Remarkable discrepancy in the predominant structures of acyl(or thioacyl)aminothiadiazoles, acyl(or thioacyl)aminooxadiazoles and related compounds having the potential for rotational, geometrical and tautomeric isomerism
Graphic
Section snippets
Acknowledgments
This work was partly supported by a Grant-in-Aid for Scientific Research (B) (2) (No. 12470482) from the Japan Society for the Promotion of Science.
References (16)
- (a)Metzger, J. V. Comprehensive Heterocyclic Chemistry: Thiazoles and Their Benzo Derivatives; Katritzky, A. R.; Rees,...(b)Abstracts of the 5th Annual Meeting of Division of Medicinal Chemistry in Japan (Toyama),...
Biosci. Biotech. Biochem.
(1996)et al.Bioorg. Med. Chem. Lett.
(1997)et al.Bioorg. Med. Chem.
(1997) - et al.
QCPE Bull.
(1990)et al.J. Comput. Chem.
(1993) - et al.
J. Med. Chem.
(1995)et al.J. Med. Chem.
(1997)et al.Bioorg. Med. Chem.
(1997)et al.J. Org. Chem.
(1998)et al.Tetrahedron Lett.
(2001) - et al.
J. Am. Chem. Soc.
(1980)et al.J. Am. Chem. Soc.
(1990)et al.J. Org. Chem.
(1994)et al.J. Antibiot.
(1995)et al.Synlett
(1997)et al.J. Am. Chem. Soc.
(1997)et al.J. Org. Chem.
(2000) - (a)Kucsman, A.; Kapovits, I. In Organic Sulfur Chemistry: Theoretical and Experimental Advances; Bernardi, F.;... et al.
J. Am. Chem. Soc.
(1992)et al.J. Heterocycl. Chem.
(1992)et al.Can. J. Chem.
(1993)et al.Can. J. Chem.
(1998) - et al.
J. Am. Chem. Soc.
(1991) - et al.
Acta Crystallogr.
(1987) - et al.
Bull. Chem. Soc. Jpn.
(1995)
Cited by (22)
The role of weak interactions in self-assembly of supramolecular associations of benzothiazole derivatives and their coordination compounds
2018, Inorganica Chimica ActaCitation Excerpt :An example of this type of interaction is shown in the X-ray crystal structure of the lysozyme protein (PDB 6LYZ), Figure SI 1, where the distances lp(S)···π to the centroids of five membered rings are in the range of 3.9–4.4 Å. These weak interactions are relevant for some organic molecules, stabilizing a thermo-dependent conformation and restricting its rotation [23]. All these contributions are also important for maintaining folded protein structures and their thermal stability [8].
The origin and magnitude of intramolecular quasi-cyclic S...O and S...S interactions revisited: A computational study
2015, Chemical Physics LettersCitation Excerpt :The intramolecular distances were found to be much shorter in such S⋯O, S⋯S, S⋯N interactions than the sum of their corresponding van der Waal's (vdW) radii (3.32 Å, 3.60 Å and 3.35 Å, respectively) [6]. The X-ray crystallographic analyses confirm the presence of 1,5-type non-bonded S⋯O and S⋯S interactions in acylimino-benzothiazoline, thioacylimino-benzothiazoline, acylimino-thiazoline and thioacylimino-thiazoline systems (Scheme 1) [6,12–14]. The intramolecular non-bonded S⋯O, S⋯S, S⋯N interactions play a crucial role in the conformations, geometries and biological activity of several organosulfur compounds.
Investigation of simple and water assisted tautomerism in a derivative of 1,3,4-oxadiazole: A DFT study
2013, Journal of Molecular Graphics and ModellingCitation Excerpt :Tautomerism has been found to be important in the chemistry of oxadiazole family in general. Because of their importance, oxadiazoles have been the subject of some computational investigations focused mainly on their structural, electronic states, spectral, and optical properties [22–28]. Since tautomerism in the oxadiazole structures affect their chemical and biological activities, it is very important to know the complete scheme of tautomerism and the reaction pathways between different tautomers.