Intramolecular hydrogen bonds involving organic fluorine in the derivatives of hydrazides: an NMR investigation substantiated by DFT based theoretical calculations

Literature Information

Publication Date 2015-05-13
DOI 10.1039/C5CP01505G
Impact Factor 3.676
Authors

Sandeep Kumar Mishra, N. Suryaprakash


View Original

Abstract

The rare examples of intramolecular hydrogen bonds (HB) of the type the N–H⋯F–C, detected in a low polarity solvent in the derivatives of hydrazides, by utilizing one and two-dimensional solution state multinuclear NMR techniques, are reported. The observation of through-space couplings, such as, 1hJFH, and 1hJFN, provides direct evidence for the existence of intra-molecular HB. Solvent induced perturbations and the variable temperature NMR experiments unambiguously establish the presence of intramolecular HB. The existence of multiple conformers in some of the investigated molecules is also revealed by two dimensional HOESY and 15N–1H HSQC experiments. The 1H DOSY experimental results discard any possibility of self or cross dimerization of the molecules. The derived NMR experimental results are further substantiated by Density Function Theory (DFT) based Non Covalent Interaction (NCI), and Quantum Theory of Atom in Molecule (QTAIM) calculations. The NCI calculations served as a very sensitive tool for detection of non-covalent interactions and also confirm the presence of bifurcated HBs.

Related Literature

The DNA-forming properties of 6-selenoguanine

Carles Curutchet, F. Javier Luque

2013-11-11 Paper

DOI: 10.1039/C3CP53885K

Red-light initiated atmospheric reactions of vibrationally excited molecules

D. J. Donaldson

2013-11-07 Perspective

DOI: 10.1039/C3CP53543F

Energetic behavior of the pure silica ITQ-12 (ITW) zeolite under high pressure water intrusion

Ismail Khay, Lydie Tzanis, T. Jean Daou, Habiba Nouali, Andrey Ryzhikov, Joël Patarin

2013-10-15 Paper

DOI: 10.1039/C3CP53570C

Experimental and theoretical study of the distance dependence of metal-enhanced fluorescence, phosphorescence and delayed fluorescence in a single system

Hirdyesh Mishra, Buddha L. Mali, Jan Karolin, Anatoliy I. Dragan, Chris D. Geddes

2013-09-20 Paper

DOI: 10.1039/C3CP50633A

Effects of resonant excitation, pulse duration and intensity on photoelectron imaging of a dianion

Daniel A. Horke, Jan R. R. Verlet

2013-09-23 Paper

DOI: 10.1039/C3CP53235F

Metal-enhanced fluorescence

Chris D. Geddes

2013-10-02 Editorial

DOI: 10.1039/C3CP90129G

Velocity map imaging of ion–molecule reactions

2013-10-17 Perspective

DOI: 10.1039/C3CP53405G

Simultaneous induction of high level thermal and visible-light catalytic activities to titanium(iv) oxide by surface modification with cobalt(iii) oxide clusters

Qiliang Jin, Hironori Yamamoto, Kotaro Yamamoto, Musashi Fujishima, Hiroaki Tada

2013-10-14 Paper

DOI: 10.1039/C3CP54304H

State-to-state resolved differential cross sections for rotationally inelastic scattering of ND3 with He

Ondřej Tkáč, Ashim Kumar Saha, Jolijn Onvlee, Chung-Hsin Yang, Gautam Sarma, Chandan Kumar Bishwakarma, Sebastiaan Y. T. van de Meerakker, Ad van der Avoird, David H. Parker, Andrew J. Orr-Ewing

2013-09-25 Paper

DOI: 10.1039/C3CP53550A

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

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.