Structure of 2-benzoylimino-3-methyl-1,3-thiazolidine: a comparison of intramolecular <i>X</i>–S...O = <i>Y</i> interactions

Kàlmán, Alajos; Parkanyi, L.

doi:10.1107/s056774088000876x

Cited by 28 publications

(1 citation statement)

References 14 publications

(17 reference statements)

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“…Intramolecular nonbonded interaction between sulfur and oxygen (or nitrogen) atoms has been observed in a large number of organosulfur compounds controlling the conformation of small and large molecules . In these molecules, the nonbonded S···O or S···N atoms' distances are significantly shorter than the sum of the corresponding van der Waals radii (3.32 or 3.35 Å) in the crystalline structure …”

Section: Introductionmentioning

confidence: 99%

Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds

et al. 1998

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The intramolecular nonbonded 1,5-type S···O interactions are recognized in the crystalline structures of the (acylimino)thiadiazoline derivatives (1−3) as angiotensin II receptor antagonists. The relative stability of the nonbonded 1,5-type S···O interaction was investigated using the X-ray crystallographic analyses and the ab initio MO calculations (HF/3-21G*, 6-31G*, and 6-311+G**) of the simplified model compounds (6, 7, and 9). The concept of mimic-fused bicyclic heterocycles consisting of fairly stable nonbonded S···O interaction seems to be an efficient approach toward the design and development of various drugs.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds

et al. 1998

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The Stereochemistry of Sb(III) Halides and Some Related Compounds

Sawyer¹,

Gillespie²

1986

Progress in Inorganic Chemistry

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Synthetic and Structural Studies of 1,8‐Chalcogen Naphthalene Derivatives

Knight

Fuller

Bühl

et al. 2010

Chemistry A European J

156

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Four novel 1,8-disubstituted naphthalene derivatives 4-7 that contain chalcogen atoms occupying the peri positions have been prepared and fully characterised by using X-ray crystallography, multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular distortion due to noncovalent substituent interactions was studied as a function of the bulk of the interacting chalcogen atoms and the size and nature of the alkyl group attached to them. X-ray data for 4-7 was compared to the series of known 1,8-bis(phenylchalcogeno)naphthalenes 1-3, which were themselves prepared from novel synthetic routes. A general increase in the E...E' distance was observed for molecules containing bulkier atoms at the peri positions. The decreased S...S distance from phenyl-1 and ethyl-4 analogues is ascribed to a weaker chalcogen lone pair-lone pair repulsion acting in the ethyl analogue due to the presence of two equatorial S(naphthyl) ring conformations. Two novel peri-substituted naphthalene sulfoxides of 1, Nap(O=SPh)(SPh) 8 and Nap(O=SPh)(2) 9, which contain different valence states of sulfur, were prepared and fully characterised by using X-ray crystallography and multinuclear NMR spectroscopy, IR spectroscopy and MS. Molecular structures were analysed by using naphthalene ring torsions, peri-atom displacement, splay angle magnitude, S...S interactions, aromatic ring orientations and quasi-linear O=S...S arrangements. The axial S(naphthyl) rings in 8 and 9 are unfavourable for S...S contacts due to stronger chalcogen lone pair-lone pair repulsion. Although quasi-linear O=S...S alignments suggest attractive interaction is conceivable, analysis of the B3LYP wavefunctions affords no evidence for direct bonding interactions between the S atoms.

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Structure of 2-benzoylimino-3-methyl-1,3-thiazolidine: a comparison of intramolecular X–S...O = Y interactions

Cited by 28 publications

References 14 publications

Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds

Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds

The Stereochemistry of Sb(III) Halides and Some Related Compounds

Synthetic and Structural Studies of 1,8‐Chalcogen Naphthalene Derivatives

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