A SPECTROSCOPIC STUDY OF HYDROGEN BONDING IN PERFORMIC AND PERACETIC ACIDS

1952 ◽  
Vol 30 (11) ◽  
pp. 821-830 ◽  
Author(s):  
Paul A. Giguère ◽  
A. Weingartshofer Olmos
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Spectroscopic Study ◽  
Infrared Spectra ◽  
Peracetic Acid ◽  
The Other ◽  
Frequency Shifts ◽  
Vapor State ◽  
Nonpolar Solvents ◽  
Intramolecular Hydrogen

The infrared spectra of concentrated performic and peracetic acids were measured in the rock-salt region. The most significant features are theO—H stretching frequency at 3310–3350 cm−1 and the OH bending frequency at 1450 cm−1 which, for both peracids, remain essentially the same in the vapor state as in the liquid or in solution in nonpolar solvents. This is attributed to intramolecular hydrogen bonds resulting in particularly stable five-membered rings,[Formula: see text]Steric conditions in the percarboxylic group are favourable to such ring formation or chelation. From the observed frequency shifts the energy of these hydrogen bonds is estimated to be about 7 kcal. per mole. No evidence for unchelated molecules was found even in very dilute solutions of peracetic acid in nonpolar solvent nor in the vapour at low pressure and moderate temperature. Tentative assignments of the other frequencies in the spectra of the peracids are made by comparison with those of formic and acetic acids.The danger involved in handling these peracids in concentrated form is emphasized.

scholarly journals Hydrogen Bonds: Raman Spectroscopic Study

2021 ◽  
Vol 22 (10) ◽  
pp. 5380
Author(s):  
Boris A. Kolesov
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Spectroscopic Study ◽  
Raman Spectra ◽  
Temperature Region ◽  
Vibrational Frequency ◽  
Chemical Compounds ◽  
Raman Spectroscopic ◽  
Raman Spectroscopic Study ◽  
Proton Dynamics

The work outlines general ideas on how the frequency and the intensity of proton vibrations of X–H×××Y hydrogen bonding are formed as the bond evolves from weak to maximally strong bonding. For this purpose, the Raman spectra of different chemical compounds with moderate, strong, and extremely strong hydrogen bonds were obtained in the temperature region of 5 K–300 K. The dependence of the proton vibrational frequency is schematically presented as a function of the rigidity of O-H×××O bonding. The problems of proton dynamics on tautomeric O–H···O bonds are considered. A brief description of the N–H···O and C–H···Y hydrogen bonds is given.

scholarly journals Two New Polyiodides in the 4,4´-Bipyridinium Diiodide/Iodine System

2012 ◽  
Vol 67 (1) ◽  
pp. 5-10
Author(s):  
Guido J. Reiss ◽  
Martin van Megen
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Complex I ◽  
The Other ◽  
Cyclic Dimer ◽  
Water Molecules ◽  
Spectroscopic Methods ◽  
Halogen Bonds ◽  
One Dimensional ◽  
Hydroiodic Acid

The reaction of bipyridine with hydroiodic acid in the presence of iodine gave two new polyiodide-containing salts best described as 4,4´-bipyridinium bis(triiodide), C10H10N2[I3]2, 1, and bis(4,4´-bipyridinium) diiodide bis(triiodide) tris(diiodine) solvate dihydrate, (C10H10N2)2I2[I3]2 · 3 I2 ·2H2O, 2. Both compounds have been structurally characterized by crystallographic and spectroscopic methods (Raman and IR). Compound 1 is composed of I3 − anions forming one-dimensional polymers connected by interionic halogen bonds. These chains run along [101] with one crystallographically independent triiodide anion aligned and the other triiodide anion perpendicular to the chain direction. There are no classical hydrogen bonds present in 1. The structure of 2 consists of a complex I144− anion, 4,4´-bipyridinium dications and hydrogen-bonded water molecules in the ratio of 1 : 2 : 2. The I144− polyiodide anion is best described as an adduct of two iodide and two triiodide anions and three diiodine molecules. Two 4,4´-bipyridinium cations and two water molecules form a cyclic dimer through N-H· · ·O hydrogen bonds. Only weak hydrogen bonding is found between these cyclic dimers and the polyiodide anions.

