Effect of aromatic ring fluorination on CH⋯π interactions: microwave spectrum and structure of the 1,2-difluorobenzene⋯acetylene dimer

Literature Information

Publication Date 2016-08-17
DOI 10.1039/C6CP04737H
Impact Factor 3.676
Authors

Anuradha G. Akmeemana, Justin M. Kang, Rachel E. Dorris, Rebecca D. Nelson, Ashley M. Anderton, Rebecca A. Peebles, Sean A. Peebles, Nathan A. Seifert, Brooks H. Pate


View Original

Abstract

Rotational spectra for the normal isotopic species and for six additional isotopologues of the 1,2-difluorobenzene⋯acetylene (C6H4F2⋯HCCH) weakly bound dimer have been assigned in the 6–18 GHz region using chirped-pulse Fourier-transform microwave spectroscopy. This is the third complex in a series of fluorinated benzene⋯acetylene dimers. In 1,2-difluorobenzene⋯HCCH, the H⋯π distance (2.725(28) Å) is longer by about 0.23 Å, and the estimated binding energy (EB = 2.3(6) kJ mol−1) is weaker by about 1.8 kJ mol−1, than in the previously studied fluorobenzene⋯HCCH complex. In addition, in 1,2-difluorobenzene⋯acetylene, HCCH tips ∼46(3)° away from perpendicular to the aromatic ring, with the H nearest the ring moving away from the fluorine atoms along the C2 axis of the monomer, while in the fluorobenzene and benzene complexes HCCH is perpendicular (benzene⋯HCCH) or nearly perpendicular (fluorobenzene⋯HCCH, ∼7° tilt) to the ring plane. Results from ab initio and DFT calculations will be compared to an experimental structure determined from rotational constants for the DCCD and five unique 13C substituted isotopologues.

Related Literature

Moringa pod derived antioxidant dietary fibre as a quality enhancer in goat meat nuggets

Annada Das, S. Biswas, P. K. Nanda, Niloy Chatterjee, Srija Pal, Pubali Dhar, Arun K. Verma, Dipanwita Bhattacharya, Rojison Koshy, Arun K. Das

2024-01-03 Paper

DOI: 10.1039/D3FB00177F

Inside front cover

2023-11-16 Cover

DOI: 10.1039/D3FB90019C

Contents list

2024-01-25 Front/Back Matter

DOI: 10.1039/D4FB90002B

Front cover

2024-01-03 Cover

DOI: 10.1039/D4SU90001D

Exploring metal oxides for the hydrogen evolution reaction (HER) in the field of nanotechnology

Mir Sayed Shah Danish

2023-11-10 Perspective

DOI: 10.1039/D3SU00179B

Direct re-lithiation strategy for spent lithium iron phosphate battery in Li-based eutectic using organic reducing agents

Tanongsak Yingnakorn, Jennifer Hartley, Jason S. Terreblanche, Chunhong Lei, Andrew P. Abbott

2023-11-02 Paper

DOI: 10.1039/D3SU00237C

Recent advances in semiconductor heterojunctions: a detailed review of the fundamentals of photocatalysis, charge transfer mechanism and materials

Aniket Balapure, Jayati Ray Dutta, Ramakrishnan Ganesan

2023-09-27 Review Article

DOI: 10.1039/D3LF00126A

Front cover

2023-11-16 Cover

DOI: 10.1039/D3FB90018E

The role of ceria/precious metal interfaces in catalysis

Michele Melchionna

2023-11-29 Perspective

DOI: 10.1039/D3LF00202K

You might also like

Compound Q&A

Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?

2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...

7765-11-92-(2-chloroacetamido...
Compound Q&A

Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?

2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...

62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A

What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?

(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...

1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A

What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?

2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...

917985-54-72-(5-Hexylthiophen-2...
Compound Q&A

Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?

While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...

102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A

What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?

The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...

851376-80-2tert-butyl 3-hydroxy...
Compound Q&A

How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?

Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...

6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A

How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?

(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...

351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A

What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?

Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...

10065-79-9Dibenzyl carbonimido...
Compound Q&A

What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?

The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...

74228-83-4(beta,beta,2,3,4,5,6...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.