The Impact of the Length of Alkyl Chain on the Behavior of Benzyl Alcohol Homologous. The Interplay Between Dispersive and Hydrogen Bond Interactions

2021 ◽  
Author(s):  
Natalia Soszka ◽  
Barbara Hachuła ◽  
Magdalena Tarnacka ◽  
Ewa Ozimina-Kamińska ◽  
Joanna Grelska ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Benzyl Alcohol ◽  
Benzene Ring ◽  
Alkyl Chain ◽  
The Self ◽  
Hydrogen Bond Interactions ◽  
Self Assembling ◽  
The Impact

In this work, we examined the effect of length of alkyl chain attached to the benzene ring on the self-assembling phenomena for the series of phenol alcohol (PhA) derivatives, from...

scholarly journals Crystal structure of 4-{[(1H-1,2,4-triazol-1-yl)methyl]sulfanyl}phenol

2014 ◽  
Vol 70 (10) ◽  
pp. o1106-o1106
Author(s):  
Yong-Le Zhang ◽  
Chuang Zhang ◽  
Wei Guo ◽  
Jing Wang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Three Dimensional ◽  
Triazole Ring ◽  
Hydrogen Bond Interactions ◽  
Compound C ◽  
Dimensional Network

In the title compound, C9H9N3OS, the plane of the benzene ring forms a dihedral angle of 33.40 (5)° with that of the triazole group. In the crystal, molecules are linked by O—H...N hydrogen bonds involving the phenol –OH group and one of the unsubstituted N atoms of the triazole ring, resulting in chains along [010]. These chains are further extended into a layer parallel to (001) by weak C—H...N hydrogen-bond interactions. Aromatic π–π stacking [centroid–centroid separation = 3.556 (1) Å] between the triazole rings links the layers into a three-dimensional network.

3-Anilinoisobenzofuran-1(3H)-one

2006 ◽  
Vol 62 (7) ◽  
pp. o2943-o2944 ◽  
Author(s):  
Mustafa Odabaşoğlu ◽  
Orhan Büyükgüngör
Keyword(s):  
Hydrogen Bond ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Hydrogen Bond Interactions ◽  
Compound C

Crystals of the title compound, C14H11NO2, are stabilized by an intermolecular N—H...O hydrogen bond and a weak π–π interaction. N—H...O hydrogen-bond interactions generate C(6) chains. The phthalide section of the molecule is planar and the dihedral angle between the phthalide group and the benzene ring is 78.43 (5)°.

scholarly journals Contrasting the Conformational Effects of α-O-GalNAc and α-O-Man Glycan Protein Modifications and their Impact on the Mucin-Like Region of alpha-Dystroglycan

Glycobiology ◽  
2020 ◽  
Author(s):  
Andrew Borgert ◽  
B Lachele Foley ◽  
David Live
Keyword(s):  
Mechanical Properties ◽  
Molecular Dynamics ◽  
Hydrogen Bond ◽  
Solution Nmr ◽  
Threonine Residue ◽  
Hydrogen Bond Interactions ◽  
Conformational Effects ◽  
Molecular Dynamics Calculations ◽  
Alpha Dystroglycan ◽  
The Impact

Abstract We have carried out a comparative study of the conformational impact of modifications to threonine residues of either α-O-Man or α-O-GalNAc in the context of a sequence from the mucin-like region of α-dystroglycan. Both such modifications can coexist in this domain of the glycoprotein. Solution NMR experiments and molecular dynamics calculations were employed. Comparing the results for a unmodified peptide Ac- PPTTTTKKP-NH2 sequence from α-dystroglycan, and glycoconjugates with either modification on the Ts, we find that the impact of the α-O-Man modification on the peptide scaffold is quite limited, while that of the α-O-GalNAc is more profound. The results for the α-O-GalNAc glycoconjugate are consistent with what has been seen earlier in other systems. Further examination of the NMR-based structure and the MD results suggest a more extensive network of hydrogen bond interactions within the α-O-GalNAc-threonine residue than has been previously appreciated, which influence the properties of the protein backbone. The conformational effects are relevant to the mechanical properties of α-dystroglycan.

