Crystal engineering of molecular networks. Hydrogen bonding driven two-dimensional assemblies of tetrapyridylporphyrin with benzene tri- and tetra-carboxylic acids

CrystEngComm ◽  
2009 ◽  
Vol 11 (7) ◽  
pp. 1217 ◽  
Author(s):  
Rajesh Koner ◽  
Israel Goldberg
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acids ◽  
Crystal Engineering ◽  
Molecular Networks ◽  
Two Dimensional

C-H…N≡C Hydrogen Bonding in Cyanobenzene-Ethylenedithio-Tetrathiafulvalene Compounds

CrystEngComm ◽  
2022 ◽  
Author(s):  
Sandra Rabaça ◽  
Isabel Cordeiro Santos ◽  
Gonçalo Lopes ◽  
Vasco Pires Silva da Gama ◽  
Luis Filipe F. Veiros ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Two Dimensional ◽  
Conducting Materials ◽  
New Type

The importance of the C-H…N≡C interactions in the crystal engineering of conducting materials was recently put into evidence in a new type of two-dimensional conducting materials with composition (5-CNB-EDT-TTF)4A with...

Crystal Engineering Using Tris-phenols. Cross-Linked, Pairwise-Interwoven Two-Dimensional Nets in the 2:1 Adduct of 1,1,1-Tris(4-hydroxyphenyl)ethane with 1,2-Diaminoethane

1998 ◽  
Vol 54 (3) ◽  
pp. 330-338 ◽  
Author(s):  
G. Ferguson ◽  
C. Glidewell ◽  
R. M. Gregson ◽  
P. R. Meehan
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Three Dimensional ◽  
Two Dimensional ◽  
Dimensional Array ◽  
Site Occupation

In 1,1,1-tris(4-hydroxyphenyl)ethane–1,2-diaminoethane (2/1), [CH3C(C6H4OH)3]2.H2NCH2CH2NH2 (1), triclinic, P1¯, with Z = 2, a = 10.9430 (12), b = 11.1075 (12), c = 15.249 (2) Å, α = 98.672 (15), β = 96.312 (10), γ = 98.377 (13)°, the tris-phenol units form continuous two-dimensional nets, built from pseudo-hexagonal R^4_4(38) rings, interwoven pairs of which are cross-linked by the 1,2-diaminoethane units. Each tris-phenol unit acts as a triple donor, forming two O—H...O and one O—H...N hydrogen bonds, and as a double acceptor in two O—H...O hydrogen bonds: the diamine unit, in which the CH2 groups are disordered over two sets of sites with site-occupation factors of 0.740 (5) and 0.260 (5), respectively, acts as a double acceptor only and the N—H bonds play no role in the hydrogen bonding. The O...O distances in the O—H...O hydrogen bonds are 2.642 (2), 2.690 (2), 2.810 (2) and 2.835 (2) Å, and the two independent O...N distances are both 2.665 (3) Å. Adjacent bilayers are connected into a continuous three-dimensional array by C—H...O hydrogen bonds, all having a C...O distance of 3.468 (4) Å.

“Crystal Engineering” with Two-Dimensional Hydrogen Bonding Networks

1999 ◽  
pp. 133-144
Author(s):  
J. A. Swift ◽  
A. M. Pivovar ◽  
A. M. Reynolds ◽  
C. C. Evans ◽  
V. A. Russell ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Two Dimensional ◽  
Hydrogen Bonding Networks

scholarly journals Covalent Assistance to Supramolecular Synthesis

2014 ◽  
Vol 70 (a1) ◽  
pp. C987-C987
Author(s):  
Andreas Lemmerer ◽  
Lee Madeley ◽  
Mark Smith
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Carboxylic Acids ◽  
Organic Synthesis ◽  
Crystal Engineering ◽  
Functional Group ◽  
Isonicotinic Acid ◽  
Acid Hydrazide ◽  
Molecular Complexes ◽  
Isonicotinic Acid Hydrazide

The similarity of crystal engineering to organic synthesis has been noted by Desiraju and many concepts and strategies have been successfully transferred. We aim to combine the two fields of research into one new concept called "Covalent Assistance to Supramolecular Synthesis". The supramolecular reagent isonicotinic acid hydrazide (isoniazid) is a promising molecule in the supramolecular synthesis of multi-component molecular complexes (Lemmerer at al., 2010). Due to the covalent reaction of the carbohydrazide functional group with simple ketones and aldehydes, the hydrogen bonding functionality of isoniazid can be modified, where two of the hydrogen bond donors are replaced with hydrogen bonding "inert" hydrocarbons (Lemmerer et al., 2011). The "modifiers" bonded to the isoniazid then give a measure of control of the outcome of the supramolecular synthesis with various carboxylic acids depending on the identity and steric size of the modifier used. The steric size itself can be used to shield or to "mask" the remaining hydrogen bonding functionality of isoniazid such that common homomeric and heteromeric interactions are prevented from taking place.

Template mediated crystal engineering

1994 ◽  
Vol 52 ◽  
pp. 480-481
Author(s):  
Brigid R. Heywood ◽  
S. Champ
Keyword(s):  
Crystal Engineering ◽  
Electrostatic Interactions ◽  
Alkyl Chain ◽  
Crystallographic Axis ◽  
Two Dimensional ◽  
Engineering Process ◽  
Solution Interface ◽  
Extensive Program ◽  
Geometric Homology ◽  
Long Alkyl Chain

Recent work on the crystallisation of inorganic crystals under compressed monomolecular surfactant films has shown that two dimensional templates can be used to promote the oriented nucleation of solids. When a suitable long alkyl chain surfactant is cast on the crystallisation media a monodispersied population of crystals forms exclusively at the monolayer/solution interface. Each crystal is aligned with a specific crystallographic axis perpendicular to the plane of the monolayer suggesting that nucleation is facilitated by recognition events between the nascent inorganic solid and the organic template.For example, monolayers of the long alkyl chain surfactant, stearic acid will promote the oriented nucleation of the calcium carbonate polymorph, calcite, on the (100) face, whereas compressed monolayers of n-eicosyl sulphate will induce calcite nucleation on the (001) face, (Figure 1 & 2). An extensive program of research has confirmed the general principle that molecular recognition events at the interface (including electrostatic interactions, geometric homology, stereochemical complementarity) can be used to promote the crystal engineering process.

Concomitant polymorphs of 1,3-bis(3-fluorophenyl)urea

2016 ◽  
Vol 72 (9) ◽  
pp. 692-696 ◽  
Author(s):  
Christina A. Capacci-Daniel ◽  
Jeffery A. Bertke ◽  
Shoaleh Dehghan ◽  
Rupa Hiremath-Darji ◽  
Jennifer A. Swift
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Structural Motif ◽  
Parallel Orientation ◽  
One Dimensional ◽  
Monoclinic Form ◽  
Engineering Studies ◽  
Hydrogen Bonded

Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluorophenyl)urea, C13H10F2N2O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many diphenylureas. In the orthorhombic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted diphenylureas.

Sign in / Sign up

Export Citation Format

Share Document