C–H⋯S interaction exhibits all the characteristics of conventional hydrogen bonds

2020 ◽  
Vol 22 (31) ◽  
pp. 17482-17493 ◽  
Author(s):  
Sanat Ghosh ◽  
Pragya Chopra ◽  
Sanjay Wategaonkar
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor

This is a tale of a pair of a hydrogen bond donor and acceptor, namely the CH donor and sulphur acceptor, neither of which is a conventional hydrogen bond participant.

scholarly journals Crystallographic study of self-organization in the solid state including quasi-aromatic pseudo-ring stacking interactions in 1-benzoyl-3-(3,4-dimethoxyphenyl)thiourea and 1-benzoyl-3-(2-hydroxypropyl)thiourea

2017 ◽  
Vol 73 (1) ◽  
pp. 52-56 ◽  
Author(s):  
Andrzej Okuniewski ◽  
Damian Rosiak ◽  
Jarosław Chojnacki ◽  
Barbara Becker
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Strong Hydrogen Bond ◽  
Compound I ◽  
Hydrogen Bond Donor ◽  
Hydrogen Bond Formation ◽  
Oh Groups ◽  
Space Group ◽  
Donor And Acceptor ◽  
Phenyl Rings

1-Benzoylthioureas contain both carbonyl and thiocarbonyl functional groups and are of interest for their biological activity, metal coordination ability and involvement in hydrogen-bond formation. Two novel 1-benzoylthiourea derivatives, namely 1-benzoyl-3-(3,4-dimethoxyphenyl)thiourea, C16H16N2O3S, (I), and 1-benzoyl-3-(2-hydroxypropyl)thiourea, C11H14N2O2S, (II), have been synthesized and characterized. Compound (I) crystallizes in the space group P\overline{1}, while (II) crystallizes in the space group P21/c. In both structures, intramolecular N—H...O hydrogen bonding is present. The resulting six-membered pseudo-rings are quasi-aromatic and, in each case, interact with phenyl rings via stacking-type interactions. C—H...O, C—H...S and C—H...π interactions are also present. In (I), there is one molecule in the asymmetric unit. Pairs of molecules are connected via two intermolecular N—H...S hydrogen bonds, forming centrosymmetric dimers. In (II), there are two symmetry-independent molecules that differ mainly in the relative orientations of the phenyl rings with respect to the thiourea cores. Additional strong hydrogen-bond donor and acceptor –OH groups participate in the formation of intermolecular N—H...O and O—H...S hydrogen bonds that join molecules into chains extending in the [001] direction.

scholarly journals When are two hydrogen bonds better than one? Accurate first-principles models explain the balance of hydrogen bond donors and acceptors found in proteins

2021 ◽  
Author(s):  
Vyshnavi Vennelakanti ◽  
Helena W. Qi ◽  
Rimsha Mehmood ◽  
Heather J. Kulik
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
High Resolution ◽  
Hydrogen Bonds ◽  
First Principles ◽  
Crystal Structure Analysis ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor ◽  
Stabilizing Effect ◽  
Better Than

Correlated wavefunction theory predicts and high-resolution crystal structure analysis confirms the important, stabilizing effect of simultaneous hydrogen bond donor and acceptor interactions in proteins.

6,9-Dibromo-2a,10b-diphenyl-2a,5,10,10b-tetrahydro-2H,3H-2,3,4a,10a-tetraazabenzo[g]cyclopenta[cd]azulene-1,4-dione monohydrate

2006 ◽  
Vol 62 (5) ◽  
pp. o1754-o1755
Author(s):  
Neng-Fang She ◽  
Sheng-Li Hu ◽  
Hui-Zhen Guo ◽  
An-Xin Wu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Supramolecular Structure ◽  
Hydrogen Bond Donor ◽  
Hydrogen Bond Acceptor ◽  
Compound C ◽  
Bifurcated Hydrogen Bond

The title compound, C24H18Br2N4O2·H2O, forms a supramolecular structure via N—H...O, O—H...O and C—H...O hydrogen bonds. In the crystal structure, the water molecule serves as a bifurcated hydrogen-bond acceptor and as a hydrogen-bond donor.

scholarly journals Machine learning models for hydrogen bond donor and acceptor strengths using large and diverse training data generated by first-principles interaction free energies

2019 ◽  
Vol 11 (1) ◽  
Author(s):  
Christoph A. Bauer ◽  
Gisbert Schneider ◽  
Andreas H. Göller
Keyword(s):  
Machine Learning ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Training Data ◽  
Free Energies ◽  
Hydrogen Bond Donor ◽  
Chemical Application ◽  
Hydrogen Bond Acceptor ◽  
Donor And Acceptor ◽  
Target Values