scholarly journals Crystal structure of 3-(3,4-dimethylanilino)-2-benzofuran-1(3H)-one

2015 ◽  
Vol 71 (6) ◽  
pp. o413-o413
Author(s):  
Muhammad Salim ◽  
Muhammad Nawaz Tahir ◽  
Muhammad Shahid ◽  
Munawar Ali Munawar
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Benzene Ring ◽  
Title Compound ◽  
Methyl Groups ◽  
Stacking Interactions ◽  
Hydrogen Bond Interactions ◽  
Compound C ◽  
Centroid Distance ◽  
Benzene Rings

In the title compound, C16H15NO2, the 2-benzofuran-1(3H)-one and 3,4-dimethylaniline fragments are oriented with a dihedral angle of 89.12 (5)°. N—H...O hydrogen-bond interactions join molecules intoC(6) chains propagating along theaaxis. In addition, there are π–π stacking interactions between the 2-benzofuranone benzene rings [centroid–centroid distance = 3.7870 (13) Å] and C—H...π interactions between one of the methyl groups and the 3,4-dimethylaniline benzene ring.

scholarly journals Supramolecular polymerisation in water; elucidating the role of hydrophobic and hydrogen-bond interactions

Soft Matter ◽  
2016 ◽  
Vol 12 (11) ◽  
pp. 2887-2893 ◽  
Author(s):  
Christianus M. A. Leenders ◽  
Matthew B. Baker ◽  
Imke A. B. Pijpers ◽  
René P. M. Lafleur ◽  
Lorenzo Albertazzi ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Self Assembly ◽  
The Self ◽  
Hydrogen Bond Interactions

The self-assembly of a family of benzene-1,3,5-tricarboxamides (BTAs) in water is studied systematically to elucidate the role of hydrophobic and hydrogen-bond interactions.

3,5-Difluorobenzohydrazide

2007 ◽  
Vol 63 (3) ◽  
pp. o1176-o1177 ◽  
Author(s):  
Ghulam Qadeer ◽  
Nasim Hasan Rama ◽  
Muhammad Zareef ◽  
Wai-Yeung Wong
Keyword(s):  
Hydrogen Bond ◽  
Benzene Ring ◽  
Title Compound ◽  
Heterocyclic Compounds ◽  
Crystal Packing ◽  
Biologically Active ◽  
Hydrogen Bond Interactions ◽  
Compound C ◽  
Important Intermediate

The title compound, C7H6F2N2O, is an important intermediate for the synthesis of biologically active heterocyclic compounds. The hydrazide group is nearly coplanar with the benzene ring. The crystal packing is stabilized by N—H...O and N—H...N hydrogen-bond interactions.

scholarly journals Cyclodextrin-based facial amphiphiles: assessing the impact of the hydrophilic–lipophilic balance in the self-assembly, DNA complexation and gene delivery capabilities

2016 ◽  
Vol 14 (42) ◽  
pp. 10037-10049 ◽  
Author(s):  
Iris Pflueger ◽  
Coralie Charrat ◽  
Carmen Ortiz Mellet ◽  
José M. García Fernández ◽  
Christophe Di Giorgio ◽  
...  
Keyword(s):  
Gene Delivery ◽  
Self Assembly ◽  
The Self ◽  
Self Assembling ◽  
Hydrophilic Lipophilic Balance ◽  
The Impact

Precise tailoring of cationic and lipophilic domains of cyclodextrin-based amphiphiles permits the control of their self-assembling and gene delivery capabilities.

