Sterically crowded hydrogen-bonded hexagonal network frameworks

2018 ◽  
Vol 2 (2) ◽  
pp. 338-346 ◽  
Author(s):  
Ichiro Hisaki ◽  
Nobuaki Ikenaka ◽  
Seiji Tsuzuki ◽  
Norimitsu Tohnai
Keyword(s):  
Substituent Effects ◽  
Molecular Assembly ◽  
Hexagonal Network ◽  
Hydrogen Bonded

TpMeandTpFwith substituents at theortho-positions of carboxy groups were synthesized and revealed substituent effects on molecular assembly.

A COMPARATIVE STUDY OF META/PARA SUBSTITUTION EFFECTS ON THE HYDROGEN-BONDED COMPLEX OF ANILINE-H2O: OBSERVATIONS FROM COMPUTATION

2011 ◽  
Vol 10 (05) ◽  
pp. 567-579 ◽  
Author(s):  
YING TAN ◽  
LIJUAN ZHU ◽  
XIUCHAN XIAO ◽  
SHUHUA HE ◽  
YANZHI GUO ◽  
...  
Keyword(s):  
Natural Bond Orbital ◽  
Substituent Effects ◽  
Binding Energies ◽  
Substitution Effects ◽  
Physical Origin ◽  
Aim Analysis ◽  
Position Effects ◽  
Meta Position ◽  
Text Interaction ◽  
Hydrogen Bonded

Compared with para-substitution, substituent effects ( R = NH 2, OH , CH 3, F , Cl , H , SiH 3, CHO , CN , NO 2) of meta-position effects on hydrogen-bonded complex of aniline with one water molecule are studied at B3LYP/6-311++G(d,p) level of theory. The differences in hydrogen bonding and some properties associated with the H -bond (such as bond length, vibrational frequency, binding energies, p K a values of aniline derivatives) are discussed between meta and para substitutions. Natural bond orbital (NBO) and atoms in molecules (AIM) analysis are applied to investigate the physical origin of the differences. The results show that the differences are mainly attributed to the variations in electron delocalization from amino group to phenyl ring (reflected by [Formula: see text] interaction) induced by substituents.

Pressure-induced molecular assembly of hydrogen-bonded polymers

2008 ◽  
Vol 46 (7) ◽  
pp. 743-750 ◽  
Author(s):  
Shingo Mutsuo ◽  
Kazuya Yamamoto ◽  
Tsutomu Furuzono ◽  
Tsuyoshi Kimura ◽  
Tsutomu Ono ◽  
...  
Keyword(s):  
Molecular Assembly ◽  
Hydrogen Bonded

A Step Towards a [2.2]Paracyclophane: A Single Crystal to Single Crystal Reaction Involving a Hydrogen-Bonded Molecular Assembly with Multiple Reaction Centres

2006 ◽  
Vol 59 (9) ◽  
pp. 613 ◽  
Author(s):  
Tomislav Friščić ◽  
Leonard R. MacGillivray
Keyword(s):  
Solid State ◽  
Single Crystal ◽  
Absorption Edge ◽  
Molecular Assembly ◽  
Solid State Synthesis ◽  
State Transformation ◽  
Molecular Assemblies ◽  
Solid State Transformation ◽  
Reaction Centres ◽  
Hydrogen Bonded

A single crystal to single crystal [2+2] photodimerization has been achieved within a molecular cocrystal composed of finite, hydrogen-bonded molecular assemblies using the absorption-edge irradiation technique. The cocrystal is composed of a resorcinol template and a diolefin reactant that reacts to form a non-symmetrical cyclobutane product. The product is an intermediate in a two-step solid-state synthesis of a [2.2]paracyclophane. The ability to conduct the reaction in a single crystal to single crystal fashion attests to the robustness of the hydrogen-bonded assemblies during the course of the solid-state transformation.

