NH+–F Hydrogen Bonding in a Fluorinated “Proton Sponge” Derivative: Integration of Solution, Solid-State, Gas-Phase, and Computational Studies

2011 ◽  
Vol 76 (19) ◽  
pp. 7975-7984 ◽  
Author(s):  
Michael T. Scerba ◽  
Christopher M. Leavitt ◽  
Matthew E. Diener ◽  
Andrew F. DeBlase ◽  
Timothy L. Guasco ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Gas Phase ◽  
Computational Studies ◽  
Proton Sponge

Insights into the C–H⋯F–C hydrogen bond by Cambridge Structural Database analyses and computational studies

RSC Advances ◽  
2015 ◽  
Vol 5 (34) ◽  
pp. 26932-26940 ◽  
Author(s):  
Sagarika Dev ◽  
Sudeep Maheshwari ◽  
Angshuman Roy Choudhury
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Ab Initio ◽  
Gas Phase ◽  
Cambridge Structural Database ◽  
Computational Studies ◽  
Structural Database

C–H⋯F–C hydrogen bonding is analysed among fluorinated ethenes using ab initio calculations in the gas phase to understand the nature, strength and directionality of these interactions.

scholarly journals 1,8-Bis(dimethylamino)naphthyl-2-ketimines: Inside vs outside protonation

2018 ◽  
Vol 14 ◽  
pp. 2940-2948 ◽  
Author(s):  
A S Antonov ◽  
A F Pozharskii ◽  
P M Tolstoy ◽  
A Filarowski ◽  
O V Khoroshilova
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Gas Phase ◽  
Methoxy Group ◽  
Proton Sponge ◽  
Hindered Rotation ◽  
Aromatic Substituent ◽  
Imino Nitrogen ◽  
X Ray ◽  
Methoxy Groups

The structure and protonation behaviour of four ortho-arylketimines of 1,8-bis(dimethylamonio)naphthalene with a different number of methoxy groups in an aromatic substituent were investigated in solution by NMR (acetone, DMSO, MeCN), in solid state by X-ray analysis and in the gas phase by DFT calculations. Both mono- and diprotonated species were considered. It has been shown that E-isomers of neutral imines can be stabilised by an intramolecular C=N−H···OMe hydrogen bond with a neighbouring methoxy group. Electron-donating OMe groups dramatically increase the basicity of the imino nitrogen, forcing the latter to abstract a proton from the proton sponge moiety in monoprotonated forms. The participation of the out-inverted and protonated 1-NMe2 group in the Me2N−H···NH=C hydrogen bond is experimentally demonstrated. It was shown that the number and position of OMe groups in the aromatic substituents strongly affects the rate of the internal hindered rotation of the NH2 + fragment in dications.

Solid-state and gas-phase structures of two conformers of N-(4-methylphenyl)-N′,N′′-bis(morpholinyl) phosphoric triamide; insights from X-ray crystallography and DFT calculations

2011 ◽  
Vol 67 (3) ◽  
pp. 238-243 ◽  
Author(s):  
Khodayar Gholivand ◽  
Hamid Reza Mahzouni
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Dft Calculations ◽  
Gas Phase ◽  
Bond Critical Point ◽  
X Ray ◽  
X Ray Crystallography ◽  
Equal Chance ◽  
Phosphoric Triamide ◽  
Hydrogen Bonded

A phosphoric triamide with the formula (4-CH3—C6H4NH)P(O)(NC4H8O)2 has been synthesized and characterized. X-ray crystallography at 120 K reveals that the title compound is composed of two symmetrically independent molecules in the solid state. Density functional theory (DFT) calculations reveal that two conformers A and B are very close to each other from an energy point of view. Thus there is equal chance that the presence of two conformers in the lattice may lead to hydrogen-bonded chains with an ABABAB arrangement. Hydrogen bonds of the type OP...H—N (OP being the phosphoryl O atom) are established between the two conformers with binding energies of −18.8 and −20.3 kJ mol−1 (at B3LYP/6–31+G*). The electronic delocalization LP(OP) → σ*(N—H), LP(OP) being the lone pair of OP, leads to a decrease in the strength of the N—H bond during hydrogen bonding between the conformers. The charge density (ρ) at the bond critical point (b.c.p.) of N—H decreases by ∼ 0.012–0.014 e Å–3 when the molecule participates in hydrogen bonding. This may explain the red shift of the ν(N—H) stretching frequency from a single molecule in the gas phase to a hydrogen-bonded one in the solid state.

scholarly journals Experimental and Computational Studies on the Gas-Phase Acidity of 5,5-Dialkyl Barbituric Acids

2021 ◽  
Author(s):  
Juan Z. Dávalos-Prado ◽  
Javier González ◽  
Josep M. Oliva-Enrich ◽  
Emma J. Urrunaga ◽  
Alexsandre F. Lago
Keyword(s):  
Gas Phase ◽  
Computational Studies ◽  
Gas Phase Acidity

Spontaneous Generation of Stable Pnictinyl Radicals from “Jack-in-the-Box” Dipnictines:  A Solid-State, Gas-Phase, and Theoretical Investigation of the Origins of Steric Stabilization1

2001 ◽  
Vol 123 (37) ◽  
pp. 9045-9053 ◽  
Author(s):  
Sarah L. Hinchley ◽  
Carole A. Morrison ◽  
David W. H. Rankin ◽  
Charles L. B. Macdonald ◽  
Robert J. Wiacek ◽  
...  
Keyword(s):  
Solid State ◽  
Gas Phase ◽  
Theoretical Investigation ◽  
Spontaneous Generation

Solid-state 17O NMR and computational studies of terminal transition metal oxo compounds

2012 ◽  
Vol 3 (2) ◽  
pp. 391-397 ◽  
Author(s):  
Jianfeng Zhu ◽  
Takuya Kurahashi ◽  
Hiroshi Fujii ◽  
Gang Wu
Keyword(s):  
Solid State ◽  
Transition Metal ◽  
Computational Studies ◽  
17O Nmr ◽  
Oxo Compounds
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