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.

β-Amino ketoximes: a study of basicity, hydrogen bonding and isomerism

1977 ◽  
Vol 30 (7) ◽  
pp. 1467 ◽  
Author(s):  
HK Powell ◽  
JM Russell
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Calorimetric Data ◽  
Amino Groups ◽  
Or Groups ◽  
Inductive Effects ◽  
Methylene Groups ◽  
Secondary Amino ◽  
Intramolecular Hydrogen ◽  
Cis And Trans

The protonation reactions of the diamine dioxime 4,4,9,9-tetramethyl- 5,8-diazadodecane-2,11-dione dioxime and its O-methyl and bis-O-methyl ethers have been studied at 25�, I 0.10 M NaCl. The (substituted) oxime groups cause a marked reduction in the basicity of the secondary amino groups. log K (potentiometric) and ΔH (calorimetric) data are interpreted in terms of inductive effects of the oxime group and possible intramolecular hydrogen bonding, N+-H...N(OR)=, pKa for methoxy-amine, NH2OMe, has been determined (4.62�0.01, I 0.10 M NaCl, 25�). ������ P.m.r. spectra are assigned for β-amino ketoximes having α- methyl and α-methylene groups cis and trans to =N-OR groups. Infrared spectra are reported.

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.

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.

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].

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.

Theoretical study of intramolecular hydrogen bonding and molecular geometry of 2-trifluoromethylphenol

10.1002/jcc.2 ◽  
1996 ◽  
Vol 17 (16) ◽  
pp. 1804-1819 ◽  
Author(s):  
Attila Kov�cs ◽  
Istv�n Kolossv�ry ◽  
G�bor I. Csonka ◽  
Istv�n Hargittai
Keyword(s):  
Hydrogen Bonding ◽  
Theoretical Study ◽  
Molecular Geometry ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen

Intramolecular Hydrogen Bonding Facilitates Electrocatalytic Reduction of Nitrite in Aqueous Solutions

2019 ◽  
Vol 58 (14) ◽  
pp. 9443-9451 ◽  
Author(s):  
Song Xu ◽  
Hyuk-Yong Kwon ◽  
Daniel C. Ashley ◽  
Chun-Hsing Chen ◽  
Elena Jakubikova ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Aqueous Solutions ◽  
Intramolecular Hydrogen Bonding ◽  
Electrocatalytic Reduction ◽  
Intramolecular Hydrogen
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