Interaction topologies of the S⋯O chalcogen bond: the conformational equilibrium of the cyclohexanol⋯SO2 cluster

2021 ◽  
Author(s):  
Yan Jin ◽  
Rizalina T. Saragi ◽  
Marcos Juanes ◽  
Gang Feng ◽  
Alberto Lesarri
Keyword(s):  
Hydrogen Bonds ◽  
Conformational Equilibrium ◽  
Chalcogen Bond

The versatile SO2 engages simultaneously in a S⋯O chalcogen bond and C–H⋯O hydrogen bonds when interacting with cyclohexanol.

Role of the gauche effect and local 1,3-dipole–dipole interactions in stabilizing an unusual conformation of tartarodinitriles

2008 ◽  
Vol 64 (4) ◽  
pp. 497-503 ◽  
Author(s):  
Urszula Rychlewska ◽  
Natalia Waścinska ◽  
Beata Warżajtis ◽  
Jacek Gawroński
Keyword(s):  
Hydrogen Bonds ◽  
Tartaric Acid ◽  
Conformational Equilibrium ◽  
Carbon Chain ◽  
Dipolar Interactions ◽  
Nmr Studies ◽  
X Ray ◽  
Gauche Effect ◽  
Dipole Interactions

This paper reports the synthesis, X-ray and NMR investigations of chiral and meso dinitriles of tartaric acid (tartarodinitriles) and their O,O′-diacetyl and O,O′-dibenzoyl derivatives. While in chiral tartaric acid its esters and NH amides the four-atom carbon chain is overwhelmingly trans, it is gauche in chiral tartarodinitriles. Conversely, meso-tartaric acid, its esters and amides display a tendency for the gauche conformation, but meso-tartarodinitriles usually have the trans conformation. The NMR studies of tartarodinitriles reveal the presence of a conformational equilibrium in solution with a preference for those conformers found in crystals. The gauche conformation of meso-tartarodinitriles seems to be stabilized by local dipolar interactions, intramolecular C—H...O hydrogen bonds and by a tendency for maximization of the gauche effect, the latter effect also operating in chiral tartarodinitriles. Stabilization of the trans conformers of tartarodinitriles in the crystals seems to originate from specific intermolecular interactions.

scholarly journals Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

2015 ◽  
Vol 11 ◽  
pp. 2105-2116 ◽  
Author(s):  
Karina Mroczyńska ◽  
Małgorzata Kaczorowska ◽  
Erkki Kolehmainen ◽  
Ireneusz Grubecki ◽  
Marek Pietrzak ◽  
...  
Keyword(s):  
Experimental Data ◽  
Hydrogen Bonds ◽  
Systematic Approach ◽  
Conformational Equilibrium ◽  
Variable Temperature ◽  
Single Bond ◽  
Intramolecular Hydrogen Bonds ◽  
Title Molecule ◽  
Study Association ◽  
Intramolecular Hydrogen

The association of substituted benzoates and naphthyridine dianions was used to study the complexation of dibutyltriuret. The title molecule is the simplest molecule able to form two intramolecular hydrogen bonds. The naphthyridine salt was used to break two intramolecular hydrogen bonds at a time while with the use of substituted benzoates the systematic approach to study association was achieved. Both, titrations and variable temperature measurements shed the light on the importance of conformational equilibrium and its influence on association in solution. Moreover, the associates were observed by mass spectrometry. The DFT-based computations for complexes and single bond rotational barriers supports experimental data and helps understanding the properties of multiply hydrogen bonded complexes.

scholarly journals Binding motif of ebselen in solution: chalcogen and hydrogen bonds team up

2020 ◽  
Vol 44 (47) ◽  
pp. 20697-20703
Author(s):  
Andrea Daolio ◽  
Patrick Scilabra ◽  
Maria Enrica Di Pietro ◽  
Chiara Resnati ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Binding Motif ◽  
Supramolecular Synthon ◽  
Chalcogen Bond

Ebselen, a compound active against SARS-CoV-2, forms a bifurcated supramolecular synthon thanks to chalcogen bond and hydrogen bond cooperation.

Use of molecular overlap to predict intermolecular repulsion in N... H-O hydrogen bonds

1998 ◽  
Vol 95 (3) ◽  
pp. 525-537 ◽  
Author(s):  
I. NOBELI S. L. PRICE R. J. WHEATLEY
Keyword(s):  
Hydrogen Bonds

On symmetrical O-H-O hydrogen bonds

1964 ◽  
Vol 25 (5) ◽  
pp. 487-492 ◽  
Author(s):  
R.E. Rundle
Keyword(s):  
Hydrogen Bonds

CSLNs with assembled LIPID layer mediated by hydrogen bonds for saquinavir release

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
YC Kuo ◽  
CC Wang
Keyword(s):  
Hydrogen Bonds ◽  
Lipid Layer

A Crystallographic Study of Bis[S-benzyl-5-bromo-2-oxoindolin-3-ylidenemethanehydrazonthioate] Disulfide Solvated with Dimethylsulfoxide

2012 ◽  
Vol 9 (2) ◽  
pp. 87
Author(s):  
Mohd Abdul Fatah Abdul Manan ◽  
M. Ibrahim M. Tahir ◽  
Karen A. Crouse ◽  
Fiona N.-F. How ◽  
David J. Watkin
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Solvent Molecule ◽  
Site Occupancy ◽  
Unit Cell Parameters ◽  
Intermolecular Hydrogen Bonds ◽  
Triclinic Space Group ◽  
Cell Parameters ◽  
Crystallographic Study ◽  
Thiol Form

The crystal structure of the title compound has been determined. The compound crystallized in the triclinic space group P -1, Z = 2, V = 1839 .42( 18) A3 and unit cell parameters a= 11. 0460( 6) A, b = 13 .3180(7) A, c=13. 7321 (8) A, a = 80.659(3 )0, b = 69 .800(3 )0 and g = 77 .007 (2)0 with one disordered dimethylsulfoxide solvent molecule with the sulfur and oxygen atoms are distributed over two sites; S101/S102 [site occupancy factors: 0.6035/0.3965] and 0130/0131 [site occupancy factor 0.3965/0.6035]. The C22-S2 l and C 19-S20 bond distances of 1. 779(7) A and 1. 788(8) A indicate that both of the molecules are connected by the disulfide bond [S20-S21 2.055(2) A] in its thiol form. The crystal structure reveals that both of the 5-bromoisatin moieties are trans with respect to the [S21-S20 and CI 9-Nl 8] and [S20-S21 and C22-N23] bonds whereas the benzyl group from the dithiocarbazate are in the cis configuration with respect to [S21-S20 and C19-S44] and [S20-S21 and C22-S36] bonds. The crystal structure is further stabilized by intermolecular hydrogen bonds of N9-H35···O16 formed between the two molecules and N28-H281 ···O130, N28-H281 ···O131 and C4 l-H4 l l ···O 131 with the solvent molecule.

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