The intramolecular NH···Cl hydrogen bond in urea derivatives containing the o-chlorophenyl group

Mido, Yoshiyuki; Okuno, Takashi

doi:10.1016/0022-2860(82)85230-7

Cited by 22 publications

(16 citation statements)

References 7 publications

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“…Consequent to the binding nature of fluorinated molecules with enzyme active sites, intermolecular hydrogen bonds of the type X-H···F-C (X = O, N) are highly significant, especially in bio-inorganic and medicinal chemistry [ 80 , 81 , 82 , 83 , 84 ]. Despite all its importance in various branches of chemistry and biology, there is limited exploration of organic fluorine-involved HBs, attributed mainly to the fact flourine hardly ever accepts intramolecular HB [ 85 , 86 , 87 , 88 , 89 ]. The present review summarizes the work carried out by authors’ laboratory in recent years, taken directly from their published work.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Mishra

Suryaprakash

2017

Molecules

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The combined utility of many one and two dimensional NMR methodologies and DFT-based theoretical calculations have been exploited to detect the intramolecular hydrogen bond (HB) in number of different organic fluorine-containing derivatives of molecules, viz. benzanilides, hydrazides, imides, benzamides, and diphenyloxamides. The existence of two and three centered hydrogen bonds has been convincingly established in the investigated molecules. The NMR spectral parameters, viz., coupling mediated through hydrogen bond, one-bond NH scalar couplings, physical parameter dependent variation of chemical shifts of NH protons have paved the way for understanding the presence of hydrogen bond involving organic fluorine in all the investigated molecules. The experimental NMR findings are further corroborated by DFT-based theoretical calculations including NCI, QTAIM, MD simulations and NBO analysis. The monitoring of H/D exchange with NMR spectroscopy established the effect of intramolecular HB and the influence of electronegativity of various substituents on the chemical kinetics in the number of organic building blocks. The utility of DQ-SQ technique in determining the information about HB in various fluorine substituted molecules has been convincingly established.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Mishra

Suryaprakash

2017

Molecules

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“…Catalyst 2 was purchased from Aldrich. Catalysts 1 ,15 3a ,16 3b ,17 3c ,18 3d ,19 3e ,20 4 ,16 6 ,21 7 ,22 8 ,13e 9 ,23 10 13a and 11 14 were prepared according to literature procedures. Catalyst 3f was synthesized in this work.…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic Three‐Component Reactions of Pyruvate, Aldehyde and Aniline by Hydrogen‐Bonding Catalysts

Deng

Luo

et al. 2008

Eur J Org Chem

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Keywords: Hydrogen bonds / Multicomponent reactions / Chirality / Phosphoric acids / Thioureas / Asymetric catalysis Hydrogen-bonding catalysts have been found to catalyze one-pot three-component reactions of pyruvate, anilines and aldehydes to afford versatile 3-amino-1,5-dihydro-2H-pyrrol-2-ones in high yields. Both, thioureas and phosphoric acids are viable catalysts for these reactions and have comparable activity. The corresponding chiral thioureas and phosphoric

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“…The nuclear magnetic resonance (NMR) and X-ray crystallographic studies have been reported on the N-H … F-C HB in foldamers and benzanilides 37,38 . It is also well known that organic fluorine generally does not get involved in the intramolecular HB [39][40][41][42][43][44][45] . The report by Dunitz and co-workers concluded that ''organic fluorine hardly ever accepts hydrogen bonds'' [46][47][48][49] .…”

Section: Introductionmentioning

confidence: 99%

Organic fluorine involved intramolecular hydrogen bonds in the derivatives of imides: NMR evidence corroborated by DFT based theoretical calculations

Mishra

Suryaprakash

2015

RSC Adv.

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The rare occurrence of the intramolecular Hydrogen bonds (HBs) of the type N−H•••F−C are detected in the derivatives of imides in a low polarity solvent by using multi-dimensional and multinuclear NMR experiments. The observation of 1h JFH, 2h JFN, and 2h JFF, where the spin magnetization is transmitted through-space among the interacting NMR active nuclei, provided the strong and unambiguous evidence for the existence of intra-molecular HB. The variation of chemical shifts of labile protons on physical conditions, such as, solvent dilution and systematic alteration of temperature confirmed the presence of weak interactions through intramolecular HBs in all the investigated fluorine substituted molecules. The self or cross dimerization of molecules is unequivocally discarded by the analysis of the rates of diffusion obtained using pseudo-two dimensional DOSY experiments. The Density Function Theoretical (DFT) calculations based on Quantum Theory of Atoms in Molecules (QTAIM) and Non Covalent Interaction (NCI), are in close agreement with the NMR experimental findings.

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The intramolecular NH···Cl hydrogen bond in urea derivatives containing the o-chlorophenyl group

Cited by 22 publications

References 7 publications

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Organocatalytic Three‐Component Reactions of Pyruvate, Aldehyde and Aniline by Hydrogen‐Bonding Catalysts

Organic fluorine involved intramolecular hydrogen bonds in the derivatives of imides: NMR evidence corroborated by DFT based theoretical calculations

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