Hydrogen bonding in organic compounds. II. Amine-cabonyl interactions

1958 ◽  
Vol 11 (4) ◽  
pp. 529 ◽  
Author(s):  
AN Hambly ◽  
J Bonnyman
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Organic Compounds ◽  
Aromatic Compounds ◽  
Primary Amine ◽  
Intermolecular Hydrogen Bonding ◽  
Amine Group ◽  
Methyl Anthranilate ◽  
Infra Red ◽  
Related Compounds

A comparison of the infra-red spectra of typical aromatic compounds, with a primary amine group adjacent to a carbonyl group, with the spectra of related compounds, shows that, in the former, weak hydrogen bonding occurs between the two groups. The strength of the bonds formed is in the order : 1-aminoanthraquinone > 2-amino-acetophenone > methyl anthranilate, and the changes in carbonyl frequency are comparable with those of the symmetric NH2 stretching frequency. Stronger hydrogen bonds are formed in corresponding ortho-acetamido compounds. A brief study of the NH2 stretching frequencies of o-nitroamines in dioxan solution shows that there is considerable interaction between solute and solvent but this cannot be definitely attributed to intermolecular hydrogen bonding.

Hydrogen bonding in organic compounds. IX. Intramolecular actions between the primary amine group and amino, nitro, sulphide, and sulphone groups in aromatic compounds

1964 ◽  
Vol 17 (8) ◽  
pp. 860 ◽  
Author(s):  
AN Hambly ◽  
BV O'Grady
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Organic Compounds ◽  
Aromatic Compounds ◽  
Amine Group ◽  
Intermolecular Hydrogen Bonds ◽  
Amino Derivatives ◽  
Stretching Vibrations ◽  
Intramolecular Hydrogen ◽  
Derivatives Of

Spectroscopic evidence for the existence of intermolecular hydrogen bonds between aniline molecules has been obtained. Examples show the existence of intramolecular hydrogen bonds in orthodiamines, some amino-derivatives of heterocycles, 2-nitro-amines, 2-amino-sulphones, and 2-amino-sulphides. Some new observations, which do not agree with Krueger's interpretation of the profile of the overtone bands due to NH2 stretching vibrations, are recorded.

Hydrogen Bonding in organic compounds. 1. o-Nitroanilines

1958 ◽  
Vol 11 (4) ◽  
pp. 513 ◽  
Author(s):  
LK Dyall ◽  
AN Hambly
Keyword(s):  
Hydrogen Bonding ◽  
Nitro Group ◽  
Organic Compounds ◽  
Intramolecular Hydrogen Bonding ◽  
Amino Group ◽  
Infra Red ◽  
Sterically Hindered ◽  
Intramolecular Hydrogen

The infra-red spectra of o-nitroanilines do not indicate any intramolecular hydrogen bonding unless there are nitro groups in both positions 2 and 6 to the amino group. An examination of the literature shows that there is no unambiguous evidence from other sources of such bonding in simple o-nitroanilines. An explanation is given of the variation of the stretching frequencies of the nitro group in sterically hindered compounds and in those with electron-donating ortho- and para-substituents.

scholarly journals 2-Aminoterephthalic acidN,N-dimethylformamide disolvate

2012 ◽  
Vol 68 (8) ◽  
pp. o2501-o2501 ◽  
Author(s):  
Stefan Loos ◽  
Wilhelm Seichter ◽  
Edwin Weber ◽  
Florian Mertens
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Amine Group ◽  
Asymmetric Unit ◽  
Solvent Molecules

The asymmetric unit of the title structure, C8H7NO4·2C3H7NO, contains one 2-aminoterephthalic acid and twoN,N-dimethylformamide molecules. Strong O—H...O hydrogen bonds between the acidic carboxy H atoms of 2-aminoterephthalic acid and the O atoms of both solvent molecules form linear 1:2 complex units. One H atom of the amine group is involved in intramolecular N—H...O hydrogen bonding, whereas the second one takes part in an intermolecular N—H...O connection. Furthermore, the crystal is stabilized by weak C—H...O hydrogen bonds.

