Sultam and Sultim Structures, Part 3. Strong and Weak Hydrogen Bonds in 3-Oxosultams, 3-Oxosultims and 3-Alkoxysultams

Abstract

In order to study hydrogen bonding networks in cyclic sulfin- and sulfonamides, X-ray structures were determined for 3-oxosultams 3a, c - e, 3-alkoxysultams 5b, f and 3-oxosultim 2f, all of which show predominantly weak intermolecular hydrogen bonds. The 3-oxosultam 3a forms tetrameric units by combining two symmetry-independent molecules through weak aromatic C-H· · ·O-S-O hydrogen bonds without participation of the carbonyl groups. The 3-oxosultam 3c, with two chloro substituents in the N-aryl ring show a polymer arrangement of the molecules through intermolecular association of the SO2 and CO groups also with the aromatic H-atoms of the aryl rings. Sultam 3d shows the first polymer chain in the 3-oxosultam series by the strong O-H· · ·O=C hydrogen bonds without participation of the SO2 group. Two new ‘head-to-head’ dimers with a 10-membered ring are found for 3-alkoxysultams 5b, 5f through weak C-H· · ·O-S-O hydrogen bonds. In the 3-oxosultim 2f weak intermolecular hydrogen bonds are observed to form a two-dimensional network with the two methylene groups, the carbonyl function and the chloro atom but, surprisingly, without the strong S-oxide acceptor group.

N-Benzyltetrahydropyrido-anellated thiophene derivatives: new anticholinesterases

“…2 and detailed in Table 2. The values of the HÐA and DÁ Á ÁA distances, as well as the DÐHÁ Á ÁA angle, characterize these nearly linear hydrogen bonds (DÐHÁ Á ÁA = 159 and 160 ) as weak ones (Desiraju, 1996;Desiraju & Steiner, 1999;Steiner, 2002) and agree with data described in the literature (Cox, 2002;Pigge et al, 1999;Schulze et al, 2005;Vasu et al, 2004).…”

Crystal structure of rac-cis-N-(2,4-dinitrophenyl)-3,4-diphenyl-5H-1,2-oxathiol- 5-amine 2-oxide, C21H15N3O6S, sultim and sultam structures – part 4

“…The oxidation of monocyclic and bicyclic isothiazolium salts has been research intensively since the last years [1][2][3][4][5][6][7] and can be classified in two principle oxidation methods. Atfirst, the salts can be oxidized with H 2 O 2 in acetic acid to yield 3-hydroperoxysultims rac-cis/ trans,s ultams and 3-oxosultams [1][2][3][4][5].…”

“…Atfirst, the salts can be oxidized with H 2 O 2 in acetic acid to yield 3-hydroperoxysultims rac-cis/ trans,s ultams and 3-oxosultams [1][2][3][4][5]. Furthermore, the isothiazolium salts reacted with magnesium monoperoxyphthalate (MMPP)inwater or alcohol to obtain the 3-hydroxysultims rac-cis/ trans,sultams or 3-alkoxysultams [6,7].…”

N-Phenyladamantane-1-sulfinamide

“…For literature on N-alkylalkanesulfinamides, see: Sato et al (1975), Schuckmann et al (1978); Ferreira et al (2005). For related literature on cyclic N-arylalkanesulfinamides (sultims), see: Schulze et al (2005). For the synthesis, see: Stretter et al (1969).…”