Four oxoindole-linked α-alkoxy-β-amino acid derivatives

2015 ◽  
Vol 71 (4) ◽  
pp. 322-329 ◽  
Author(s):  
Krishnan Ravikumar ◽  
Balasubramanian Sridhar ◽  
Jagadeesh Babu Nanubolu ◽  
Tamilselvan Rajasekaran ◽  
Basi Venkata Subba Reddy
Keyword(s):  
Hydrogen Bond ◽  
Amino Acid ◽  
Hydrogen Bonds ◽  
Benzyl Alcohol ◽  
Chemical Reaction ◽  
Amide Group ◽  
Amino Acid Derivatives ◽  
Relative Configuration ◽  
Extended Conformation ◽  
Hydrogen Bond Interactions

Four structures of oxoindolyl α-hydroxy-β-amino acid derivatives, namely, methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-methoxy-2-phenylacetate, C24H28N2O6, (I), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-ethoxy-2-phenylacetate, C25H30N2O6, (II), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-[(4-methoxybenzyl)oxy]-2-phenylacetate, C31H34N2O7, (III), and methyl 2-[(anthracen-9-yl)methoxy]-2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-phenylacetate, C38H36N2O6, (IV), have been determined. The diastereoselectivity of the chemical reaction involving α-diazoesters and isatin imines in the presence of benzyl alcohol is confirmed through the relative configuration of the two stereogenic centres. In esters (I) and (III), the amide group adopts ananticonformation, whereas the conformation issynin esters (II) and (IV). Nevertheless, the amide group forms intramolecular N—H...O hydrogen bonds with the ester and ether O atoms in all four structures. The ether-linked substituents are in the extended conformation in all four structures. Ester (II) is dominated by intermolecular N—H...O hydrogen-bond interactions. In contrast, the remaining three structures are sustained by C—H...O hydrogen-bond interactions.

Synthesis and self-assembly of photopolymerizable quarterthiophenes

2006 ◽  
Vol 937 ◽  
Author(s):  
Margarita Garcia ◽  
E.W. Meijer ◽  
Albertus Schenning
Keyword(s):  
Hydrogen Bond ◽  
Self Assembly ◽  
The Self ◽  
Side Chain ◽  
Side Chains ◽  
Aggregate Formation ◽  
Hydrogen Bond Interactions ◽  
Π Stacking ◽  
Self Assembled ◽  
Polymerizable Group

ABSTRACTA variety of α, α'-subtituted quaterthiophenes containing ester, amide and polymerizable side chains have been synthesized and fully characterized. The self-assembly properties of these oligothiophenes were studied as function of the side chain. Introduction of amide functionalities highly promotes the self-assembly via π-stacking and hydrogen bond interactions, while the lack of amides prevent aggregate formation. Initial experiments show that by introducing a sorbyl moiety as a polymerizable group it is possible to achieve covalent fixation of the oligothiophene units in the self-assembled state.

Competition and selectivity in supramolecular synthesis: structural landscape around 1-(pyridylmethyl)-2,2′-biimidazoles

2017 ◽  
Vol 203 ◽  
pp. 371-388 ◽  
Author(s):  
C. A. Gunawardana ◽  
J. Desper ◽  
A. S. Sinha ◽  
M. Ðaković ◽  
C. B. Aakeröy
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Proton Transfer ◽  
Halogen Bond ◽  
Crystal Formation ◽  
Halogen Bonds ◽  
Supramolecular Architectures ◽  
Hydrogen Bond Interactions ◽  
Structure Extension ◽  
The Impact

Three isomeric forms of 1-(pyridylmethyl)-2,2′-biimidazole, A1–A3, have been synthesized and subjected to systematic co-crystallizations with selected hydrogen- and halogen-bond donors in order to explore the impact of electrostatics and geometry on the resulting supramolecular architectures. The solid-state supramolecular behavior of A1–A3 is largely consistent in halogen-bonded co-crystals. Only two types of primary interactions, the N–H⋯N/N⋯H–N homomeric hydrogen-bond interactions responsible for the pairing of biimidazole moieties and the I⋯N(pyridine) halogen bonds responsible for the co-crystal formation and structure extension, are present in these systems. The co-crystallizations with hydrogen-bond donors (carboxylic acids), however, lead to multiple possible structural outcomes because of the presence of the biimidazole–acid N–H⋯OC/N⋯H–O heterosynthon that can compete with biimidazole–biimidazole N–H⋯N/N⋯H–N homosynthon. In addition, the somewhat unpredictable nature of proton transfer makes the hydrogen-bonded co-crystals structurally less consistent than their halogen-bonded counterparts.

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