ChemInform Abstract: NONBONDED SULFUR‐OXYGEN INTERACTION IN ORGANIC SULFUR COMPOUNDS

Kucsman, Árpád; Kapovits, I.

doi:10.1002/chin.198552342

Cited by 18 publications

(29 citation statements)

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“…9.1a) in accord with previous observations for S· · · O [27,32] and S· · · S [29,30] interactions. However, no directional preference was observed around the O atom irrespective of whether it is involved in an amide group or other carbonyl groups ( Fig.…”

Section: Nonbonded Interactions Involving a Divalent Sulfur Atomsupporting

confidence: 93%

“…9.1b). This is in strong contrast to the observation of Kucsman and Kapovitz [32] for the intramolecular 1,4-and 1,5-S· · · O = C interactions, suggesting that the directional preference around the O atom in intermolecular S· · · O = C interactions should be very week and hence it will be easily affected by other steric and energetic factors. On the other hand, the linearity of the Y-S· · · O alignment was proved to be robust against the packing force of organic crystals.…”

Section: Nonbonded Interactions Involving a Divalent Sulfur Atomcontrasting

confidence: 83%

“…This orbital model of the weak S· · · S interactions was later supported by Desiraju and Nalini [30], whereas Dahaoui et al [31] pointed out the importance of dispersion force for the S· · · S interactions. On the other hand, the directional preference of S· · · O interactions around the O atom was studied in detail by Kucsman and Kapovitz [32]. For intramolecular 1,4-and 1,5-S· · · O = C interactions, the S atom tended to lie in the direction of the O lone pairs (i.e., the n O direction) rather than the π electrons (i.e., the π O direction), suggesting the importance of n O → σ* S orbital interaction for the stability.…”

Section: Nonbonded Interactions Involving a Divalent Sulfur Atommentioning

confidence: 99%

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Chalcogen Bonds in Protein Architecture

Iwaoka

2015

Challenges and Advances in Computational Chemistry and Physics

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Nonbonded interactions between a divalent sulfur atom and polar functional groups, i.e., S· · · X (X = O, N, and S) interactions, have recently been demonstrated to stabilize protein structures to some extent and play putative roles in their function and evolution, thanks to the interplay of statistical analysis of protein structure databases and theoretical calculation using simple molecular cluster models. The directional features observed between the interacting S and X atoms suggest that they can also be called S· · · X chalcogen bonds in analogy to halogen bonds. While the existence of chalcogen bonds in proteins may be accepted today by the protein scientist community, there are still several issues that should be addressed clearly before going forward to applications of the interactions to protein engineering and the ligand design. Herein, the current status of the research on the S· · · X chalcogen bonds in proteins is reviewed from several points of view, including the historical aspects and the analytical methods for mining chalcogen bonds in protein structures. Statistical, directional, and energetic features of four typical S· · · X chalcogen bonds in proteins are presented. Possibility of analogous Se· · · X chalcogen bonds in selenoproteins is also pointed out. Implications of S· · · X chalcogen bonds in the structural control and in the function and evolution of some particular proteins are subsequently summarized from the recent literature. Finally, it is proposed that the concept of S· · · X chalcogen bonds will be a useful tool for fully understanding not only protein structures but also the biological aspects. Thus, the chalcogen bonds, though their interaction energy is smaller than that of classical hydrogen bonds, can be an element of weak noncovalent interactions that control chemical and biological properties of protein architecture. IntroductionSulfur is involved in almost all proteins as cysteine (Cys) and methionine (Met) amino acid residues. In particular, it is contained at high concentrations in keratin

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Section: Nonbonded Interactions Involving a Divalent Sulfur Atomsupporting

confidence: 93%

Section: Nonbonded Interactions Involving a Divalent Sulfur Atomcontrasting

confidence: 83%

Section: Nonbonded Interactions Involving a Divalent Sulfur Atommentioning

confidence: 99%

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Chalcogen Bonds in Protein Architecture

Iwaoka

2015

Challenges and Advances in Computational Chemistry and Physics

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“…On the other hand, the two carbonyl groups in thioanhydride 6 are in the same direction, with an interplanar angle [O(11)–C(11)–C(21)–O(21) of 30.5(1)° and the distance between the two carbonyl oxygen atoms [O(11)---O(21)] is only 2.761(2) Å, which suggests an O---O intramolecular nonbonding interaction. The alignment of O(22)–S(11)–C(11) is nearly linear: 173.4 (7)° [ 7 , 9 ].…”

Section: Resultsmentioning

confidence: 99%

Diaroyl Tellurides: Synthesis, Structure and NBO Analysis of (2-MeOC6H4CO)2Te – Comparison with Its Sulfur and Selenium Isologues. The First Observation of [MgBr][R(C=Te)O] Salts

et al. 2009

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A series of aromatic diacyl tellurides were prepared in moderate to good yields by the reactions of sodium or potassium arenecarbotelluroates with acyl chlorides in acetonitrile. X-ray structure analyses and theoretical calculations of 2-methoxybenzoic anhydride and bis(2-methoxybenzoyl) sulfide, selenide and telluride were carried out. The two 2-MeOC6H4CO moieties of bis(2-methoxybenzoyl) telluride are nearly planar and the two methoxy oxygen atoms intramolecularly coordinate to the central tellurium atom from both side of C(11)-Te(11)-C(22) plane. In contrast, the oxygen and sulfur isologues (2-MeOC6H4CO)2E (E = O, S), show that one of the two methoxy oxygen atoms contacts with the oxygen atom of the carbonyl group connected to the same benzene ring. The structure of di(2-methoxybenzoyl) selenide which was obtained by MO calculation resembles that of tellurium isologues rather than the corresponding oxygen and sulfur isologues. The reactions of di(aroyl) tellurides with Grignard reagents lead to the formation of tellurocarboxylato magnesium complexes [MgBr][R(C=Te)O].

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“…A kén-és oxigénatomok közötti vonzó kölcsönhatások kialakulásának szerkezeti feltételeit röntgen-és elektrondiffrakciós vizsgálatok eredményeinek elemzése alapján tapasztalati szabályokba foglaltuk össze. 61 A kölcsönhatásban lévõ atomok távolságát a kovalens és hipervalens kötések hosszával, valamint a van der Waals távolsággal együtt tárgyaltuk. Különösen érdekes tapasztalatokat eredményezett kén-oxigén nemkötõ kölcsönhatások és a hipervalens kötések tartományának összevetése, mert ezek átfedésben vannak egymással.…”

Section: Kén-oxigén Kölcsönhatásokunclassified