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.

Intramolecular Hydrogen Bonding in Mononitronaphthylamines

1960 ◽  
Vol 13 (4) ◽  
pp. 456
Author(s):  
A Bryson ◽  
RL Werner
Keyword(s):  
Hydrogen Bonding ◽  
Carbon Tetrachloride ◽  
Intramolecular Hydrogen Bonding ◽  
Amino Group ◽  
Amino Groups ◽  
Solute Interaction ◽  
Intramolecular Hydrogen

The presence of intramolecular hydrogen bonding in 2-nitro-1-naphthylamine, 1-nitro-2-naphthylamine, 3-nitro-2-naphthylamine, and 8-nitro-1-naphthylamine is inferred from a study of the NH frequencies of the 14 isomeric mononitronaphthylamines in the solvents carbon tetrachloride and pyridine. The NH stretching frequencies are decreased in pyridine as a result of hydrogen bonding between the amino group and the solvent. The extent of this decrease is quite uniform for all nitronaphthylamines except those in which the nitro and amino groups are adjacent, and in these cases the decrease is about half that observed from the remaining compounds. This is interpreted as indicating the presence of intramolecular hydrogen bonding in the latter group, the extent of which reduces the degree of solvent-solute interaction.

N.M.R. and absorption spectra of nitrotoluidines

1974 ◽  
Vol 27 (4) ◽  
pp. 915 ◽  
Author(s):  
T Yokoyama
Keyword(s):  
Hydrogen Bonding ◽  
Absorption Band ◽  
Nitro Group ◽  
Absorption Spectra ◽  
Long Range ◽  
Chemical Shifts ◽  
Intramolecular Hydrogen Bonding ◽  
Polar Solvents ◽  
Dimethylamino Group ◽  
Intramolecular Hydrogen

N.m.r. chemical shifts of ring protons and absorption spectra of 4-substituted 2-nitroaniline deriva- tives were investigated. It was ascertained that the rotations of dimethylamino and/or 2-nitro groups are influenced by the resonance interaction of the dimethylamino group with 4-substituents and the C1 → C2 absorption band is displaced bathochromically by resonance saturation with 4-substituents. The long-range coupling of NH with H5 in N-methyl-2-nitro-p-toluidine was found to be absent and it is considered that the intramolecular hydrogen bonding of amino hydrogen with the 2-nitro group is ruptured by ROH and polar solvents.

An Infra-Red Study of the Association of Diazoaminobenzene

1960 ◽  
Vol 13 (2) ◽  
pp. 230
Author(s):  
LK Dyall
Keyword(s):  
Hydrogen Bonding ◽  
Equilibrium Constant ◽  
Linear Relation ◽  
Intramolecular Hydrogen Bonding ◽  
Dimer Formation ◽  
Frequency Shifts ◽  
Infra Red ◽  
Intramolecular Hydrogen

The infra-red spectrum of diazoaminobenzene reveals that dimeric association occurs through hydrogen bonding. In tetrachloroethylene solution, the equilibrium constant for dimer formation is found to be 1.2�0.2 1 mol-1. The effects of various solvents on the free N-H stretching frequency have been examined, and the frequency shifts are linearly related to those reported by Bellamy and Hallam (1959) for pyrrole. A linear relation of this type is also found for %nitroaniline, and confirms that there is no significant intramolecular hydrogen bonding in this compound.

scholarly journals Studies on Succinic Acids. IV. Evidence for the Existence of Intramolecular Hydrogen Bonding in Certain Highly Alkylated Succinic Acids by Infra-Red Spectra.

1959 ◽  
Vol 13 ◽  
pp. 224-235 ◽  
Author(s):  
Lennart Eberson ◽  
Knut Asbjørn Straumsgard ◽  
Svend E. Hansen ◽  
R. Sömme ◽  
Einar Stenhagen ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Infra Red ◽  
Intramolecular Hydrogen

scholarly journals Ethyl 4-anilino-2,6-bis(4-fluorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

2013 ◽  
Vol 69 (2) ◽  
pp. o299-o300 ◽  
Author(s):  
Sumati Anthal ◽  
Goutam Brahmachari ◽  
Suvankar Das ◽  
Rajni Kant ◽  
Vivek K. Gupta
Keyword(s):  
Hydrogen Bonding ◽  
Dihedral Angle ◽  
Title Compound ◽  
Intramolecular Hydrogen Bonding ◽  
Boat Conformation ◽  
Amino Group ◽  
Π Interactions ◽  
Compound C ◽  
Intramolecular Hydrogen

In the title compound, C32H28F2N2O2, the tetrahydropyridine ring adopts a distorted boat conformation. The two fluorophenyl groups are attached to the tetrahydropyridine ring in atransorientation. The dihedral angle between the planes of the fluoro-substituted rings is 57.0 (1)°. The amino group and carbonyl O atom are involved in intramolecular hydrogen bonding. In the crystal, weak C—H...O, C—H...F and C—H...π interactions link the molecules into columns along [010].

Sign in / Sign up

Export Citation Format

Share Document