scholarly journals ‘Frustrated’ hydrogen bond mediated amphiphile self-assembly – a solid state study

CrystEngComm ◽  
2016 ◽  
Vol 18 (37) ◽  
pp. 7021-7028 ◽  
Author(s):  
Laura R. Blackholly ◽  
Helena J. Shepherd ◽  
Jennifer R. Hiscock
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Self Assembly ◽  
Hydrogen Bond Donor ◽  
System P ◽  
State Study ◽  
Counter Cation ◽  
Self Assembled ◽  
Hydrogen Bonded

The effects of hydrogen bond donor acidity and counter cation within a ‘frustrated’ self-assembled, hydrogen bonded system.

N-Tosyl-L-proline benzene hemisolvate: a rare example of a hydrogen-bonded carboxylic acid dimer with symmetrically disordered H atoms

2019 ◽  
Vol 75 (9) ◽  
pp. 1228-1233
Author(s):  
Joanna Wojnarska ◽  
Katarzyna Ostrowska ◽  
Marlena Gryl ◽  
Katarzyna Marta Stadnicka
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Self Assembly ◽  
Acid Group ◽  
Benzene Molecule ◽  
Noncovalent Interaction ◽  
Hydrogen Bond Donor ◽  
Donor And Acceptor ◽  
Carboxylic Acid Dimer ◽  
Hydrogen Bonded

The carboxylic acid group is an example of a functional group which possess a good hydrogen-bond donor (–OH) and acceptor (C=O). For this reason, carboxylic acids have a tendency to self-assembly by the formation of hydrogen bonds between the donor and acceptor sites. We present here the crystal structure of N-tosyl-L-proline (TPOH) benzene hemisolvate {systematic name: (2S)-1-[(4-methylbenzene)sulfonyl]pyrrolidine-2-carboxylic acid benzene hemisolvate}, C12H15NO4S·0.5C6H6, (I), in which a cyclic R 2 2(8) hydrogen-bonded carboxylic acid dimer with a strong O—(1 \over 2H)...(1 \over 2H)—O hydrogen bond is observed. The compound was characterized by single-crystal X-ray diffraction and NMR spectroscopy, and crystallizes in the space group I2 with half a benzene molecule and one TPOH molecule in the asymmetric unit. The H atom of the carboxyl OH group is disordered over a twofold axis. An analysis of the intermolecular interactions using the noncovalent interaction (NCI) index showed that the TPOH molecules form dimers due to the strong O—(1 \over 2H)...(1 \over 2H)—O hydrogen bond, while the packing of the benzene solvent molecules is governed by weak dispersive interactions. A search of the Cambridge Structural Database revealed that the disordered dimeric motif observed in (I) was found previously only in six crystal structures.

Rage Against Conformity: Ruthenium(ɪɪ) Bisterpyridine Complexes Respond to Crystal Engineering Instructions with Whelming Results

2017 ◽  
Vol 70 (5) ◽  
pp. 529 ◽  
Author(s):  
Hasti Iranmanesh ◽  
Kasun S. A. Arachchige ◽  
William A. Donald ◽  
Niamh Kyriacou ◽  
Chao Shen ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Solid State ◽  
Single Crystal ◽  
Crystal Engineering ◽  
Intermolecular Hydrogen Bonding ◽  
Hydrogen Bond Donor ◽  
One Dimensional ◽  
X Ray ◽  
Hydrogen Bonded

Four heteroleptic ruthenium(ii) complexes of 4′-functionalised 2,2′:6′,2′′-terpyridine are reported, along with their solid-state single-crystal X-ray structures. The complexes feature complementary hydrogen-bond donor (phenol) and acceptor (pyridyl) groups designed to assemble into one-dimensional polymers. In one example, the system obeys the programmed instructions to form a one-dimensional, self-complementary hydrogen-bonded polymer. In one other example, a water-bridged hydrogen-bonded polymer is formed. In the remaining two structures, aryl–aryl interactions dominate the intermolecular interactions, and outweigh the contribution of intermolecular hydrogen bonding.

scholarly journals Fluorination as a route towards unlocking the hydrogen bond donor ability of phenolic compounds in self-assembled monolayers

CrystEngComm ◽  
2020 ◽  
Vol 22 (14) ◽  
pp. 2425-2428
Author(s):  
Harry Pinfold ◽  
Graham Pattison ◽  
Giovanni Costantini
Keyword(s):  
Hydrogen Bond ◽  
Phenolic Compounds ◽  
Building Block ◽  
Self Assembled Monolayers ◽  
Hydrogen Bond Donor ◽  
Assembled Monolayers ◽  
Donor Ability ◽  
Self Assembled ◽  
Effective Hydrogen

Fluorination turns a prototypical diphenol into an effective hydrogen-bond-donating building block for the formation of 2D phenol–pyridine cocrystals.

