Hydrogen bonding and substituent group effects in phenols. Part II. Apparent dipole moments and infrared spectra of N-(4-substituted benzylidene)-4-hydroxyanilines in benzene, carbon tetrachloride, and dioxan

1971 ◽  
pp. 864
Author(s):  
D. C. Colinese
Keyword(s):  
Hydrogen Bonding ◽  
Carbon Tetrachloride ◽  
Infrared Spectra ◽  
Dipole Moments ◽  
Substituent Group ◽  
Group Effects

THE INFRARED CARBONYL STRETCHING BANDS OF RING SUBSTITUTED ACETOPHENONES

1957 ◽  
Vol 35 (5) ◽  
pp. 504-514 ◽  
Author(s):  
R. Norman Jones ◽  
W. F. Forbes ◽  
W. A. Mueller
Keyword(s):  
Carbon Tetrachloride ◽  
Infrared Spectra ◽  
Aromatic Nucleus ◽  
Carbon Tetrachloride Solution ◽  
Substituent Group ◽  
Acetophenone Derivatives

An examination has been made of the carbonyl stretching bands in the infrared spectra of acetophenone derivatives substituted in the aromatic nucleus. The positions, integrated absorption intensities, and widths of the bands have been measured in carbon tetrachloride solution. The variation of these quantities is discussed in relation to the nature and position of the substituent group.

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.

Solvent Effect on the Structure and Infrared Spectra of N-(3-Chloro-2-benzo[b]thienocarbonyl)-N'-ethylthiourea

1996 ◽  
Vol 61 (11) ◽  
pp. 1620-1626 ◽  
Author(s):  
Oľga Hritzová ◽  
Gejza Suchár ◽  
Ivan Danihel ◽  
Peter Kutschy
Keyword(s):  
Hydrogen Bonding ◽  
Solvent Effect ◽  
Infrared Spectra ◽  
Title Compound ◽  
Dipole Moments ◽  
Intramolecular Hydrogen Bonding ◽  
Spatial Arrangement ◽  
Intramolecular Hydrogen ◽  
Ir Bands

The solvent effect on the title compound was studied by examining changes in the positions of IR bands belonging to the NH and CO bonds and in the dipole moments in benzene and dioxane solutions. The results are discussed in terms of intramolecular hydrogen bonding and spatial arrangement of the CONHCSNH grouping.

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.

The chemistry of aliphatic unconjugated nitramines. II. Intramolecular properties and crystal packing

1969 ◽  
Vol 22 (12) ◽  
pp. 2505 ◽  
Author(s):  
J Stals
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Packing ◽  
Dipole Moments ◽  
Molecular Crystals ◽  
Bond Orders ◽  
Bond Energies ◽  
Electric Dipole Moments ◽  
Charge Distributions ◽  
Hydrogen Bonding Interactions ◽  
Vb Structures

The VESCF(BJ)-MO electric dipole moments, molecular ionization potentials, electronic bond energies, charge distributions, and bond orders for nitramide, N-methylnitramine, and s- and as-N,N- dimethylnitramines are reported. The packing of nitramide, RDX, and HNX in their molecular crystals is rationalized in terms of electrostatic and hydrogen-bonding interactions. Simple VB structures do not readily predict their calculated MO charge distributions and bond orders.

Infrared spectra of aqueous sodium benzoates and salicylates in the carboxyl-stretching region: chelation in aqueous sodium salicylates

1969 ◽  
Vol 47 (24) ◽  
pp. 4577-4588 ◽  
Author(s):  
G. E. Dunn ◽  
R. S. McDonald
Keyword(s):  
Salicylic Acid ◽  
Carbon Tetrachloride ◽  
Infrared Spectra ◽  
Aromatic Compounds ◽  
Deuterium Oxide ◽  
Substituent Effects ◽  
Good Evidence ◽  
Frequency Region ◽  
Aqueous Sodium ◽  
Substituent Constants

