Through-space interactions between face-to-face, center-to-edge oriented arenes: importance of polar–π effects
Literature Information
Franco Cozzi, Rita Annunziata, Maurizio Benaglia, Mauro Cinquini, Laura Raimondi, Kim K. Baldridge, Jay S. Siegel
Two series of conformationally restricted polycyclic compounds (1–3 and 4–7) have been synthesized as model systems for studying the through-space interactions between face-to-face, center-to-edge (parallel-offset) oriented arenes. These compounds feature different X substituents on one of the interacting rings. By monitoring the variation of the ΔG≠ for the rotation around the aryl–aryl bond in 1–7 as a function of X by 2D [1H,1H] EXSY NMR spectroscopy, it was found that the barriers increase on passing from electron-donating to electron-withdrawing substituted derivatives. Quantum mechanical calculations [MP2/DVZ (2d,p)//B3LYP/DVZ(2d,p)] gave barrier values and variations in agreement with the experimental data. The results are consistent with a repulsive arene–arene interaction dominated by electrostatic effects.
Related Literature
Novel intermolecular carbon radical addition to a nitrone: asymmetric synthesis of α-amino acids
Masafumi Ueda, Hideto Miyabe, Masako Teramachi, Okiko Miyata, Takeaki Naito
DOI: 10.1039/B211570K
A rare ether-bridged cobalt complex which gives rise to an unusual ‘serpentine’ metal–ligand binding motif
Garry Mund, Andrea J. Gabert, Raymond J. Batchelor, James F. Britten, Daniel B. Leznoff
DOI: 10.1039/B208221G
Configuration assignment in small organic moleculesvia residual dipolar couplings
Alfonso Mangoni, Veronica Esposito, Antonio Randazzo
DOI: 10.1039/B210454G
Mechanistic studies on ethylene silylation with chlorosilanes catalysed by ruthenium complexes
Sébastien Lachaize, Sylviane Sabo-Etienne, Bruno Donnadieu, Bruno Chaudret
DOI: 10.1039/B210552G
In control of the speed of rotation in molecular motors. Unexpected retardation of rotary motion
Edzard M. Geertsema, Nagatoshi Koumura, Matthijs K. J. ter Wiel, Auke Meetsma, Ben L. Feringa
DOI: 10.1039/B208323J
Supported ionic liquid catalysis investigated for hydrogenation reactions
Christian P. Mehnert, Edmund J. Mozeleski, Raymond A. Cook
DOI: 10.1039/B210214E
Development of silver film viathermal decomposition of layered silver alkanecarboxylates for surface-enhanced Raman spectroscopy
Seung Joon Lee, Kwan Kim
DOI: 10.1039/B210217J
A novel synthesis of tetrahydrofuranvia alkoxy radical cyclisation
Masahiro Yokota, Masahiro Toyota, Masataka Ihara
DOI: 10.1039/B211568A
Novel Cr-PNP complexes as catalysts for the trimerisation of ethylene
David S. McGuinness, Peter Wasserscheid, Wilhelm Keim, Chunhua Hu, Ulli Englert, John T. Dixon, Cronje Grove
DOI: 10.1039/B210878J
A novel three-dimensional coordination polymer constructed with mixed-valence dimeric copper(i,ii) units
Katsunori Mochizuki, Ho-Chol Chang, Xiao-Ming Chen, Ying Li, Susumu Kitagawa
DOI: 10.1039/B210914J
You might also like
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.












![(2R,6S)-6-[(Benzyloxy)methyl]-4-{[(2-methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid structure (2R,6S)-6-[(Benzyloxy)methyl]-4-{[(2-methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid structure](https://static.chemtradehub.com/structs/109/1093085-91-6-3382.webp)