ChemInform Abstract: INTRA- AND INTERMOLECULAR HYDROGEN BONDING IN CHLORINATED PHENOLS AND RELATED COMPOUNDS

1975 ◽  
Vol 6 (51) ◽  
Author(s):  
GEORGE C. LEVY ◽  
TADEUSZ HOLAK ◽  
ALOIS STEIGEL
Keyword(s):  
Hydrogen Bonding ◽  
Intermolecular Hydrogen Bonding ◽  
Chlorinated Phenols ◽  
Related Compounds

scholarly journals Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives: synthesis, molecular conformation and hydrogen bonding

2018 ◽  
Vol 74 (12) ◽  
pp. 1783-1789
Author(s):  
Asma ◽  
Balakrishna Kalluraya ◽  
Hemmige S. Yathirajan ◽  
Ravindranath S. Rathore ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Dicarboxylic Acid ◽  
Molecular Conformation ◽  
Three Dimensional ◽  
Framework Structure ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives, one acid, two esters and a dicarbohydrazide have been synthesized starting from 3-aryl sydnones, and structurally characterized. There is an intramolecular O—H...O hydrogen bond in 1-phenyl-1H-pyrazole-3,4-dicarboxylic acid, C11H8N2O4, (I), and the molecules are linked into a three-dimensional framework structure by a combination of O—H...O, O—H...N, C—H...O and C—H...π(arene) hydrogen bonds. In each of the two esters dimethyl 1-phenyl-1H-pyrazole-3,4-dicarboxylate, C13H12N2O4, (II), and dimethyl 1-(4-methylphenyl)-1H-pyrazole-3,4-dicarboxylate, C14H14N2O4, (III), C—H...O hydrogen bonds lead to the formation of cyclic centrosymmetric dimers: in (III), one of the methoxycarbonyl groups is disordered over two sets of atomic sites having occupancies 0.71 (2) and 0.29 (2). An intramolecular N—H...O hydrogen bond is present in the structure of 1-(4-methoxyphenyl)-1H-pyrazole-3,4-dicarbohydrazide, C12H14N6O3, (IV), and the molecules are linked into a three-dimensional framework structure by a combination of N—H...O, N—H...N, N—H...π(arene) and C—H...O hydrogen bonds. Comparisons are made with the structures of a number of related compounds.

scholarly journals Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: 1H-MNR spectroscopic study

2003 ◽  
Vol 68 (1) ◽  
pp. 1-7 ◽  
Author(s):  
R. Markovic ◽  
A. Shirazi ◽  
Zdravko Dzambaski ◽  
Marija Baranac ◽  
Dragica Minic-Popovic
Keyword(s):  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Spectroscopic Study ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Solvent Polarity ◽  
Concentration Effect ◽  
Intermolecular Hydrogen Bonding ◽  
Dynamic 1H Nmr

Application of dynamic 1H-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied.

Hydrogen bonding in 4-nitrobenzene-1,2-diamine and two hydrohalide salts

2014 ◽  
Vol 70 (7) ◽  
pp. 681-688 ◽  
Author(s):  
David K. Geiger ◽  
Dylan E. Parsons
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Nitro Group ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Planar Geometry ◽  
Amine Group ◽  
Acta Cryst ◽  
Extended Structure ◽  
Hydrogen Bonded

The structures of 4-nitrobenzene-1,2-diamine [C6H7N3O2, (I)], 2-amino-5-nitroanilinium chloride [C6H8N3O2+·Cl−, (II)] and 2-amino-5-nitroanilinium bromide monohydrate [C6H8N3O2+·Br−·H2O, (III)] are reported and their hydrogen-bonded structures described. The amine groupparato the nitro group in (I) adopts an approximately planar geometry, whereas themetaamine group is decidedly pyramidal. In the hydrogen halide salts (II) and (III), the amine groupmetato the nitro group is protonated. Compound (I) displays a pleated-sheet hydrogen-bonded two-dimensional structure withR22(14) andR44(20) rings. The sheets are joined by additional hydrogen bonds, resulting in a three-dimensional extended structure. Hydrohalide salt (II) has two formula units in the asymmetric unit that are related by a pseudo-inversion center. The dominant hydrogen-bonding interactions involve the chloride ion and result inR42(8) rings linked to form a ladder-chain structure. The chains are joined by N—H...Cl and N—H...O hydrogen bonds to form sheets parallel to (010). In hydrated hydrohalide salt (III), bromide ions are hydrogen bonded to amine and ammonium groups to formR42(8) rings. The water behaves as a double donor/single acceptor and, along with the bromide anions, forms hydrogen bonds involving the nitro, amine, and ammonium groups. The result is sheets parallel to (001) composed of alternatingR55(15) andR64(24) rings. Ammonium N—H...Br interactions join the sheets to form a three-dimensional extended structure. Energy-minimized structures obtained using DFT and MP2 calculations are consistent with the solid-state structures. Consistent with (II) and (III), calculations show that protonation of the amine groupmetato the nitro group results in a structure that is about 1.5 kJ mol−1more stable than that obtained by protonation of thepara-amine group. DFT calculations on single molecules and hydrogen-bonded pairs of molecules based on structural results obtained for (I) and for 3-nitrobenzene-1,2-diamine, (IV) [Betz & Gerber (2011).Acta Cryst.E67, o1359] were used to estimate the strength of the N—H...O(nitro) interactions for three observed motifs. The hydrogen-bonding interaction between the pairs of molecules examined was found to correspond to 20–30 kJ mol−1.

