometric parameters of the ether linkage, even in methanol.
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