Infrared spectroscopic characterization of hydrogen-bonded propylene oxide − ethanol and propylene oxide − 2-fluoroethanol complexes isolated in solid neon matrices

2013 ◽  
Vol 91 (12) ◽  
pp. 1292-1302 ◽  
Author(s):  
Osama Y. Ali ◽  
Elyse Jewer ◽  
Travis D. Fridgen
Keyword(s):  
Hydrogen Bond ◽  
Propylene Oxide ◽  
Spectroscopic Characterization ◽  
Hydrogen Bond Donor ◽  
Hydrogen Bond Acceptor ◽  
Reduced Frequency ◽  
Enthalpy Of Proton Transfer ◽  
The Difference ◽  
Bonded Complexes ◽  
Hydrogen Bonded

The infrared absorption spectra of hydrogen-bonded complexes of propylene oxide with either ethanol or 2-fluoroethanol have been recorded in neon matrices. Mixtures of propylene oxide and ethanol or propylene oxide and 2-fluoroethanol vapors were mixed with an excess of neon gas and deposited onto a KBr substrate at 4.2 K. The results indicate that hydrogen-bonded complexes were formed with propylene oxide as the hydrogen bond acceptor and either ethanol or 2-fluoroethanol as the hydrogen bond donors. The features assigned to the O−H stretch were red-shifted by 175 and 193 cm−1 for the ethanol- and 2-fluoroethanol-containing complexes, respectively. The difference in red shifts can be accounted for due to the greater acidity of 2-fluroethanol. Deuterium isotope experiments were conducted to help confirm the assignment of the O–H stretch for the complexes. As well, structures and infrared spectra were calculated using B3LYP/6-311++G(2d,2p) calculations and were used to compare with the experimental spectra. A “scaling equation” rather than a scaling factor was used and is shown to greatly increase the utility of the calculations when comparing with experimental spectra. An examination of the O–H stretching red shifts for many hydrogen-bound complexes reveals a relationship between the shift and the difference between the acidity of the hydrogen bond donor and the basicity of the hydrogen bond acceptor (the enthalpy of proton transfer). Both hydrogen-bonded complexes and proton-bound complexes appear to have a maximum in the reduced frequency value that corresponds to complexes where the hydrogen/proton are equally shared between the two bases.

The heterobifunctional ligand 5-[4-(1,2,4-triazol-4-yl)phenyl]-1H-tetrazole and its role in the construction of a CdIImetal–organic chain structure

2012 ◽  
Vol 68 (10) ◽  
pp. m291-m294
Author(s):  
Andrey B. Lysenko
Keyword(s):  
Hydrogen Bond ◽  
Three Dimensional ◽  
Organic Ligand ◽  
Chain Structure ◽  
Polar Space ◽  
Hydrogen Bond Donor ◽  
Donor Acceptor ◽  
A Chain ◽  
Water Ligands ◽  
Hydrogen Bonded

5-[4-(1,2,4-Triazol-4-yl)phenyl]-1H-tetrazole, C9H7N7, (I), an asymmetric heterobifunctional organic ligand containing triazole (tr) and tetrazole (tz) termini linked directly through a 1,4-phenylene spacer, crystallizes in the polar space groupPc. The heterocyclic functions, serving as single hydrogen-bond donor (tz) or acceptor (tr) units, afford hydrogen-bonded zigzag chains with no crystallographic centre of inversion. In the structure ofcatena-poly[[diaquacadmium(II)]bis{μ2-5-[4-(1,2,4-triazol-4-yl)phenyl]tetrazol-1-ido-κ2N1:N1′}], [Cd(C9H6N7)2(H2O)2]n, (II), the CdIIdication resides on a centre of inversion in an octahedral {N4O2} environment. In the equatorial plane, the CdIIpolyhedron is built up from four N atoms of two kinds, namely oftrans-coordinating tr and tz fragments [Cd—N = 2.2926 (17) and 2.3603 (18) Å], and the coordinating aqua ligands occupy the two apical sites. The metal centres are separated at a distance of 11.1006 (7) Å by means of the double-bridging tetrazolate anion,L−, forming a chain structure. The water ligands and tz fragments interact with one another, like a double hydrogen-bond donor–acceptor synthon, leading to a hydrogen-bonded three-dimensional array.

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