Infrared spectra in the frequency region 1300–1760 cm−1 are reported for 41 substituted sodium benzoates and 10 substituted sodium salicylates in deuterium oxide solution, and for 9 substituted salicylic acids in chloroform and carbon tetrachloride solutions. Carboxylate stretching frequencies of benzoates and salicylates correlate poorly with substituent constants, but the asymmetric frequencies of benzoates and salicylates correlate well with each other, and the asymmetric frequencies of benzoates correlate well with the asymmetric frequencies of the corresponding nitrobenzenes. It is suggested that, among substituted aromatic compounds, group vibrations which couple with the ring vibrations may correlate well with similar vibrations of other groups, but not with coupled vibrations of different symmetry, uncoupled vibrations, or substituent constants. Chelation in chloroform solutions of salicylic acid dimers can be detected by its influence on substituent effects, but infrared spectra provide no good evidence for chelation in aqueous sodium salicylates.

Molecular Association of Hydrogen Bonding Solutes, o-, m-, and p-Cresol, in Carbon Tetrachloride

1974 ◽  
Vol 52 (4) ◽  
pp. 653-660 ◽  
Author(s):  
Earl M. Woolley ◽  
Dennis S. Rushforth
Keyword(s):  
Hydrogen Bonding ◽  
Carbon Tetrachloride ◽  
Least Squares ◽  
Molecular Association ◽  
Intermolecular Hydrogen Bonding ◽  
Heats Of Dilution ◽  
Self Association

The intermolecular hydrogen-bonding self-association of the three cresols in CCl4 solutions at 25 °C has been investigated by calorimetric means. Calorimetrically determined heats of dilution of each of the cresols in anhydrous CCl4 are interpreted in terms of two different models: (i) dimerization and trimerization self-association reactions, and (ii) dimerization followed by stepwise polymerization self-association reactions. Values of K, ΔH0, and ΔS0 for these reactions are calculated using least-squares and other methods. Results show that o-cresol is clearly less associated in anhydrous CCl4 solution at 25 °C than either m- or p-cresol. Values of K2 and K3 (both based on molar concentrations of solutes) and ΔH20and ΔH30 (kcal) for the reactions [Formula: see text] respectively, are o-cresol: 0.7, 1.3,−3.4,−12.5; m-cresol: 0.8, 5.0,−5.0,−13.6; p-cresol: 0.35, 6.5,−5.5,−13.4. Values of K2 and Ks (both based on molar concentrations of solutes) and ΔH20 and ΔHs0 (kcal) for the reactions [Formula: see text] (all n > 2 with same Ks and ΔHS0), respectively, are o-cresol: 0.7, 1.6, −4.2, −4.5; m-cresol: 1.2, 4.0, −5.0, −4.3; p-cresol: 1.0, 7.0, −3.3, −3.5.

Dipole moments, Kerr constants and solution-state conformations of di(pyridin-4-yl), di(pyridin-3-yl) and di(pyridin-2-yl) ketone

1980 ◽  
Vol 33 (12) ◽  
pp. 2597 ◽  
Author(s):  
PH Gore ◽  
IG John ◽  
RK Pierens ◽  
GLD Ritchie
Keyword(s):  
Carbon Tetrachloride ◽  
Dipole Moments ◽  
Strong Preference ◽  
Trans Conformation ◽  
Solution State ◽  
Kerr Constants

Experimental dipole moments and molar Kerr constants are reported and analysed for di(pyridin-4-yl), di(pyridin-3-yl) and di(pyridin-2-yl) ketone as solutes in carbon tetrachloride or cyclohexane at 298 K. The preferred conformation of di(pyridin-4-yl) ketone is found to be very similar to those previously deduced for benzophenone and several 4,4'- disubstituted benzophenones. For di(pyridin-3-yl) and di(pyridin-2-yl) ketone three analogous conrotatory structures having different relative dispositions of the nitrogen atoms are considered. In the case of di(pyridin-3-yl) ketone the cis-trans and trans-trans arrangements are approximately equally abundant, but for di(pyridin-2-yl) ketone there is a strong preference for the trans-trans conformation.

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