Quantum chemical calculations with the AIM approach applied to the π-interactions between hydrogen chalcogenides and naphthalene

RSC Advances ◽  
2016 ◽  
Vol 6 (55) ◽  
pp. 49651-49660 ◽  
Author(s):  
Satoko Hayashi ◽  
Yuji Sugibayashi ◽  
Waro Nakanishi
Keyword(s):  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Π Interactions

The nature of π-interactions in (EH2)n–*–π(C10H8) (n = 1 and 2: E = O, S, Se and Te) is elucidated with QTAIM-DFA. They have the character of the vdW-nature of the pure-CS interactions, except for HHTe–*–π(C10H8), which seems stronger than others.

Problems with a conformation assignment of aryl-substituted resorc[4]arenes

2011 ◽  
Vol 76 (10) ◽  
pp. 1199-1222 ◽  
Author(s):  
Jakub Kaminský ◽  
Hana Dvořáková ◽  
Jan Štursa ◽  
Jitka Moravcová
Keyword(s):  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Quantum Chemical Calculations ◽  
Dynamic Process ◽  
Quantum Chemical ◽  
Energy Barrier ◽  
Π Interactions ◽  
Temperature Range ◽  
Acid Catalyzed

Acid-catalyzed condensation of resorcinol with 3,5-diisopropoxybenzaldehyde and 3,5-dihydroxybenzaldehyde afforded aryl substituted resorc[4]arenes 1a and 1b, respectively. All 16 hydroxyls in 1b were acetylated providing resorc[4]arene 1c. The conformational behaviour of 1a, 1b and 1c was studied by NMR spectroscopy and quantum chemical calculations. It was found that the stabilization of their conformations is an effect of competing π-π and OH-π interactions, hydrogen bonding and steric features, respectively. As a result, C2 symmetrical boat conformations 1a, 1b and 1c with aryls in axial positions were identified in all cases. In case of 1c also the formation of C2 symmetrical conformation with aryls in equatorial positions (boat-eq) was identified. Moreover, compounds 1a and 1b being able to create hydrogen bonds, adopt also symmetrical C4 crown conformations. For 1c(boat-ax), the boat-boat conversion with energy barrier of 80 kJ/mol was observed, while the 1c(boat-eq) was found to be rigid in the whole accessible temperature range. Both conformers of 1c exhibit also second dynamic process – rotation of bridge aryl rings (ΔG‡ = 66 kJ/mol).

Unusual structure of a biphenyl fragment: the important role of weak interactions

2019 ◽  
Vol 75 (11) ◽  
pp. 1454-1458 ◽  
Author(s):  
Alexander Vashchenko ◽  
Vladimir Smirnov ◽  
Nadezhda Semenova ◽  
Elena Schmidt
Keyword(s):  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Weak Interactions ◽  
Intramolecular Interactions ◽  
Atoms In Molecules ◽  
Unusual Structure ◽  
X Ray ◽  
Π Interactions ◽  
The Moment

1,5-Bis([1,1′-biphenyl]-4-yl)-5-hydroxy-3-methylheptane-1,6-dione, C32H30O3, was investigated by X-ray analysis, quantum chemical calculations and AIM (atoms in molecules) analysis. It was shown that four intramolecular C—H...π forces are established between the two biphenyl fragments. C—H...π interactions lead to a bending of the biphenyl part. The energy of the intramolecular interactions was estimated and the exclusive role of the moment of force was established.

scholarly journals Synthesis, structure and dispersion interactions in bis(1,8-naphthalendiyl)distibine

2017 ◽  
Vol 46 (28) ◽  
pp. 9227-9234 ◽  
Author(s):  
C. Ganesamoorthy ◽  
S. Heimann ◽  
S. Hölscher ◽  
R. Haack ◽  
C. Wölper ◽  
...  
Keyword(s):  
Solid State ◽  
Quantum Chemical Calculations ◽  
Intermolecular Interactions ◽  
Quantum Chemical ◽  
Dispersion Interactions ◽  
Π Interactions ◽  
Electrostatic Contribution

Naph2Sb21shows intermolecular interactions in the solid state. Quantum chemical calculations of1and the lighter (P, As) and heavier (Bi) congeners showed that intermolecular E⋯E interactions (E = P, As, Sb, Bi) are dispersion dominated, while E⋯π interactions additionally contained a significant electrostatic contribution.

Discovery of a Difluoroglycine Synthesis Method through Quantum Chemical Calculations

2020 ◽  
Author(s):  
Tsuyoshi Mita ◽  
Yu Harabuchi ◽  
Satoshi Maeda
Keyword(s):  
Quantum Chemical Calculations ◽  
Experimental Verification ◽  
Quantum Chemical ◽  
Synthesis Method ◽  
Target Product ◽  
Systematic Exploration ◽  
Hands On ◽  
Retrosynthetic Analysis ◽  
Synthetic Routes ◽  
Verification Process

The systematic exploration of synthetic pathways to afford a desired product through quantum chemical calculations remains a considerable challenge. In 2013, Maeda et al. introduced ‘quantum chemistry aided retrosynthetic analysis’ (QCaRA), which uses quantum chemical calculations to search systematically for decomposition paths of the target product and propose a synthesis method. However, until now, no new reactions suggested by QCaRA have been reported to lead to experimental discoveries. Using a difluoroglycine derivative as a target, this study investigated the ability of QCaRA to suggest various synthetic paths to the target without relying on previous data or the knowledge and experience of chemists. Furthermore, experimental verification of the seemingly most promising path led to the discovery of a synthesis method for the difluoroglycine derivative. The extent of the hands-on expertise of chemists required during the verification process was also evaluated. These insights are expected to advance the applicability of QCaRA to the discovery of viable experimental synthetic routes.

Discovery of a Difluoroglycine Synthesis Method through Quantum Chemical Calculations

2020 ◽  
Author(s):  
Tsuyoshi Mita ◽  
Yu Harabuchi ◽  
Satoshi Maeda
Keyword(s):  
Quantum Chemical Calculations ◽  
Experimental Verification ◽  
Quantum Chemical ◽  
Synthesis Method ◽  
Target Product ◽  
Systematic Exploration ◽  
Hands On ◽  
Retrosynthetic Analysis ◽  
Synthetic Routes ◽  
Verification Process

The systematic exploration of synthetic pathways to afford a desired product through quantum chemical calculations remains a considerable challenge. In 2013, Maeda et al. introduced ‘quantum chemistry aided retrosynthetic analysis’ (QCaRA), which uses quantum chemical calculations to search systematically for decomposition paths of the target product and propose a synthesis method. However, until now, no new reactions suggested by QCaRA have been reported to lead to experimental discoveries. Using a difluoroglycine derivative as a target, this study investigated the ability of QCaRA to suggest various synthetic paths to the target without relying on previous data or the knowledge and experience of chemists. Furthermore, experimental verification of the seemingly most promising path led to the discovery of a synthesis method for the difluoroglycine derivative. The extent of the hands-on expertise of chemists required during the verification process was also evaluated. These insights are expected to advance the applicability of QCaRA to the discovery of viable experimental synthetic routes.

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