Abstract We present machine learning (ML) models for hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) strengths. Quantum chemical (QC) free energies in solution for 1:1 hydrogen-bonded complex formation to the reference molecules 4-fluorophenol and acetone serve as our target values. Our acceptor and donor databases are the largest on record with 4426 and 1036 data points, respectively. After scanning over radial atomic descriptors and ML methods, our final trained HBA and HBD ML models achieve RMSEs of 3.8 kJ mol−1 (acceptors), and 2.3 kJ mol−1 (donors) on experimental test sets, respectively. This performance is comparable with previous models that are trained on experimental hydrogen bonding free energies, indicating that molecular QC data can serve as substitute for experiment. The potential ramifications thereof could lead to a full replacement of wetlab chemistry for HBA/HBD strength determination by QC. As a possible chemical application of our ML models, we highlight our predicted HBA and HBD strengths as possible descriptors in two case studies on trends in intramolecular hydrogen bonding.

scholarly journals Electronic origin of the dependence of hydrogen bond strengths on nearest-neighbor and next-nearest-neighbor hydrogen bonds in polyhedral water clusters (H2O)n, n = 8, 20 and 24

2016 ◽  
Vol 18 (29) ◽  
pp. 19746-19756 ◽  
Author(s):  
Suehiro Iwata ◽  
Dai Akase ◽  
Misako Aida ◽  
Sotiris S. Xantheas
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Nearest Neighbor ◽  
Water Clusters ◽  
Hydrogen Donor ◽  
Donor And Acceptor ◽  
Bond Strengths

Comparison of the sum of the characteristic factors for some of the typical hydrogen donor and acceptor pairs with the CT term/kJ mol−1 (the upper value) and the O⋯O distance/in cubic (H2O)8.

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

The hydrogen bond donor and acceptor ability of thioformic acid

2011 ◽  
Vol 22 (5) ◽  
pp. 1015-1030 ◽  
Author(s):  
Damanjit Kaur ◽  
Ritika Sharma ◽  
Darpandeep Aulakh
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor

Secondary Interactions in Gold(I) Complexes with Thione Ligands, 3. Three Ionic Dimesylamides [1, 2]

2004 ◽  
Vol 59 (11-12) ◽  
pp. 1429-1437 ◽  
Author(s):  
Friedrichsa Friedrichsa ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Layer Structure ◽  
Chain Structure ◽  
Hydrogen Bond Donor ◽  
Weak Hydrogen Bonds ◽  
Ribbon Structure ◽  
A Chain ◽  
Aurophilic Interactions ◽  
Short Contacts

Three structures of the form bis(thione)gold(I) di(methanesulfonyl)amide [thione = imidazolidine- 2-thione, 1; 1-methyl-imidazolidine-2-thione, 2; thiazolidine-2-thione, 3] were determined; all crystallize with one formula unit in the asymmetric unit. Each N-H hydrogen bond donor forms one classical two-centre hydrogen bond with an anion acceptor. Compound 1 thereby forms a complex layer structure with a layer thickness of 10.17 Å ; the packing may be analysed in terms of thinner subunit layers consisting of interlinked, hydrogen-bonded chains and rings. Compound 2 forms a chain structure consisting of a series of “hairpin bends”, a common feature in the gold complexes of 1-alkyl-imidazolidine-2-thiones. Compound 3 forms a corrugated ribbon structure in which the central region consists of parallel S-Au-S axes linked by aurophilic interactions; the anions exercise a “clamping” function by forming hydrogen bonds at the periphery of the ribbons. Further short contacts can be classed as weak hydrogen bonds C-H ··· X, with X = N, O, S or Au.

Selective encapsulation and extraction of hydrogenphosphate by a hydrogen bond donor tripodal receptor

CrystEngComm ◽  
2020 ◽  
Vol 22 (37) ◽  
pp. 6152-6160
Author(s):  
Sandeep Kumar Dey ◽  
Archana ◽  
Sybil Pereira ◽  
Sarvesh S. Harmalkar ◽  
Shashank N. Mhaldar ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Hydrogen Bond Donor ◽  
Tripodal Receptor ◽  
Multiple Hydrogen Bonds

Intramolecular N–H⋯OC hydrogen bonding between the inner amide groups dictates the receptor–anion complementarity in a tripodal receptor towards selective encapsulation of hydrogenphosphate in the outer urea cavity by multiple hydrogen bonds.

Synthesis and preliminary bioactivity evaluation of new pregnane brassinosteroid-like compounds

2005 ◽  
Vol 83 (8) ◽  
pp. 1084-1092 ◽  
Author(s):  
Daniel G Rivera ◽  
Francisco Coll
Keyword(s):  
Hydrogen Bond ◽  
Plant Growth ◽  
Hypocotyl Elongation ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor ◽  
Plant Growth Promoting ◽  
Plant Growth Promoting Activity ◽  
Growth Promoting ◽  
Cotyledon Expansion

Seven new pregnane compounds bearing some representative A- and B-ring brassinosteroid functions, as well as hydrogen bond donor and acceptor ones on the D ring, were efficiently synthesized. The obtained compounds did not show remarkable plant growth-promoting activity in the radish hypocotyl elongation and cotyledon expansion bioassays, however, introducing oxygen and amino functions on the D ring led to an enhancement of the bioactivity. The 16β-functionalized pregnane brassinosteroid-like compounds were slightly more active than the 16α-functionalized ones.Key words: steroids, brassinosteroids, pregnane analogues.

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