M. Remko
Jan 9, 2003
Citations
0
Influential Citations
38
Citations
Journal
Journal of Physical Chemistry A
Abstract
The geometries of substituted sulfonamides [sulfonamide (I) sulfamic acid (II), sulfamide (III), methane sulfonamide (IV), 1,1,1-trifluoromethanesulfonamide (V), 4-aminobenzenesulfonamide (VI), 1,2-benzisothiazol-3-(2H)-one-1,1-dioxide (saccharin) (VII), N-(5-sulfamoyl-1,3,4-thiadiazol-2yl)acetamide (acetazolamide) (VIII), 4-(aminosulfonyl)-N-[(4-fluorophenyl)methyl]-benzamide (1I9L) (IX), (R)-(+)-4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,-dioxide (brinzolamide) (X), and (4S-trans)-(+)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide (dorzolamide) (XI)] in both neutral and deprotonated forms, were optimized using CBS-QB3 theory (compounds I−IV), the Becke3LYP/6-311+G(d,p) method (compounds I−VIII), and the two-layered ONIOM(B3LYP 6-311+G(d,p): MNDO) method (compounds VIII - XI). Sulfamic acid behaves in the gas phase as O-acid. The investigated acids are weak acids with calculated acidity of about 1320−1420 kJ mol-...