A database study of the bonding and conformation of bis-sulfonylamide/-imide moieties

Bombicz, Petra; Czugler, Mátyás; Kàlmán, Alajos; Kapovits, I.

doi:10.1107/s0108768196003977

Cited by 29 publications

(27 citation statements)

References 6 publications

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“…In Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 7/1/15 6:48 AM diesen drei ionischen Verbindungen, die Bänder oder Schichten mit Fischgratmuster bilden, zeigt das Amid jeweils annähernd Spiegelsymmetrie (Cs, "Haamadelkonformation"), in 2, wie auch in (CyNH2)2Au+ N(S02-/?-C6H4I)2- [2], eher die Symmetrie einer zweizähligen Achse (C2). Die Konformationen von Disulfonylaminen sind in ei nem Review-Artikel diskutiert worden [10].…”

Section: E In Le Itu Ngunclassified

Polysulfonylamine, CXXVIII [1]. Disulfonylamido-Gold(I)-Komplexe mit Tetrahydrothiophen als Ligand / Polysulfonylamines, CXXVIII. Disulfonylamido-gold(I) Complexes with Tetrahydrothiophene as Ligand

Ahrens

Jones

2000

Zeitschrift Für Naturforschung B

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The molecular gold(I) complexes di(methanesulfonyl)amido-/V-(tetrahydrothiophene)gold(I) (1), di(p-chlorobenzenesulfonyl)amido-/V-(tetrahydrothiophene)gold(I) (2), and di(p-iodobenzenesulfonyl) amido-/V-(tetrahydrothiophene)gold(I) (3), were synthesised from (tetrahydrothiophene) chlorogold(I) and the appropriate silver salt. Crystal structure analyses were performed for all three compounds (3 both solvent-free and as a dichloromethane solvate 3a) and revealed a variety of intermolecular contacts. Compound 1 crystallizes with four independent molecules, two of which are connected by a gold-gold interaction of 3.2869(8) Å; several short nonclassical hydrogen bonds of the form C-H · O (the shortest with H · O 2.31 A) are observed. In compound 2, cyclodimers are formed via Au · Au contacts of 3.3302(8) Å; additionally Cl · Cl contacts of 3.457(3) Å are observed. Both forms of compound 3 are characterized by Au · I contacts, somewhat longer in 3 (3.6 - 4.3 Å) than in 3a (3.4 - 3.5 Å). The di(arenesulfonyl)amide ligands in 2, 3 and 3a display approximate C2 symmetry

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Section: E In Le Itu Ngunclassified

Polysulfonylamine, CXXVIII [1]. Disulfonylamido-Gold(I)-Komplexe mit Tetrahydrothiophen als Ligand / Polysulfonylamines, CXXVIII. Disulfonylamido-gold(I) Complexes with Tetrahydrothiophene as Ligand

Ahrens

Jones

2000

Zeitschrift Für Naturforschung B

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“…The general conformational preference of Figure 9 is equally valid for bis-sulfonamides, 64 aliphatic sulfonamides, and sulfamides, and it has two important practical consequences: First, cyclic sulfonamides preferentially carry axial substituents, since only this arrangement corresponds to the preferred rotamer. This is generally the case in the CSD for cyclic sulfonamides in six-membered and larger rings (e.g., HITQOQ, Figure 11), except for those where other steric effects override this preference (YAKBOC, XOHBOL, not shown).…”

Section: Sulfonamides and Sulfonesmentioning

confidence: 99%

Small Molecule Conformational Preferences Derived from Crystal Structure Data. A Medicinal Chemistry Focused Analysis

Brameld

Kuhn

Reuter

et al. 2008

J. Chem. Inf. Model.

327

332

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Based on torsion angle distributions of frequently occurring substructures, conformation preferences of druglike molecules are presented, accompanied by a review of the relevant literature. First, the relevance of the Cambridge Structural Database (CSD) for drug design is demonstrated by comparing substructures present in compounds entering clinical trials with those found in the CSD and protein-bound ligands in the Protein Data Bank (PDB). Next, we briefly highlight preferred conformations of elementary acyclic systems, followed by a discussion of sulfonamide conformations. Due to their central role in medicinal chemistry, we discuss properties of aryl ring substituents in depth, including biaryl systems and systems of two aryl rings connected by two acyclic bonds. For a subset of torsion motifs, we also compare torsion angle histograms derived from CSD structures with those derived from ligands in the PDB. Furthermore, selected properties of some six-and seven-membered ring systems are discussed. The article closes with a section on attractive sulfuroxygen contacts.

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“…Das Anion der vorliegenden Struktur fällt mit S-N-S = 120,3 (1) • nicht aus dem Erfahrungsrahmen. Überdies zeigt es die gestreckte und gestaffelte Standardkonformation [13] mit zweizähli-ger Rotationssymmetrie um die Halbierende des S-N-S-Winkels und Anordnung der Methylgruppen auf unterschiedlichen Seiten des S-N-S-Dreiecks (nichtkristallographische Punktgruppe C 2 , s. Torsionen O/C-S-N-S und C-S··· S -C in Tab. 2, Abweichung ∆τ SN von idealer C 2 -Symmetrie ca.…”

Section: Die Asymmetrische Einheitunclassified

Polysulfonylamine, CLXXX [1]. Bis(triphenylphosphoranyliden)ammonium-di(methansulfonyl)amid: Eine Kristallstruktur mit CH/π-Wechselwirkungen zwischen Methylund Phenylgruppen / Polysulfonylamines, CLXXX [1]. Bis(triphenylphosphoranylidene)ammonium Di(methanesulfonyl)amide:A Crystal Structure Featuring Methyl-Phenyl CH/π Interactions

Wölper

Jones

Blaschette

2007

Zeitschrift Für Naturforschung B

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The structure of [Ph 3 PNPPh 3 ][(MeSO 2 ) 2 N] (monoclinic, P2 1 /c, Z = 1; single-crystal X-ray diffraction at −140 • C) displays chains of relatively small anions, surrounded by four parallel columns of bulky cations, giving a rectangular array. In contrast to a previously reported series of onium dimesylamides with smaller cations, interanion hydrogen bonding C Me -H··· O, originating from the inductively activated methyl groups, is not observed in the present structure. In consequence, the packing arrangement is determined by multiple phenyl embraces between cations, weak cation-anion hydrogen bonds C Ph -H···O/N and, most notably, by methyl-phenyl CH/π interactions between anions and cations. One methyl group forms two C-H···π contacts to different phenyl rings (hydrogen-to-centroid distances: 272 and 285 pm), the other lies in a tripodal mode above an aromatic ring plane (hydrogen-to-centroid distances: ca. 330 pm).

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A database study of the bonding and conformation of bis-sulfonylamide/-imide moieties

Cited by 29 publications

References 6 publications

Polysulfonylamine, CXXVIII [1]. Disulfonylamido-Gold(I)-Komplexe mit Tetrahydrothiophen als Ligand / Polysulfonylamines, CXXVIII. Disulfonylamido-gold(I) Complexes with Tetrahydrothiophene as Ligand

Polysulfonylamine, CXXVIII [1]. Disulfonylamido-Gold(I)-Komplexe mit Tetrahydrothiophen als Ligand / Polysulfonylamines, CXXVIII. Disulfonylamido-gold(I) Complexes with Tetrahydrothiophene as Ligand

Small Molecule Conformational Preferences Derived from Crystal Structure Data. A Medicinal Chemistry Focused Analysis

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