PROTONATED CARBONYL GROUPS: III. ANTIPYRINE SALTS

1963 ◽  
Vol 41 (11) ◽  
pp. 2794-2799 ◽  
Author(s):  
Denys Cook
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Infrared Spectra ◽  
Strong Absorption ◽  
Carbonyl Groups ◽  
Correlation Field ◽  
Bending Mode ◽  
Out Of Plane ◽  
Stretching Vibration

Salts of antipyrine (2,3-dimethyl-1-phenyl-5-pyrazolone) with halogen acids have been prepared and their infrared spectra from 4000 to 650 cm−1 recorded. Stoichiometrically they are normal 1:1 salts. Identification of bands due to vibrations of the protonating hydrogen atom has been aided by replacement with deuterium atoms. It is concluded that protonation occurs at the carbonyl group from the presence of a doublet (due to correlation field splitting) at 1320 and 1220 cm−1, attributed to the in-plane hydrogen-bending mode. The OH stretching vibration gives rise to bands between 2278 and 2720 cm−1 in the different salts. Out-of-plane hydrogen-bending mode absorptions are observed between 840 and 770 cm−1.More complex acids (HAsF6 etc.) give the anomalous 2 base:1 acid salts, characterized by strong absorption below 1400 cm−1, which probably contain strong, possibly symmetrical, hydrogen bonds.

PROTONATED CARBONYL GROUPS: IV. N,N-DIMETHYLACETAMIDE SALTS

1964 ◽  
Vol 42 (12) ◽  
pp. 2721-2727 ◽  
Author(s):  
Denys Cook
Keyword(s):  
Oxygen Atom ◽  
Infrared Spectra ◽  
Deformation Mode ◽  
Carbonyl Groups ◽  
Broad Absorption ◽  
Average Value ◽  
Correlation Field ◽  
Bending Mode ◽  
Out Of Plane ◽  
Transmission Windows

The infrared spectra of N,N-dimethylacelamide salts have been recorded and are consistent with protonation at the oxygen atom, vOH is between 2 095 and 3 360 cm−1 depending on the anion. The average value of the two components of the OH in-plane hydrogen-bending mode, δOH, is 1 253 cm−1 (splitting of about 147 cm−1 due to correlation field effects). The out-of-plane hydrogen-deformation mode occurs at 928 to 761 cm−1 depending on the salt. The 1 680 and 1 400 cm−1 bands which are present in all the salts are associated chiefly with stretching the CN and CO bonds respectively, in the OCN group, though it is likely that the vibrations are somewhat mixed.Some salts of complex acids are of the 2 base: 1 acid variety with very strong broad absorption centered near 900 cm−1, containing sharp transmission windows.

PROTONATED CARBONYL GROUPS: V. α-PYRIDONE SALTS

1965 ◽  
Vol 43 (4) ◽  
pp. 749-757 ◽  
Author(s):  
Denys Cook
Keyword(s):  
Carbonyl Group ◽  
Infrared Spectra ◽  
Carbonyl Groups ◽  
Bending Vibrations ◽  
Out Of Plane ◽  
Plane Bending ◽  
Strong Acids

Salts of 1-methyl-2-pyridone and 1-methyl-2-quinolone with strong acids have been prepared and their infrared spectra recorded between 4 000 and 650 cm−1. Protonation of the carbonyl group occurs giving rise to OH stretching, in-plane and out-of-plane bending vibrations which absorb in characteristic regions of the spectrum, namely 1 900 – 3 300 cm−1 (depending on the anion), ~ 1 250 cm−1, and ~ 800 cm−1 respectively, with appropriate shifts on deuteration. Other tentative assignments are made.

Infrared study of the interactions of acetone and siliceous surfaces

1969 ◽  
Vol 47 (14) ◽  
pp. 2545-2554 ◽  
Author(s):  
J. C. McManus ◽  
Yoshio Harano ◽  
M. J. D. Low
Keyword(s):  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Boron Atom ◽  
Porous Glass ◽  
Carbonyl Groups ◽  
Infrared Study ◽  
Oh Groups ◽  
Silica Surfaces ◽  
Surface Hydroxyls ◽  
Glass Surfaces

Adsorbed acetone is held to silica surfaces by hydrogen bonds between surface silanols and the acetone carbonyl groups. Acetone is adsorbed by this mechanism on porous glass surfaces but there is also some decomposition, as shown by the increase in surface B—OH groups and by formation of new C—H absorptions at 2984 and 2940 cm−1. Experiments with boron-impregnated silica indicated that the presence of boron in the porous glass can account for this decomposition process. Bands at 1660–1670 and 1650 cm−1, observed when acetone and acetone-d6, respectively, were adsorbed on either porous glass or boron-impregnated silica, are attributed to ν(C=O) of the carbonyl group coordinated with a surface boron atom. The surface hydroxyls of both silica and porous glass could exchange with the deuterium of acetone-d6 via a mechanism involving an enol intermediate.