Polymorphs of phenazine hexacyanoferrate(II) hydrate: supramolecular isomerism in a 2D hydrogen-bonded network

2021 ◽  
Vol 77 (2) ◽  
pp. 211-218
Author(s):  
Ivica Cvrtila ◽  
Vladimir Stilinović
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Two Dimensional ◽  
Structural Motifs ◽  
Supramolecular Isomerism ◽  
Other Hand ◽  
Π Stacking ◽  
Hydrogen Bonded

The crystal structures of two polymorphs of a phenazine hexacyanoferrate(II) salt/cocrystal, with the formula (Hphen)3[H2Fe(CN)6][H3Fe(CN)6]·2(phen)·2H2O, are reported. The polymorphs are comprised of (Hphen)2[H2Fe(CN)6] trimers and (Hphen)[(phen)2(H2O)2][H3Fe(CN)6] hexamers connected into two-dimensional (2D) hydrogen-bonded networks through strong hydrogen bonds between the [H2Fe(CN)6]2− and [H3Fe(CN)6]− anions. The layers are further connected by hydrogen bonds, as well as through π–π stacking of phenazine moieties. Aside from the identical 2D hydrogen-bonded networks, the two polymorphs share phenazine stacks comprising both protonated and neutral phenazine molecules. On the other hand, the polymorphs differ in the conformation, placement and orientation of the hydrogen-bonded trimers and hexamers within the hydrogen-bonded networks, which leads to different packing of the hydrogen-bonded layers, as well as to different hydrogen bonding between the layers. Thus, aside from an exceptional number of symmetry-independent units (nine in total), these two polymorphs show how robust structural motifs, such as charge-assisted hydrogen bonding or π-stacking, allow for different arrangements of the supramolecular units, resulting in polymorphism.

scholarly journals The infrared spectra of protic ionic liquids: performances of different computational models to predict hydrogen bonds and conformer evolution

2020 ◽  
Vol 22 (14) ◽  
pp. 7497-7506 ◽  
Author(s):  
O. Palumbo ◽  
A. Cimini ◽  
F. Trequattrini ◽  
J.-B. Brubach ◽  
P. Roy ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Ionic Liquids ◽  
Hydrogen Bonds ◽  
Dft Calculations ◽  
Infrared Spectra ◽  
Computational Models ◽  
Far Infrared ◽  
Protic Ionic Liquids ◽  
Far Infrared Spectra

DFT calculations with the ωB97-D functional reproduce hydrogen bonding features of the far-infrared spectra of diethylmethylammonium methanesulfonate and diethylmethylammonium trifluoromethanesulfonate.

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY SPECTROSCOPIC METHODS: PART VIII. THE ULTRAVIOLET AND INFRARED SPECTRA OF SOME 2,4-DINITRODIPHENYLAMINES

1964 ◽  
Vol 42 (12) ◽  
pp. 2674-2683 ◽  
Author(s):  
A. Balasubramanian ◽  
J. B. Capindale ◽  
W. F. Forbes
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Spectral Data ◽  
Intramolecular Hydrogen Bond ◽  
Infrared Spectra ◽  
Positive Charge ◽  
Spectroscopic Methods ◽  
Amino Group ◽  
Strong Type ◽  
Intramolecular Hydrogen

The ultraviolet spectra of a number of 2,4-dinitrodiphenylamines suggest that these compounds are generally non-planar in a number of different solvents. The infrared and ultraviolet spectral data in different solvents also suggest that an intramolecular hydrogen bond is present in these molecules, at least in inert solvents. There is evidence that a p-nitro substituent is necessary to increase the positive charge on the amino group sufficiently to permit it to form this fairly strong type of hydrogen bond.

THEORETICAL STUDY OF THE HYDROGEN BOND CHARACTER BETWEEN THE FNO AND HO2 RADICAL

2010 ◽  
Vol 09 (05) ◽  
pp. 925-934 ◽  
Author(s):  
QIN HE ◽  
ZHI-FENG LI
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Theoretical Study ◽  
Basis Sets ◽  
Potential Density ◽  
Geometrical Characteristics ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonding Site ◽  
Ho2 Radical ◽  
Bond Character

The hydrogen-bonding characters between FNO and HO2 radical are studied systematically with the MPWB1K method and 6-311++G (d, p), aug-cc-PVDZ as well as aug-cc-PVTZ basis sets. The relevant geometrical characteristics, energy properties, and the characters of the intramolecular hydrogen bonds have been reported in this work. In addition, the changes of electrostatic potential density are presented for further understanding the nature of hydrogen bonds and the preference of F atom as the hydrogen-bonding site.

