ISSN:
0020-7608
Keywords:
Computational Chemistry and Molecular Modeling
;
Atomic, Molecular and Optical Physics
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The structure of 4,5-benzo-3-isothiazolone and 5-phenyl-2-(E)-styryl-3-isothiazolone have been calculated both at the semiempirical AM1 level and by using the ab initio 4-31G basis set. Neither method gives a satisfactory account of the bond lengths and angle at the sulfur atom in comparison with crystallographic data, but the inclusion of polarization functions on the sulfur atom alone gives a marked improvement in the theoretical results. The conformations, structure, and electronic properties of a series of other antifungal 3-isothiazolones have been calculated by the same method. Although structural effects do not appear to play an important role in the mechanism of the inhibition of fungi by the 3-isothiazolones described here, the electronic properties calculated in terms of the atomic charge at sulfur and the LUMO energy appear to relate to their known reactivity with nucleophiles and their observed biological activity. © 1995 John Wiley & Sons, Inc.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/qua.560550407
Permalink
