Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

Шишкин, Олег В.; Konovalova, Irina S.; Gorb, Leonid; Leszczyński, Jerzy

doi:10.1007/s11224-009-9412-5

Cited by 31 publications

(27 citation statements)

References 29 publications

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“…DFT and MP2 approaches with a large variety of basis sets have been applied to water/pyridine and other water/nitrogen‐base complexes and clusters of various stoichiometries . The 1:1 water/pyridine complex is depicted as having a C s structure, reported also for the water/collidine complexes: the symmetry plane is perpendicular to the molecular plane of pyridine, and the complex exhibits an approximately linear O–H⋯N hydrogen bond, with the pyridine nitrogen acting as the proton acceptor .…”

Section: Discussionmentioning

confidence: 99%

¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

Lomas

2015

Magnetic Reson in Chemistry

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Proton nuclear magnetic resonance (NMR) shifts of aliphatic alcohols in hydrogen bonding solvents have been computed on the basis of density functional theory by applying the gauge-including atomic orbital method to geometry-optimized alcohol/solvent complexes. The OH proton shifts and hydrogen bond distances for methanol or ethanol complexed with pyridine depend very much on the functional employed and very little on the basis set, provided it is sufficiently large to give the correct quasi-linear hydrogen bond geometry. The CH proton shifts are insensitive to both the functional and the basis set. NMR shifts for all protons in several alcohol/pyridine complexes are calculated at the Perdew, Burke and Ernzerhof PBE0/cc-pVTZ//PBE0/6-311 + G(d,p) level in the gas phase. The results correlate with the shifts for the pyridine-complexed alcohols, determined by analysing data from the NMR titration of alcohols against pyridine. More pragmatically, computed shifts for a wider range of alcohols correlate with experimental shifts in neat pyridine. Shifts for alcohols in dimethylsulfoxide, based on the corresponding complexes in the gas phase, correlate well with the experimental values, but the overall root mean square difference is high (0.23 ppm), shifts for the OH, CHOH and other CH protons being systematically overestimated, by averages of 0.42, 0.21 and 0.06 ppm, respectively. If the computed shifts are corrected accordingly, a very good correlation is obtained with a gradient of 1.00 ± 0.01, an intercept of 0.00 ± 0.02 ppm and a root mean square difference of 0.09 ppm. This is a modest improvement on the result of applying the CHARGE programme to a slightly different set of alcohols. Some alcohol complexes with acetone and acetonitrile were investigated both in the gas phase and in a continuum of the relevant solvent.

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Section: Discussionmentioning

confidence: 99%

¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

Lomas

2015

Magnetic Reson in Chemistry

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“…Moreover, it can direct many chemical, physical, and biochemical processes. In recent years, a large number of experimental and theoretical studies on the structure, stability and thermodynamic properties have been performed on the hydrogen bond complexes [14][15][16][17][18][19]. On the other hand, the structures and properties of aqueous solutions of organic compounds are of considerable interest in the study hydrogen bond, hydrophobic and hydrophilic interactions between organic molecules and water.…”

Section: Introductionmentioning

confidence: 99%

A combined experimental and theoretical approach to the study of hydrogen bond interaction in the binary mixture of N-methylimidazole with water

Huang

Liu

et al. 2012

The Journal of Chemical Thermodynamics

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“…Parameters Methods different complexes is vast [20][21][22][23][24][25][26], quantum chemical study of hydrogen-bond interaction between water and glycols other than ethylene glycol and trimethylene glycol has not been reported so far. Electronic structure-based studies on hydrogen-bond formation between water and glycol having ether functional group (C-O-C) (e.g., diethylene glycol, triethylene glycol and dipropylene glycol) have not been performed till date.…”

Section: Systemmentioning

confidence: 99%

Stability Analysis and Frontier Orbital Study of Different Glycol and Water Complex

Pal

Kundu

2013

ISRN Physical Chemistry

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A detailed theoretical study of hydrogen-bond formation in different polyethylene glycol + water complex and dipropylene glycol + water have been performed by Hartree Fock (HF) method, second-order Møller-Plesset perturbation theory (MP2), and density functional theory (DFT) using 6-31++G(d,p) basis set. B3LYP DFT-D, WB97XD, M06, and M06-2X functionals have been used to describe highly dispersive hydrogen-bond formation appropriately. Geometrical parameters, interaction energies, deformation energies, deviation of potential energy curves of hydrogen bonded O-H from that of free O-H, frontier orbitals, and charge transfer have been studied to analyze stability and nature of hydrogen bond formation of various glycol and water complexes. It is found that WB97XD is best among all the applied DFT functionals to describe hydrogen bond interaction, and intermolecular hydrogen bonds have higher covalent character and accordingly higher strength when glycol acts as proton donor for glycol + 1 water complex system.

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Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

Cited by 31 publications

References 29 publications

¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

A combined experimental and theoretical approach to the study of hydrogen bond interaction in the binary mixture of N-methylimidazole with water

Stability Analysis and Frontier Orbital Study of Different Glycol and Water Complex

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Novel type of mixed O–H···N/O–H···π hydrogen bonds: monohydrate of pyridine

Cited by 31 publications

References 29 publications

1H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

1H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

A combined experimental and theoretical approach to the study of hydrogen bond interaction in the binary mixture of N-methylimidazole with water

Stability Analysis and Frontier Orbital Study of Different Glycol and Water Complex

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Product

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¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts

¹H NMR spectra of alcohols in hydrogen bonding solvents: DFT/GIAO calculations of chemical shifts