More examples of the 15-crown-5...H2O—M—OH2...15-crown-5 motif, M = Al3+, Cr3+ and Pd2+

2010 ◽  
Vol 66 (2) ◽  
pp. 213-221 ◽  
Author(s):  
Maxime A. Siegler ◽  
Jacob H. Prewitt ◽  
Steven P. Kelley ◽  
Sean Parkin ◽  
John P. Selegue ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Lattice Water Molecule ◽  
Literature Survey ◽  
The Other ◽  
Water Molecules ◽  
Lattice Water ◽  
Hydrogen Bonding Pattern ◽  
Hydrogen Bonded

Five structures of co-crystals grown from aqueous solutions equimolar in 15-crown-5 (or 15C5) and [M(H2O)6](NO3) n , M = Al3+, Cr3+ and Pd2+, are reported. The hydrogen-bonding patterns in all are similar: metal complexes including the fragment trans-H2O—M—OH2 alternate with 15C5 molecules, to which they are hydrogen bonded, to form stacks. A literature survey shows that this hydrogen-bonding pattern is very common. In each of the two polymorphs of the compound [Al(H2O)6](NO3)3·15C5·4H2O there are two independent cations; one forms hydrogen bonds directly to the 15C5 molecules adjacent in the stack, while the other cation is hydrogen-bonded to two water molecules that act as spacers in the stack. These stacks are then crosslinked by hydrogen bonds formed by the three nitrate counterions and the three lattice water molecules. The hydrogen-bonded stacks in [Cr(H2O)5(NO3)](NO3)2·1.5(15C5)·H2O are discrete rather than infinite; each unit contains two Cr3+ complex cations and three 15C5 molecules. These units are again crosslinked by the uncoordinated nitrate ions and a lattice water molecule. In [Pd(H2O)2(NO3)2]·15C5 the infinite stacks are electrically neutral and are not crosslinked. In [Pd(H2O)2(NO3)2]·2(15C5)·2H2O·2HNO3 a discrete, uncharged unit containing one Pd complex and two 15C5 molecules is `capped off' at either end by a lattice water molecule and an included nitric acid molecule. In all five structures the infinite stacks or discrete units form an array that is at least approximately hexagonal.

The influence of hydrogen bonding on the character of N—H and C=O stretching modes in 2-thiopyrrole-1,2-dicarboximide

1984 ◽  
Vol 62 (9) ◽  
pp. 1845-1849 ◽  
Author(s):  
Shanker Ram
Keyword(s):  
Hydrogen Bonding ◽  
Transition Temperature ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Spectral Data ◽  
Infrared Spectra ◽  
Cyclic Dimer ◽  
Dilute Solutions ◽  
Two Phases ◽  
Thermodynamical Functions

The infrared spectra (200–4000 cm−1) of 2-thiopyrrole-1,2-dicarboximide (TPH) in solid and solution forms have been measured as a function of temperature, and a direct correlation has been obtained between the two phases and the type and extent of hydrogen bonding. It is suggested that TPH exists as cyclic dimer in the solid state (below 310 K) and in dilute solutions by the formation of two equivalent hydrogen bonds. At the transition temperature, ~310 K, the cyclic dimer undergoes to the open-cyclic dimer and persists in this structure till 410 K. In addition, the thermodynamical functions ΔH0, and ΔS0 have been estimated using the spectral data in solution.

Intra- and inter-molecular hydrogen bonding in diphytanylglycerol phospholipids: an infrared spectroscopic investigation

1990 ◽  
Vol 68 (1) ◽  
pp. 266-273 ◽  
Author(s):  
L. C. Stewart ◽  
M. Kates ◽  
P. W. Yang ◽  
H. H. Mantsch
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Intramolecular Hydrogen Bond ◽  
Membrane Lipids ◽  
Head Group ◽  
Exact Nature ◽  
Oh Groups ◽  
Intramolecular Hydrogen ◽  
Phosphate Groups

A series of diphytanylglycerol phospholipids, i.e., diphytanylglycerol phosphate (PA), diphytanylglycerol phosphoglycerophosphate (PGP), the tri- and tetra-methyl derivatives of PGP, and the 2-deoxyglycerol analogue of PGP (dPGP) were studied by Fourier transform infrared spectroscopy. The use of the "deoxy" and methylated analogues of PGP, as well as that of PA and PGP of varying degrees of ionization, allowed the assignment of characteristic infrared bands associated with the phosphate groups. Analysis of these phosphate bands showed that at neutral pH, each of the two phosphate moieties in PGP is singly ionized, whereas in dPGP the phosphomonoester is doubly ionized. This is a consequence of the marked increase in the pK of one of the P-OH groups on the terminal phosphate of PGP (pK > 11), owing to the formation of an intramolecular hydrogen bond between the head group glycerol hydroxyl and the phosphate groups of PGP. Such an intramolecular hydrogen bond can not be formed by the dPGP analogue, and thus both negative charges in dPGP are located at the terminal phosphomonoester group. The O=P—OH groups of PGP also forms a network of intermolecular hydrogen bonds, the exact nature of which depends on concentration and degree of ionization. The possibility of a complex network of hydrogen bonds within (intramolecular) and between (intermolecular) anionic membrane lipids such as that found in PGP, is consistent with the hypothesis that these lipids function as proton-conducting pathways in membranes.Key words: phospholipids, infrared, hydrogen bonding, phosphatidylglycerophosphate, 2-deoxyphosphatidylglycerophosphate.

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