Effect of functional group conformation on the infrared spectra of some gem difunctional phenylethylene derivatives

1969 ◽  
Vol 47 (17) ◽  
pp. 3147-3152 ◽  
Author(s):  
D. J. Currie ◽  
C. E. Lough ◽  
F. K. McClusky ◽  
H. L. Holmes
Keyword(s):  
Absorption Band ◽  
Functional Groups ◽  
Infrared Spectra ◽  
Functional Group ◽  
Plane Deformation ◽  
Carbonyl Groups ◽  
Deformation Bands ◽  
Or Groups ◽  
Out Of Plane ◽  
Stretching Vibrations

Except for the benzalmalononitriles, two functional group stretching vibrations occur in the infrared (i.r.) spectra of the β,β-difunctional-styrenes with similar functional groups. For geometrically homogeneous compounds with dissimilar functional groups only one absorption band occurs for each functional group. The two bands for similar functional groups have been ascribed to S-cis- and S-trans-conformations of the carbonyl groups with respect to the ethylene and variation in the frequencies of each of these oriented carbonyls to rotation of the functional group or groups out of the plane of the ethylene by steric factors.Frequencies for ethylenic C—H out of plane deformation bands for β-monofunctional styrenes accorded with those already assigned to this vibration. A similar assignment could not be made for the difunctional analogues.

The Infrared Spectrum of Ethylene Oxide Clathrate Hydrate between 360 and 20 cm−1, at 100 °K

1972 ◽  
Vol 50 (21) ◽  
pp. 3443-3449 ◽  
Author(s):  
J. E. Bertie ◽  
D. A. Othen
Keyword(s):  
Hydrogen Bonds ◽  
Infrared Spectrum ◽  
Ethylene Oxide ◽  
Infrared Spectra ◽  
Far Infrared ◽  
Empirical Correlation ◽  
Strong Absorption ◽  
Water Molecules ◽  
Oxide Hydrate ◽  
Infrared Frequencies

The infrared spectra of authenticated samples of ethylene oxide hydrate and deuterate at 100 °K have been measured between 360 and 20 cm−1. The spectra confirm that the water molecules are orientationally-disordered and reorient slowly compared to far-infrared frequencies. An empirical correlation is suggested between the frequencies of strong absorption and the number of non-equivalent hydrogen bonds, their length and distribution. The contribution to the spectrum by the ethylene oxide intermolecular vibrations is discussed.

Analysis of the Structures and Thermal Properties of Hexanediamine Adipate and Pentanediamine Adipate

2018 ◽  
Vol 876 ◽  
pp. 76-83
Author(s):  
Xiao Wan Yang ◽  
Xin Min Hao ◽  
Jian Ming Wang ◽  
Yan Bin Liu ◽  
Hong Liang Kang
Keyword(s):  
Thermal Properties ◽  
Melting Point ◽  
Infrared Spectra ◽  
Adipic Acid ◽  
Decomposition Temperature ◽  
Bending Vibration ◽  
Out Of Plane ◽  
Stretching Vibration ◽  
Acid Reaction ◽  
The Difference

Hexanediamine adipate, pentanediamine adipate and bio-based pentanediamine adipate were prepared by adipic acid reaction with 1,6-hexanediamine, 1,5-pentanediamine and bio-based 1,5-pentanediamine, respectively. Their structures and thermal properties have been analyzed by infrared spectra, SEM, DSC and TGA. Infrared spectra showed the main differences between 1,6-hexanediamine and 1,5-pentanediamine for the deformation vibration and out of plane bending vibration of N−H. Hexanediamine adipate and pentanediamine adipate had the difference at the asymmetric stretching vibration of −COO-−. The crystal morphologies of hexanediamine adipate and pentanediamine adipate showed dendritic and acicular, respectively. The melting point of pentanediamine adipate, pentanediamine adipate and bio-based pentanediamine adipate were 208.0 °C, 182.3 °C and 182.9 °C, respectively. The polymerization of hexanediamine adipate, pentanediamine adipate and bio-based pentanediamine adipate happened at 201.0, 190.2 and 194.9 °C, respectively. And the decomposition temperature of PA66, PA56 and bio-based PA56 were 401.8, 403.5 and 405.2 °C, respectively.

