Synthesis and characterization of N-Chloro-o-nitroanilines

1976 ◽  
Vol 29 (2) ◽  
pp. 367 ◽  
Author(s):  
KJ Chapman ◽  
LK Dyall
Keyword(s):  
Hydrogen Bonding ◽  
Carbon Tetrachloride ◽  
Infrared Spectra ◽  
Acid Catalysis ◽  
Intramolecular Hydrogen Bonding ◽  
Synthesis And Characterization ◽  
Catalysed Reaction ◽  
Lone Pairs ◽  
Intramolecular Hydrogen

Chlorine(1) oxide in carbon tetrachloride was found to be an effective reagent for N-chlorinating 2-nitroanilines. These N-chloro-2-nitroanilines are sufficiently stable in solution at 20� to be characterized by reduction and by proton n.m.r, and infrared spectra. The infrared N-H stretching frequencies fall near the low value of 3330 cm-1, apparently because of interaction between N-H bond and chlorine lone pairs; there are also effects of intramolecular hydrogen bonding and of conformation. Under acid catalysis, N-chloro-2-nitroaniline rearranges to C-chlorinated 2-nitroanilines, while with alkali it cyclizes to benzofuroxan. The acid-catalysed reaction has the same features as the Orton rearrangement of N-chloroacetanilides.

Sporidesmins. XVIII. The Infrared Solution Spectra (4000-1600 cm-1) of Sporidesmin, Sporidesmin-B, Sporidesmin-D and Sporidesmin-E

1981 ◽  
Vol 34 (6) ◽  
pp. 1215 ◽  
Author(s):  
J Ronaldson
Keyword(s):  
Hydrogen Bonding ◽  
Carbon Tetrachloride ◽  
Hydroxy Group ◽  
Infrared Spectra ◽  
Intramolecular Hydrogen Bonding ◽  
Disulfide Bridge ◽  
Molecular Models ◽  
Intramolecular Hydrogen

The solution infrared spectra of sporidesmin, sporidesmin-B, sporidesmin-D and sporidesmin-E have been determined in carbon tetrachloride. Though these compounds differ only slightly in structure, their spectra show marked differences which indicate differences in the intramolecular hydrogen bonding. These differences have been related to the known structures by using molecular models. ��� In the v(OH) region, the spectra for sporidesmin-B and sporidesmin-E are similar, though the former compound has only one hydroxy group and the latter an epitrithio group. The spectrum for sporidesmin-D reflects the relaxation of the strain arising from the disulfide bridge in sporidesmin. ��� The non-bonded carbonyls absorb at 1685-1718 cm-1 and the corresponding bonded carbonyls absorb at 1657-1680 cm-1. The Δv(C0) was greatest in sporidesmin-E. ��� In the C-H stretching region, the spectra are similar except for sporidesmin-D where there are the extra absorptions for the two S- methyls. ��� The instability of sporidesmin-E is discussed.

scholarly journals Crystallographic and spectroscopic characterization of 3-chloro-5-fluorosalicylaldehyde

2020 ◽  
Vol 76 (12) ◽  
pp. 1810-1812
Author(s):  
Christopher T. Triggs ◽  
Joseph M. Tanski
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
Intramolecular Hydrogen Bonding ◽  
Spectroscopic Characterization ◽  
Face To Face ◽  
Π Stacking ◽  
Intramolecular Hydrogen

The title compound (systematic name: 3-chloro-5-fluoro-2-hydroxybenzaldehyde), C7H4ClFO2, is a dihalogenated salicylaldehyde derivative that has been studied for its antibacterial characteristics. The salicylaldehyde engages in intramolecular hydrogen bonding with an O—H...O distance of 2.6231 (19) Å while the molecules pack together via weak intermolecular C—H...O, C—H...F and F...O interactions and offset face-to-face π-stacking.

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.

Infrared Study of Some Oxalamidines

1965 ◽  
Vol 19 (2) ◽  
pp. 48-51 ◽  
Author(s):  
Vasile P. Macovei ◽  
D. W. Robinson
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectra ◽  
Intramolecular Hydrogen Bonding ◽  
Solution Concentration ◽  
Infrared Study ◽  
Vibrational Bands ◽  
Intramolecular Hydrogen

Infrared spectra of various aromatic-substituted oxalamidines have been obtained. The behavior of the vibrational bands originating in the amidine groupings as a function of solution concentration is interpreted as indicating the presence of persistent intramolecular hydrogen bonding.

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY SPECTROSCOPIC METHODS: PART VII. INTRAMOLECULAR HYDROGEN BONDING AND STERIC INTERACTIONS IN o-NITROBENZALDEHYDE AND RELATED COMPOUNDS

1962 ◽  
Vol 40 (10) ◽  
pp. 1891-1898 ◽  
Author(s):  
W. F. Forbes
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Infrared Spectra ◽  
Intramolecular Hydrogen Bonding ◽  
Spectroscopic Methods ◽  
Steric Interactions ◽  
Spectral Changes ◽  
Suitable Reference ◽  
Intramolecular Hydrogen ◽  
Related Compounds

Certain unusual features in the infrared spectra of o-nitrobenzaldehyde have been interpreted either in terms of an intramolecular hydrogen bond or in terms of steric interactions. As an extension of these studies we have investigated the ultraviolet, infrared, and n.m.r. spectra of o-nitrobenzaldehyde and of suitable reference compounds and have re-examined the available other evidence. It is concluded that the observed spectral changes can best be explained in terms of steric interactions rather than in terms of intramolecular hydrogen bonding.

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