Intra- and intermolecular hydrogen bonding in chlorinated phenols and related compounds

1975 ◽  
Vol 79 (21) ◽  
pp. 2325-2327 ◽  
Author(s):  
George C. Levy ◽  
Tadeusz Holak ◽  
Alois Stelgel
Keyword(s):  
Hydrogen Bonding ◽  
Intermolecular Hydrogen Bonding ◽  
Chlorinated Phenols ◽  
Related Compounds

scholarly journals Charge Transfer on the Surface-Enhanced Raman Scattering of Ag/4-MBA/PEDOT:PSS Syste: Intermolecular Hydrogen Bonding

Chemosensors ◽  
2021 ◽  
Vol 9 (5) ◽  
pp. 111
Author(s):  
Yuenan Pan ◽  
Wei Wang ◽  
Shuang Guo ◽  
Sila Jin ◽  
Eungyeong Park ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Hydrogen Bonds ◽  
Raman Scattering ◽  
Surface Enhanced Raman Scattering ◽  
Sers Substrate ◽  
Intermolecular Hydrogen Bonding ◽  
Surface Enhanced ◽  
Surface Enhanced Raman ◽  
Enhanced Raman Scattering

A sandwich-structured noble metal-probe molecule-organic semiconductor consisting of Ag nanoparticles (NPs), 4-mercaptobenzoic acid (4-MBA) and different concentrations of poly(styrenesulfonate:poly(3,4-ethylenedioxythiophene) (PEDOT:PSS) was prepared by layer-by-layer assembly. Intermolecular hydrogen bonding was observed to have a significant effect on the surface-enhanced Raman scattering (SERS) of Ag/4-MBA/PEDOT:PSS. Upon increasing the PEDOT:PSS concentration, the characteristic Raman band intensity of 4-MBA was enhanced. In addition, the selected b2 vibration mode was significantly enhanced due to the influence of the charge transfer (CT) mechanism. The CT degree (ρCT) of the composite system was calculated before and after doping with PEDOT:PSS; when the concentration of PEDOT:PSS was 0.8%, the SERS intensity tended to be stable, and ρCT reached a maximum. Compared with that of the undoped PEDOT:PSS system, ρCT was significantly enhanced after doping, which can be explained by the CT effect induced by hydrogen bonds. These results indicate that hydrogen bonding transfers a charge from the Fermi energy level of Ag to the lowest unoccupied molecular orbital (LUMO) of 4-MBA, and due to the resulting potential difference, the charge will continue to transfer to the LUMO of PEDOT:PSS. Therefore, the introduction of organic semiconductors into the field of SERS not only expands the SERS substrate scope, but also provides a new idea for exploring the SERS mechanism. In addition, the introduction of hydrogen bonds has become an important guide for the study of CT and the structure of composite systems.

HYDROGEN BONDING IN THE AMINE HYDROHALIDES: II. THE INFRARED SPECTRUM FROM 4000 TO 2200 CM−1

1960 ◽  
Vol 38 (1) ◽  
pp. 34-44 ◽  
Author(s):  
C. Brissette ◽  
C. Sandorfy
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Infrared Spectrum ◽  
Infrared Spectra ◽  
Primary Amine ◽  
Lithium Fluoride ◽  
Aliphatic Amine ◽  
Combination Bands ◽  
Lower Frequencies ◽  
Amine Salts

The infrared spectra of a number of amine hydrohalides have been measured in the lithium fluoride region.Hydrogen bonding and the torsional oscillations of the [Formula: see text] groups influence these spectra characteristically. The [Formula: see text] stretching frequencies give broad or fairly broadbands. They are near 3000 cm−1 for aliphatic primary amine salts. The corresponding band lies at somewhat lower frequencies for secondary amine salts and much lower for tertiary ones. The aromatic amine hydrohalides exhibit these bands at lower frequencies than do the aliphatic amine salts of the same order. There is a shift to higher frequencies in the series hydrochloride, hydrobromide, hydriodide.All these spectra contain a number of sharper bands which may or may not coincide with the hydrogen-bonded stretching bands. These are combination bands involving mainly deformation vibrations, and they shift to lower frequencies, throughout the series hydrochloride, hydrobromide, hydriodide.The importance of electrical anharmonicity for the appearance of these bands is stressed.The hydrogen bonds in amine hydrohalides appear to be largely electrostatic in character.

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