Tricarbonyl(η5-formylcyclopentadienyl)manganese(I) and tricarbonyl(η5-formylcyclopentadienyl)rhenium(I) containing short π(CO)...π(CO) and π(CO)...π interactions

2012 ◽  
Vol 68 (3) ◽  
pp. m69-m72 ◽  
Author(s):  
Alexander S. Romanov ◽  
Gary F. Angles ◽  
Mikhail Yu. Antipin ◽  
Tatiana V. Timofeeva
Keyword(s):  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Three Dimensional ◽  
The Other ◽  
Carbonyl Groups ◽  
Π Interactions ◽  
Dimensional Network ◽  
Intermolecular Contacts

The structures of tricarbonyl(formylcyclopentadienyl)manganese(I), [Mn(C6H5O)(CO)3], (I), and tricarbonyl(formylcyclopentadienyl)rhenium(I), [Re(C6H5O)(CO)3], (II), were determined at 100 K. Compounds (I) and (II) both possess a carbonyl group in atransposition relative to the substituted C atom of the cyclopentadienyl ring, while the other two carbonyl groups are in almost eclipsed positions relative to their attached C atoms. Analysis of the intermolecular contacts reveals that the molecules in both compounds form stacks due to short attractive π(CO)...π(CO) and π(CO)...π interactions, along the crystallographiccaxis for (I) and along the [201] direction for (II). Symmetry-related stacks are bound to each other by weak intermolecular C—H...O hydrogen bonds, leading to the formation of the three-dimensional network.

THE INFRARED SPECTRA OF TRIMETHYLAMINE OXIDE SALTS

1963 ◽  
Vol 41 (5) ◽  
pp. 1127-1134 ◽  
Author(s):  
Denys Cook
Keyword(s):  
Hydrogen Bond ◽  
Infrared Spectra ◽  
Field Coupling ◽  
Correlation Field ◽  
Trimethylamine Oxide ◽  
Bending Mode ◽  
Good Agreement

Several salts of trimethylamine oxide have been prepared. A species common to all these salts, the (CH3)3NOH+ ion, has been inferred from the infrared spectra of the solids, but with varying degrees of interaction in the hydrogen bond [Formula: see text] depending on the anion. These variations have been investigated in detail, and with the help of deuterium replacement, confident assignments for the OH stretching, bending, and torsional modes have been made. A splitting of about 80 cm−1 in the bending mode has been noted, and has been ascribed to correlation field coupling. With one exception, the assignments are in good agreement with those previously determined by Giguère and Chin.

scholarly journals Effect of the Hydration Shell on the Carbonyl Vibration in the Ala-Leu-Ala-Leu Peptide

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2148
Author(s):  
Irtaza Hassan ◽  
Federica Ferraro ◽  
Petra Imhof
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Perfect Match ◽  
Hydration Shell ◽  
Interaction Strength ◽  
Bond Distance ◽  
Water Molecules ◽  
Carbonyl Groups ◽  
Bond State

The vibrational spectrum of the Ala-Leu-Ala-Leu peptide in solution, computed from first-principles simulations, shows a prominent band in the amide I region that is assigned to stretching of carbonyl groups. Close inspection reveals combined but slightly different contributions by the three carbonyl groups of the peptide. The shift in their exact vibrational signature is in agreement with the different probabilities of these groups to form hydrogen bonds with the solvent. The central carbonyl group has a hydrogen bond probability intermediate to the other two groups due to interchanges between different hydrogen-bonded states. Analysis of the interaction energies of individual water molecules with that group shows that shifts in its frequency are directly related to the interactions with the water molecules in the first hydration shell. The interaction strength is well correlated with the hydrogen bond distance and hydrogen bond angle, though there is no perfect match, allowing geometrical criteria for hydrogen bonds to be used as long as the sampling is sufficient to consider averages. The hydrogen bond state of a carbonyl group can therefore serve as an indicator of the solvent’s effect on the vibrational frequency.

scholarly journals Crystal structure of 1,7,8,9-tetrachloro-4-(3,5-dichlorobenzyl)-10,10-dimethoxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

2015 ◽  
Vol 71 (1) ◽  
pp. o14-o15
Author(s):  
He Liu ◽  
Jia-liang Zhong ◽  
Wen-xia Sun ◽  
Yan-qing Gong ◽  
Li-hong Liu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Benzene Ring ◽  
Title Compound ◽  
Crystal Packing ◽  
Carbonyl Groups ◽  
Pyrrolidine Ring ◽  
Dipole Interactions ◽  
Compound C

In the title compound, C17H11Cl6NO4, the configuration of the cycloalkene skeleton isendo,cis. The benzene ring is twisted by 58.94 (8)° from the attached pyrrolidine ring. Two carbonyl groups play a key role in the crystal packing. A short intermolecular C...O distance of 3.017 (3) Å reveals that one carbonyl group is involved in dipole–dipole interactions, which link two adjacent enantiomers into an inversion dimer. Another carbonyl group provides an acceptor for the weak intermolecular C—H...O hydrogen bonds which link these dimers into layers parallel to (011).

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