Stabilities in the gas phase of the hydrogen bonded complexes, YC6H4OH-X−, of substituted phenols, YC6E4OH, with the halide anions X− (Cl−, Br−, I−)

1990 ◽  
Vol 68 (11) ◽  
pp. 2070-2077 ◽  
Author(s):  
Gary J. C. Paul ◽  
Paul Kebarle
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Proton Transfer ◽  
Gas Phase ◽  
Equilibrium Constants ◽  
Substituent Effects ◽  
Closed Shell ◽  
Bond Energies ◽  
Substituted Phenols ◽  
Hydrogen Bonded

The equilibria, YPhOH + Br− = YPhOH-Br−, involving 26 differently substituted phenols, were determined with a pulsed high pressure mass spectrometer. The −ΔG0 evaluated from the equilibrium constants represent the hydrogen bond free energies in YPhOH-Br−. These data and data for X− = Cl− and I−, determined previously in this laboratory, are used to examine the substituent effects on the hydrogen bonding. It was found that the hydrogen bond energies in YPhOH-X− increase approximately linearly with the gas phase acidities of the phenols, YPhOH. This is in agreement with earlier observations that showed the bond energies in AH-B−, where AH were oxygen and nitrogen acids and B− closed shell anions, increase with increasing acidity of AH.A detailed analysis of the substituent effects, which is possible for YPhOH-X−, shows that the relationship with the acidity of AH can be divided into two parts. One is the increasing extent of actual proton transfer from AH on formation of the hydrogen bonded complex. Such proton transfer occurs in YPhOH-X− only for the series X− = Cl−. The second effect, which occurs for Cl− and is dominant for Br− and I−, is not directly related to the acidity of the phenols (or AH in general) but depends on a similarity of the substituent effects on the acidity and the stabilization of YPhOH-X− (or AH-B− in general). The dominant contribution to YPhOH-X− stabilization in this case is due to the field effects of the substituents, i.e., π delocalization plays only a small part. Therefore, the correlation with the acidity of YPhOH, where π delocalization is important, is not very close. Keywords: hydrogen bonding, substituent effects, ion–molecule equilibria, stability constants, thermochemistry.

Effect of Substituent Position on Molecular Assembly: Hydrogen-Bonded Arrangement of Aminobenzoates Adsorbed on Cu(110)

2009 ◽  
Vol 48 (8) ◽  
pp. 08JB16 ◽  
Author(s):  
Satoshi Katano ◽  
Masafumi Hori ◽  
Caroline Rabot ◽  
Yousoo Kim ◽  
Maki Kawai
Keyword(s):  
Molecular Assembly ◽  
Hydrogen Bonded

AC3-Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals

2015 ◽  
Vol 54 (10) ◽  
pp. 3008-3012 ◽  
Author(s):  
Ichiro Hisaki ◽  
Shoichi Nakagawa ◽  
Norimitsu Tohnai ◽  
Mikiji Miyata
Keyword(s):  
Molecular Crystals ◽  
Hexagonal Network ◽  
Hydrogen Bonded

AC3-Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals

2015 ◽  
Vol 127 (10) ◽  
pp. 3051-3055 ◽  
Author(s):  
Ichiro Hisaki ◽  
Shoichi Nakagawa ◽  
Norimitsu Tohnai ◽  
Mikiji Miyata
Keyword(s):  
Molecular Crystals ◽  
Hexagonal Network ◽  
Hydrogen Bonded

scholarly journals The trans/cis photoisomerization in hydrogen bonded complexes with stability controlled by substituent effects: 3-(6-aminopyridin-3-yl)acrylate case study

RSC Advances ◽  
2018 ◽  
Vol 8 (42) ◽  
pp. 23698-23710 ◽  
Author(s):  
Adam Kwiatkowski ◽  
Beata Jędrzejewska ◽  
Marek Józefowicz ◽  
Izabela Grela ◽  
Borys Ośmiałowski
Keyword(s):  
Acrylic Acid ◽  
Substituent Effects ◽  
Nmr Titration ◽  
Bonded Complexes ◽  
Hydrogen Bonded

The association of aminopyridine-based acrylic acid and its salt was studied by NMR titration experiments.

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